Before denim shorts and white trainers take over your wardrobe with another warm spell on the horizon, might I suggest considering a more elevated alternative?

Stepping out in one of the chicest warm-weather outfits I've spotted this season, Cindy Crawford swapped her usual denim for a pair of tailored trousers in an elegant shade of beige. Lighter than their denim counterparts and therefore far better suited to rising temperatures, these polished trousers offer all the ease of jeans whilst delivering a much more refined finish.

Styled simply with a classic tank top and sunglasses, had Cindy reached for blue jeans instead, the outfit would have felt considerably more casual; the tailored silhouette brings a sophistication that simple ensembles feel much more intentional.

In another inspired styling move, Crawford skipped predictable white trainers in favour of delicate strappy sandals. Whilst trainers will always earn their place during days packed with walking, they rarely look quite as elegant as a sleek sandal. Together, the tailored trousers and minimal sandals create a simple foundation that feels easy yet polished.

Feeling inspired? Read on to shop my edit of the best Cindy-approved thong sandals below.

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This summer, I’m moving away from classic blue jeans in favour of a more interesting denim trend. Khaki jeans have been cropping up everywhere recently, and this week Cindy Crawford made a strong case for the versatile neutral.

Wearing a dark khaki pair, Crawford styled the trending jeans with a pretty white blouse and suede heeled sandals for a look that felt simple, elegant and easy to wear. The softer tone of the denim gave the outfit a more elevated feel than classic blue jeans, while still keeping it relaxed enough for daytime styling.

It’s also an especially practical option for summer. While blue jeans can sometimes feel overly casual and black denim can look too heavy in warmer weather, khaki jeans sit comfortably in between. Neutral, versatile and easy to style, they work just as well during the day as they do for evening plans.

Keeping to a palette of earthy neutrals, Crawford finished the outfit with a beige tote bag and a white leather jacket, pulling together a timeless look that won’t quickly date.

If your denim rotation is feeling a little too blue-heavy right now, consider this your sign to try khaki jeans this season.

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More so than ever before has the concept of taste been mired in discourse. To me, however, the notion of possessing great taste is akin to having enough life experience to distinguish between something that’s trending, passé, or pastiche, and to know the precise contexts that suit each best. So, when it comes to fashion, that’s why I always look to those slightly older than myself for inspiration.

This summer, specifically, I’m turning to a set of over-50s style savants for guidance on how to dress, using their personal sartorial philosophies as a lens to filter out anything that could easily date, appear trite or simply convey that I’m replicating some niche aesthetic espoused as “in” on the internet.

As far as seasons go, those over 50 really do summer trends best. In part because they’ve had close to five decades to cultivate and hone a wardrobe that complements them, but also because the warm weather invites a more minimalistic approach that’s more in keeping with how many quinquagenarians like to dress.

Whilst many Gen Zers like myself often find ourselves asking tedious questions when putting together an ensemble to ensure what we wear reflects our self-expression—like whether this piece of clothing is truly “me”—those over 50 tend to be less pensive. With more impulsivity and spontaneity, their looks are instilled with a sense of quiet confidence and effortless elegance.

Still, if you’re looking for practical tips from this cohort, there’s a lot to be gleaned. The primary lesson is to never overlook the power of a solid basic, which is something the likes of Cindy Crawford and Jennifer Aniston have proved time and time again with their adoration for a pair of sturdy denim jeans and crisp white t-shirts.

Because, ultimately, the bona fide way to express that you have good taste is to study the masters, learn their techniques and apply what resonates with you most. Miuccia Prada said it best when she said, “Study, study, study. Learn, watch movies, look at art, read literature.” Or, in this case, scroll through for a comprehensive breakdown of the 6 key summer trends those over 50s will be wearing all season long.

6 Chic Over 50s Summer 2026 Fashion Trends

1. White Skirts

Style Notes: White skirts have been a mainstay in summer for nearly a century. Though the calf-grazing length can sometimes feel a bit matronly—perhaps due to its connotations with nurse uniforms, which is a trope Prada reinforced in its autumn/winter 2023 collection—stars like Demi Moore and former J.CREW creative director, Jenna Lyons is proving just how versatile the trend is this season. Pair with everything from a ribbed tank top and suede ballet flats to structured tailoring and oversized sunglasses.

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2. Dark Wash Jeans

Style Notes: Though the natural inclination when the temperature rises is to wear lighter hues that match this climatic mood, stars like Tracee Ellis Ross are making a case for subverting the norm. Indeed, opting for dark-wash jeans rendered in rich-looking indigo shade, like the Pattern Beauty founder has for Dior’s recent Cruise 2027 collection presentation in Los Angeles, adds a depth and sense of intrigue to your look. Plus, for moments when monochrome, all-black dressing starts to wane, this colour scheme offers a point of difference, while still retaining the same qualities.

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3. Royal Purple Hues

Style Notes: In a similar vein, royal purple palettes have become one of the most commanding colours of summer. This makes sense considering it’s the scion of two of the biggest shades of the year (tomato red and cobalt blue), but for those after something a little more enigmatic while still capturing the trend cycle, this colour does it all. Already traipsing down the runway, from magnetic plums at Prada to vibrant violets at Balenciaga, follow in suit through sheer touches, lightweight knits and functional base layers.

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4. Oversized Shirting

Style Notes: The button-down shirt is fashion’s workhorse. Dependable, practical and often overlooked, this is a staple that serves as the canvas for so many looks, whether it be something more proper for office settings or deliciously languid for holidays. This summer, the stylish over-50s are thrusting it back into the spotlight. Perennially appealing with a loose-cut insouciance, style with stovepipe jeans and slingbacks or that white skirt you picked up earlier in the article.

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5. Classic LBDs

Style Notes: To have great taste is to invest in something that will only get better with time. Such is the case with the classic little black dress. Though not specifically a trend, given its universal appeal and timeless status, it is a silhouette that’s currently garnering interest again. Blame it on Mattheiu Blazy turning our attention back to Gabrielle Chanel and the origins of the house, but this renewed attraction only serves to prove how enduring and chic this style is. Wear at long al fresco lunches, casual days perusing vintage boutiques or evening soirees.

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6. Basket Bags

Style Notes: With age comes wisdom, like the knowledge that sometimes investing in a humble basket bag is just as sufficient as purchasing the latest designer bag. At least, that is the case for some of the most stylish over-50s, choosing to go down the path paved by Jane Birkin in the ‘60s. More subtle and refined, be it raffia or woven leather, these basket bags add a charming touch and Côte d'Azur breeziness that’s so essential for summer.

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Between jelly sandals, Carolyn Bessette-Kennedy-inspired fashion and statement cord necklaces, it feels like the ‘90s are officially back. But let’s be honest, this iconic decade has never really left us. But it’s undeniably more evident in 2026. And if there’s one nineties category that made the biggest mark this year, it would certainly have to be beauty. More specifically, '90s makeup looks are making a huge comeback this year, with some of the biggest trends being those we saw dominate almost four decades ago.

Now, we know that makeup trends come and go, especially in the age of TikTok, Instagram and YouTube, but there’s just something about a ‘90s makeup look that feels timeless, fitting right into the current zeitgeist without a second thought. Of course, there are trends that, as a makeup minimalist, would have had me running in the opposite direction: body glitter, bright blue eyeshadow and face gems, to name a few. But luckily for me, the it-girl-approved ‘90s makeup trends making a comeback in 2026 remain chic, timeless and, most importantly, feel extremely wearable.

Below, I’ve rounded up the seven key ‘90s makeup aesthetics that are set to dominate 2026. From playful pops of colour that are perfect for the upcoming summer season to the dark lip-liner trend that’s taken TikTok by storm, keep scrolling to see the ‘90s makeup looks trends that are making a comeback in 2026, plus the best beauty buys available so that you can get the look at home.

1. Statement Red Lip

We can't talk about '90s makeup without talking about a bold red lip. Unlike in the current day and age, when it's often paired with equally eye-catching smoky eyeshadows and statement blushes, in the ‘90s it was all about keeping the rest of the face pared-back and minimal, so as to let the lips do the talking (pun intended).

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2. Colour Pop

Vivid eyes, cheeks and lips were certainly all the rage in the '90s, and I can see why. These playful colour pops take a makeup routine from basic to elevated, and although I’m not ready to go all out with the trend, this pretty pinky-purple look on Naomi Campbell is slowly convincing me to try it out.

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3. Frosted

With “cold-girl makeup,” one of TikTok's latest obsessions, it should come as no surprise that the frosty aesthetic is making a comeback this year. Available in the form of everything from lipsticks to eyeshadows to highlighters, this icy makeup trend perfectly balances feeling cool and classic.

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4. Ultra-Matte

As someone with extremely dry skin, I’ve always been skeptical about recreating the ultra-matte bases that dominated the mid-90s. However, there are now plenty of products that give that blurring effect without sucking out every bit of moisture from the skin. So, I’m ready to give this long-lasting, sophisticated look a try.

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5. Dark Lip Liner

I’m not trying to brag, but I’ve been rocking the dark lip liner trend since I was a young teen. Between ultra matte blacks, cool-toned browns and deep burgundy hues, this is a trend that I can guarantee will never date.

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6. Ultra-Thin Brows

If you have thin eyebrows as I do, then you’ll be pleased to know that the ultra-thin brow trend, championed by the likes of Victoria Beckham, is officially back for 2026.

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7. Smoky Eye

For those more formal occasions, there’s nothing quite like a smokey eye. Although this mesmerising eyeshadow look has technically never stopped trending, I, for one, will be taking a cue from the likes of ‘90s icons such as Cindy Crawford and recreating this more subtle look for summer evenings out.

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There’s never been a better time to be a product of the ‘90s than right now. Carolyn Bessette Kennedy’s subtly sophisticated ensembles are back in the spotlight, Posh Spice is making her trademark sharp tailoring more accessible than ever through her collaboration with high-street giant Gap, jelly sandals have become the acme of luxury, and Practical Magic is heading back to the big screen with a highly anticipated witchy sequel.

Of course, that’s not even mentioning the breadth of sartorial moments that are staging a comeback. From pencil skirts seen all over the Chanel runway and in the new season collections of defiantly minimal brands like St. Agni to the return of Galliano-for-Dior-esque lace-trim slip dresses, it seems that everything old is new again.

Still, if there was one fashion category that was making the biggest mark this spring, it would certainly have to be denim. Specifically, ‘90s jeans trends are making a roaring return this year, with some of the biggest silhouettes being the ones that were most popular close to three decades ago.

Leading the pack is none other than stovepipe jeans. Sharp, polished and cut close to the body, this elongating trouser style was a favourite of supermodels off duty like Cindy Crawford and Christy Turlington and has now been adopted by contemporary style savants, including Alexa Chung and Kendall Jenner.

Their appeal lies in their innate elegance, architectural nature and versatility in styling. Slip into a pair, and you’ll find any spring jacket—though bonus points are awarded if the piece is more ornate, like the floral embroidered and opera-inspired styles seen at Valentino, Conner Ives and Viktor Gichev—appears more elevated than ever.

Elsewhere across fashion capitals, perennially functional bootcut jeans is piquing interest. Of course, the most obvious companion to your favourite pair of knee-high, heeled leather boots, but they also make a worthy partner to sleek ballet pumps, heeled sandals and satin trousers. And when it’s a style that’s been endorsed by the likes of Kate Moss and Gwyneth Paltrow for years—and now a cornerstone of Bella Hadid and Hailey Bieber’s wardrobe—what’s not to like?

The most surprising ‘90s jeans trend to come back this spring, however, would have to be cuffed jeans. With an exposed hem and ankle-grazing cut, this style is actually the most democratic of the bunch, given its ability to transform any existing pair of jeans into this fashion-forward style, all with a simple fold.

Still, there are so many vintage-inspired shapes to choose from. Better yet, the market is currently saturated with modern versions of these archival styles, meaning that you don’t have to go hunting down Brick Lane’s boutiques for a pair of old school Levi’s to fill this gap. Below, Who What Wear rounds up the 5 key ‘90s jeans trends that are spearheading spring 2026, the styling differences between now and then and the best updated pieces to shop.

5 90s Jeans Trends Spring 2026

1. Bootcut Jeans

Style Notes: Despite originating in the rodeo, these days, you’re more likely to find bootcut jeans in high-end restaurants. With a soft flare and extra sumptuous to the touch, this silhouette benefits from its ability to be dressed up and down with aplomb. Complementary to longline coats, cropped jackets, knitted sweaters and even humble white t-shirts alike, the sleek widening effect will help any outfit appear both considered and casual.

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2. Mid-Rise Jeans

Style Notes: If the ‘00s had low-rise, almost-bumster-level jeans and the ‘10s had ultra high-rises that rode up to the bottom of your ribcage, then both the ‘90s and now have mid-rise shapes. Consider this like the Goldilocks of jeans—a placid, low-effort and easy-going style that serves as a happy medium between both these extremes. In fact, you’ll find that the most sought-after denim styles of this decade are actually mid-rises, including Khaite’s beloved Danielle jeans and Agolde’s ‘90s pinch waist style. (How very apt!)

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3. Dark Wash Jeans

Style Notes: When it comes to ‘90s jeans trends, you must remember that it’s not always about the specific cut. Indeed, sometimes it comes down to the colour you wear. And if you were to flick through shots of memorable outfits from the period, you’ll often find tastemakers of the time gravitating towards dark washes. From deep blues to saturated indigos, the rich-looking hue can’t help but look far more premium than its lighter counterparts, leading to the wearer coming across as more thoughtful and chic.

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4. Stovepipe Jeans

Style Notes: If there’s one denim trend that will continue to dominate, it’s stovepipe jeans. A successor to the cigarette jeans that defined the early part of the decade, this style sits a little more loosely through the thigh and finishes with a punctuated and polished clean-cut hem. Style with mock croc court shoes, simple slingbacks or even a simple ballet flat. Regardless of the choice, the stovepipe shape will suit anything it’s styled with.

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5. Cuffed Jeans

Style Notes: From Lila Moss to Emily Ratajkowski and Michaela Coel, the most refined dressers of this day and age have taken to intentionally cuffing their jeans. Though this was a technique embraced by Jennifer Aniston all those years ago, the effect remains the same, leading to an outfit brimming with visual contrast, thanks to the barely-there two-toned effect.

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Working in fashion means that sartorial inspiration can strike at any notice. This could come in the form of subconsciously soaking up the outfits of your fellow passengers on your commute to work before realising you’re replicating them the next time you're in the office or simply lusting over something you’ve seen on your daily social media scroll. The latter happened to me the other day, when I inadvertently stumbled upon a photo of Cindy Crawford visiting Kaia Gerber on the set of Ryan Murphy’s new ‘80s thriller, The Shards.

Now, I’m not immune to the lure of the iconic off-duty images of Cindy during her ‘90s heyday. There’s something about the effortlessly polished, girl-next-door ease that always pulls me in and wishing for a pair of perfectly taut vintage jeans or an expertly crisp white t-shirt. However, I’d be lying if I said I wasn’t more interested in the personal style of her daughter in all its sleek, slouchily romantic glory. That was until, as I mentioned, coming across this photo of the style muse’s timeless jeans outfit.

The look itself came a few weeks after the supermodel’s 60th birthday, further cementing why I gravitated towards it in the first place, which is that, when it comes to a great outfit, timelessness always wins out over trends. Wearing a pair of bootcut jeans, a satin button-down and a simple leather jacket—a formula she’s been relying on for four decades in a row now—the ensemble proved that investing in classic wardrobe staples that are insusceptible to the passage of time is the best choice one can make.

Indeed, Cindy has been stepping out in similar pieces for years, highlighting that even the upper echelons of fashion are quite strict in sticking to their self-imposed uniform. I might be from a different generation, but there is a lesson to be gleaned in knowing oneself and sticking to the garments that pique my interest.

Of course, it would be remiss to say that I’m not slightly taken by the polish of her sophisticated blouse and the casual elegance of her outerwear, let alone her trademark brunette bombshell blowout, and I doubt I’m alone in that. So, whether you’re looking to emulate her style philosophy or just her style, scroll on for Cindy Crawford’s over-50s jeans outfit that has this mid-20s talking.

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They say a wedding dress is the most important piece of clothing a woman will ever wear. Well, where’s the beauty in that if the style you’ve chosen to walk down the aisle in is far too elegant for everyday settings? For an increasing number of brides, the styles they selected to tie the knot in aren’t floor-grazing or aisle-dragging. Instead, short wedding dresses offer something altogether quite contemporary and unconventional. Indeed, call this their ‘something new’ in the way they’ve bucked convention, but as more couples opt for ceremonies that cater to their own tastes rather than adhere to traditions, it’s unsurprising to see cropped hemlines come to the forefront.

This isn’t just a response to modernity, however. Whilst perpetual brat, Charli XCX, might’ve made the most prolific endorsement for short wedding dresses when she wore Vivienne Westwood’s Nova Cora off-shoulder mini, but it’s not just the Aperol Spritz-adoring pop star who has chosen the unexpected for their big day. In fact, short wedding dresses have a storied history of being worn by prolific women who weren’t afraid to blaze their own trail, whether that be Mia Farrow, Audrey Hepburn, Sharon Tate, Lily Allen or Cindy Crawford. The most famous short wedding dress, however, remains Yoko Ono, who wed John Lennon wearing a pleated thigh-baring dress at the British consulate office in Gibraltar.

These women weren’t dressing to meet expectations. They were dressing with intention, just for themselves,” explains Annelise Sealy, founder of London-based bridal boutique, The Fall. “Choosing a short dress signals that same mindset—fashion-forward, self-assured, and unafraid to stand apart.”

Speaking about the ascent of short wedding dresses, she explains that several factors have contributed to the rise of this style. (And no, I’m not just referring to the length.) “Modern brides are more empowered than ever to make choices that genuinely reflect who they are,” Sealy adds. “Marriage no longer feels like a rigid rite of passage; it’s a personal milestone, so the dress doesn’t need to follow a prescribed formula.”

“I think a short wedding dress carries an inherent sense of confidence,” acknowledging that they put the focus on the woman, not just the gown. “It's the opposite of the prescribed norm, whilst feeling fresh, intentional, and fun. It also offers freedom—both literally and stylistically—as it’s easier to move and enjoy the day without managing layers of fabric or a long train.”

This last point resonates with the way most brides are approaching their ceremonies, too. “Short wedding dresses reflect how weddings themselves have evolved—smaller guest lists, city ceremonies, destination celebrations, and multi-day events,” Sealy continues. “They suit that modern pace and versatility, and lean into a sense of individuality rather than excess.”

As for wearing one well? “It’s definitely all in the details and styling! Sheer layers instantly elevate a shorter length, or you can play with volume by adding a dramatic sleeve or detachable train. A veil, gloves, bold heels, or statement jewellery can transform a short dress into something unmistakably bridal while still feeling fashion forward.”

So, whether you’re seeking something to wear to your civil, a second look moment or are simply wanting to find ‘the one’ in a style that’s more cropped, scroll on to see a fashion writer’s edit of the best short wedding dresses of 2026.

The Best Short Wedding Dresses to Shop in 2026

Why Trust Us

At Who What Wear UK, fashion is our speciality. Our editors have years of industry experience, from reporting on seasonal fashion trends seen at international fashion weeks to working with some of the most recognisable names in fashion. Every item we recommend is carefully selected based on current trends, quality and real-world wearability.

We regularly try on pieces ourselves—everything from best-selling jeans to designer shoes—and speak to external experts and fashion insiders, staying closely connected to what our readers are searching for. Our advice is grounded in expertise, and each and every buy we feature has to meet our exceptional taste standards—so you can feel confident in every recommendation.

Dressing for the airport is a problem. There's a reason Who What Wear has an entire section dedicated to chic air travel. But for Cindy Crawford? It hasn't been tricky for her, historically. And I'm not in the least surprised by this. In particular, the supermodel's '90s airport style was simple, elegant, comfy, and—importantly—totally translatable to 2026 fashion, with frankly zero tweaks needed.

Though there was some variation to this rule, jeans in every wash imaginable were the legendary model's typical calling card at the airport. Admittedly, that's a bold move for sitting in a tight space for hours, but as long as you pick a pair with a little stretch in it, it's also absolutely workable, and obviously chicer than your beloved leggings. Based on five specific outfits Crawford wore to the airport in the '90s, I've put together a shopping list for your next trip that should make you feel like a model off-duty on your way to, like, Mauritius or Gstaad, or wherever it is that models hang out.

The key to making an all-black outfit not feel boring is to play with texture, a principle Cindy Crawford knows well. All it takes is a silk black shirt, a crisp black jean and a velvet or pony black shoe. So simple yet so smart.

This is a fantastic outfit, and not just because of Crawford's megawatt smile. All the cool girls know that a well-chosen pair of dark sunglasses chic-ifies any look at the airport and beyond. Not that this almost-all-black outfit with light-wash jeans needed any help to begin with.

Another flight, another pair of jeans. Here is Crawford demonstrating that black and brown actually do go together, looking fabulous in touches of leather and suede with a preppy weekender bag.

Deviating from her jeans-at-the-airport norm, Crawford opted for a gauzy floral skirt for a romantic touch. The rest of the outfit? Yep, all black, and still super chic.

I don't know why this outfit reminds me of J.Lo, but it does. A contrast sweater wrapped around your shoulders is always the easiest way to make an impact with your fashion without even trying, and white jeans look great year-round, no matter what the naysayers tell you.

It was the best of times (sleek minimalism, distinct sub-cultures and Karl Lagerfeld at Chanel), it was the worst of times (gaudy trainers, ultra-baggy denim and a lack of online stores). But either way you cut it, the ‘90s were a time of memorable fashion, at least that’s the case for iconic ‘90s winter outfits.

From the reign of supermodels on the runway to the rise of legendary film starlets gaining cultural cache both on and off the red carpet, this decade delivered so many moments to take stock of. Yet, in my personal and professional opinion, there’s no better season for these tropes to excel than in cold weather.

Those with taste always turn to the past for sartorial inspiration. It’s why you’ll always see Alexa Chung channel her inner Courtney Love in a minidress and leopard-print coat, or Lila Moss take cues from her mother’s archive in a silky slip, fur-trimmed jacket or cigarette trousers. Whilst there’s no shortage of looks to mine if you’re ever in need of exemplary displays of style, I’ve always found that cooler settings are where these ensembles shine.

Prolific dressers of the time period delivered a masterclass in how to combat the elements with aplomb, mixing fuzzy coats with thermal layers to showcase how keeping frostbite at bay can actually be a chic affair.

There’s, of course, Carolyn Basette-Kennedy roaming the streets of New York in vintage Prada and Calvin Klein. Or, the likes of Cindy Crawford, who made every outing all the more sophisticated in her commitment to pared-back but well-edited wardrobe staples. Even, on the other side of the country in Los Angeles, someone like Winona Ryder, who proved that tailoring never goes astray.

The best of all, however, is simply how timeless these looks are. Though nearly 30 years have passed since these iconic ‘90s winter outfits were worn, they haven’t been subjected to the way the passing of time can age things. Classic and contemporary in equal measures, these are silhouettes that will only increase in relevance the further that we get away from them. (You only need to see the fervour that surrounds Tom Ford’s collections for Gucci for evidence of this fact.)

But to me, these iconic ‘90s winter looks serve more as an antidote to the vicious hyper-accelerated trend cycle or constant regurgitation of niche aesthetics than anything else. Yes, triangle scarves and textured hats might be trending now, but to truly wear them well, you must look back at when these pieces originated. In fact, I’d even wager that these items are only relevant now because of the elegant It girls who wore them first.

At least, that’s the mood I’m channelling, with the impactful looks I’ve chronicled ahead, ones I’ve pegged to replicate over the next few months. So, without further ado, keep scrolling through for the 11 most iconic ‘90s winter outfits that will certainly influence your own, as they have mine.

But before we begin, test your knowledge of the most iconic '90s winter outfits with our short quiz, below.

The 11 Most Iconic '90s Winter Outfits

1. Gwyneth Paltrow

Style Notes: Gwyneth Paltrow has always been a beacon of discerning minimalism. Whilst her looks today lean more clean-cut with a coastal, Californian edge, the actress and wellness maven's sense of dress back in the '90s was fitting with the grit and industrial slant of New York, where she spent her teenage years. From charcoal-coloured sets to animal print coats, her wardrobe is a case for polish with an attitude.

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2. Carolyn Basette-Kennedy

Style Notes: Known mononymously as CBK, the late Calvin Klein publicist is a perennial enigma. She was exceptionally private, especially as her marriage to political scion John F. Kennedy Jr. brought her closer to the limelight, meaning the only glimpses at her personal life were through the clothes she armoured herself in. Thankfully, these were always equally remarkable, including an arsenal of Manolo Blahnik, Jean Paul Gaultier and Cartier.

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3. Winona Ryer

Style Notes: From Heathers to Hawkins, Winona Ryder has always been something of fashion's enfant terrible. As one of the original scream queens, the actress has never shied away from a darker sensibility made popular today by Gabriette or Jenna Ortega. Slightly gothic, slightly grungy, but always fitted and austere, her looks are the definition of haunting glamour.

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4. Cindy Crawford

Style Notes: Olivia Rodrigo might have herself pegged as this century's All-American girl, but if we were to look back to the '90s, it's Cindy Crawford who would've been crowned this title. Having grown up on the outskirts of Chicago, Crawford's proximity to fashion's elite in style capitals like Paris and Milan never strayed her from her inimitable penchant for effortless, breezy style. Her winter outfits demonstrate that considered cuts and thoughtful shapes will never falter.

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5. Sarah Jessica Parker

Style Notes: Whether on screen as Carrie Bradshaw or off-duty in her own right, Sarah Jessica Parker has always held her own. This textured coat is the exact thing you'd find in so many modern savant's wardrobes, including a up-cycled Conner Ives version, a leopard-print style from Queens of Archive and a rebelliously fringed iteration from East London-based brand Jakke.

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6. Jennifer Aniston

Style Notes: If you were to stroll through Primrose Hill on a Saturday morning or any Hackney cocktail bar on a Saturday evening, you'll be sure to find someone wearing something similar to what Jennifer Aniston wore here to the second annual Women in Film event in 1999. From the shearling-effect coat to the straight-leg trousers and square-toe boots, this is an outfit that's as easy to copy as it is to shop.

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7. Julia Roberts

Style Notes: Winter fashion isn't as fickle as other seasons tend to be. But, if there is one piece that will always endure, it's the grey coat. Here, whilst filming something in New York in 1999, Julia Roberts shows exactly why. Pairing it with her megawatt smile, chunky loafers and pleated trousers, the iconic look demonstrates that when it comes to battling cold weather, sometimes your coat can be your entire outfit.

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8. Halle Berry

Style Notes: A velvet shirt? Check. A boxy blazer? Tick. Leather boots that graze the knee? Yes, indeed. Halle Berry's '90s winter outfit isn't a far cry from something you'd find in suburbs like Greenwich Village or Le Marais today. Take notes from the Catwoman star and opt for sumptuous materials and evening-appropriate shapes.

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9. Princess Diana

Style Notes: Though Princess Diana famously spent the season in exclusive alpine villages throughout Austria, she still made her stomping ground of London a place to parade her iconic winter outfits. Here, she injects her frosty white base layer with a hint of royal prep as she heads to a day of shopping in Knightsbridge.

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10. Sofia Coppola

Style Notes: Before she was the auteur of soft and saccharine femininity with films like The Virgin Suicides and Marie Antoinette, Sofia Coppola was making a name for herself in the underground scenes with a short-lived television series she co-hosted with fellow Hollywood nepo baby Zoe Cassavetes called Hi Octane. This picture was taken of her during the show's run in 1994, epitomising her candid and dreamlike approach to fashion that would come to define her later work.

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11. Courteney Cox

Style Notes: Slouchy and carefree aren't the traits we attribute with Courteney Cox's iconic role as Monica Geller in Friends. But, it's this uncomplicated approach to style that's come to define her iconic off-duty style. Breathable and light, this outfit can be dressed up and down for the climate, just add a lightweight turtleneck and a leisurely V-neck jumper.

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Why Trust Us?

At Who What Wear UK, fashion is our speciality. Our editors have years of industry experience, from reporting on seasonal fashion trends seen at international fashion weeks to working with some of the most recognisable names in fashion. Every item we recommend is carefully selected based on current trends, quality and real-world wearability.

We regularly try on pieces ourselves—everything from best-selling jeans to designer shoes—and speak to external experts and fashion insiders, staying closely connected to what our readers are searching for. Our advice is grounded in expertise, and each and every buy we feature has to meet our exceptional taste standards—so you can feel confident in every recommendation.

Finding something different to wear every day of the week can be a challenge, but the good news is that there are a few foolproof outfits to wear when you're at a loss. I find myself digging through drawers and staring at the same items in my closet over and over again with that one thought we always have from time to time: I have nothing to wear. Luckily, Cindy Crawford is here to remind us of a jean outfit that has stood the test of time

While out to dinner in Beverly Hills recently, Crawford wore a leather jacket paired with jeans and brown boots. It sounds too good to be true, as it's so simple, but it’s an elegant outfit formula that will never fail you, no matter what the decade may be. Crawford would know, as she’s worn this exact outfit formula on repeat occasions since the '90s. What I love about this look is that it suits anyone with any type of style. It’s a versatile outfit that’s great for going out to dinners or meeting up with friends, and laid-back enough to give off an effortless vibe—true model-off-duty look.

If you’re on the market for a simple, but elegant outfit to wear over and over again like Crawford, keep scrolling to recreate her look and shop similar items.

In 2025

In 1991

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As a fashion editor, I'm always being asked about investments that will stand the test of time. As much fun as a viral product can be to incorporate into your usual rotation, nothing feels better than buying something that won't be considered "out" in a few months or even years. Case in point: leather motorcycle jackets. No matter their age, their personal style, or how long they've owned it, owners of moto jackets are never regretful about their purchase—not ever. It's one of those items you throw on again and again, but if you're feeling any doubt about buying one, listen up. To really hammer home how timeless leather motorcycle jackets are, look at Demi Moore, Cindy Crawford, and Amber Valletta, three women over the age of 50 with great style who have been wearing leather jackets for years and still wear them regularly. The style has become a staple in their wardrobes, and it probably always will be.

I most recently spotted Moore wearing an oversize version with her dog Pilaf in New York City. With it, she wore a sheer lace maxi skirt as well as a button-down shirt, knee-high boots, and Brandon Maxwell's viral newspaper kiss-lock bag from its S/S 26 show in September. The handbag shape and lace detailing on her skirt are both quite elegant, but her choice of a leather jacket and all-black color palette gave the look some edge, making it feel right at home in Manhattan.

On Demi Moore: Brandon Maxwell The Maxwell Bag ($2200)

During Paris Fashion Week at the end of September, Valletta attended the Saint Laurent S/S 26 show alongside a bevy of other friends of the house, including Hailey Bieber and Zoë Kravitz. For the occasion, the supermodel donned her Saint Laurent leather jacket—a mix between a motorcycle style and a bomber—with nothing underneath, adding a high-low black miniskirt, sheer tights, and patent-leather pumps. To double down on the '80s theme, she wore two silver cuff bracelets. Kate Moss also wore a similar leather jacket in Paris during fashion week, though she styled hers with lace-trim shorts and fishnets.

On Amber Valletta: Saint Laurent jacket, skirt, bracelets, and shoes

Finally, in the spring, Crawford was photographed in a leather motorcycle jacket, but she was in California, not New York or Paris, proving just how versatile this outerwear silhouette is. She was stepping out of dinner with Kate Hudson at Giorgio Baldi in Santa Monica, wearing a cropped version of the jacket style with a black T-shirt and a matching midi skirt with a high slit. She finished off the effortless, off-duty ensemble with black tall boots and a matching shoulder bag.

Clearly, a black leather motorcycle jacket works for every occasion, in every city, and with every outfit, though it's best suited with skirts, black ones in particular. There's just an easy elegance that comes with black skirts and leather jackets. You don't have to question it—the pairing just works.

Scroll down to find your forever leather motorcycle jacket.

Shop Leather Motorcycle Jackets

The celebrity-approved way to wear flared jeans isn't grounded. It's elevated. No one demonstrates this better than OG supermodel Cindy Crawford. The 5'10" style star is constantly spotted in the long, leg-lengthening denim silhouette, and here's the kicker: She almost exclusively pairs it with heels.

Crawford often leans into the elevated aesthetic by opting for sleek black pumps, pointed-toe heeled boots, and even sophisticated high-heeled sandals, depending on the occasion. When combined with a little extra height, the flare of the jeans elongates the leg, ensuring the outfit says, "I'm off the clock, but I still have a reservation."

Take a page from the '90s icon's playbook and leave the flats for your leggings. Whether you choose dark-wash wide-leg jeans or true '70s-style flares, the key to unlocking their full potential is shoes with a couple of extra inches. Find classic stacked pumps or sleek leather booties that peek out under the hem, and you'll have your new favorite, most flattering denim outfit formula. Keep scrolling to browse jeans, shoes, shirts, and accessories that can be mixed and matched to re-create Crawford's look.

Re-Create Cindy Crawford Casual Denim Outfit

Nineties fashion hits different in the fall—it's a master class in textured suede fabrics, funky animal prints, light-wash denim, and all-black turtlenecks. Think Julia Roberts at LAX in her oversize blazer and light-wash jeans or Courteney Cox at a Hollywood premiere in a simple white button-down and slim trousers. The ultimate goal of '90s fall fashion was to achieve a casual elegance.

Every day, I wake up, look at my closet, and wonder how I can achieve that effortlessly cool '90s celebrity fall fashion look. I'm talking Jennifer Aniston, Halle Berry, Iman, Cindy Crawford, Elle Macpherson… The list goes on. Minimalism and clean lines defined the decade, with not a logo in sight, just elevated basics styled to look rich. That's precisely why each one feels so timeless and easy to replicate because chances are you already own a similar piece.

I can't get these 10 '90s celebrity fall fashion looks out of my head, so I've decided to re-create them with modern finds from Nordstrom (my go-to for all my fall shopping). Scroll down to discover the timeless '90s inspiration and how to wear it this fall.

10 '90s Fall Outfits to Re-Create This Season

Jennifer Aniston

Style Notes: '90s icon Jennifer Aniston is spotted in a blue miniskirt, black turtleneck and a long black overcoat.

Halle Berry

Style Notes: Actress Halle Berry wears an animal-print coat with a pair of light-wash denim and a velvet turtleneck.

Elle Macpherson

Style Notes: Australian model Elle Macpherson was potted at LAX in 1997 in a belted brown jacket, a classic black turtleneck, and kick-flare trousers. She grounds the look with a timeless pair of loafers.

Courteney Cox

Style Notes: Friends star Courteney Cox casually ties her sweater around her waist at a Hollywood premiere.

Tyra Banks

Style Notes: Tyra Banks wears a Canadian tuxedo paired with black leather Western boots and a backward cap.

Gwyneth Paltrow

Style Notes: Gwyneth Paltrow poses in a pair of leather pants and a fitted black turtleneck.

Kate Moss

Style Notes: Posing in a Saks Fifth Avenue store, supermodel Kate Moss sports a '60s silhouette. Her white miniskirt contrasts with her elegant black crewneck long-sleeve and pointed-toe ballet flat.

Iman

Style Notes: Iman wears an all-white ensemble at a premiere in NYC. The turtleneck underneath the ivory blazer elongates the chic look.

Cindy Crawford

Style Notes: Model Cindy Crawford arrived at LAX in 1991 sporting a leather blazer, straight-leg jeans, and a fitted black turtleneck.

Julia Roberts

Style Notes: Julia Roberts spotted at LAX in a very '90s 'fit. The oversize blazer complements the relaxed fit of the jeans.

Some of the top fashion moments of the 78th annual Cannes Film Festival include Bella Hadid wearing over 100 carats of Chopard emeralds and Irina Shayk in polka-dot Armani Privé. That said, the red carpet is only the tip of the iceberg. Celebrities tend to wear more laid-back looks for daytime events scattered around the city. One standout outfit? Alessandra Ambrosio's white jeans.

The very same day that Ambrosio took a stroll around Cannes wearing white flare jeans, Cindy Crawford was photographed over 6000 miles away wearing similar pants. In Beverly Hills, Crawford wore white jeans that were also full-length but featured a baggier and more wide-leg silhouette compared to Ambrosio's choice. Both options are fantastic if you want to wear white jeans in summer—there's truly no wrong answer. Scroll down to see how Alessandra Ambrosio and Cindy Crawford wore white jeans in different corners of the world.

Alessandra Ambrosio's Flared Jeans in Cannes

On Alessandra Ambrosio: Veronica Beard Beverly Skinny-Flare Jeans ($248); Lounge Tallulah Intimates Set ($110)

Cindy Crawford's Wide-Leg Jeans in Beverly Hills

This post was published at an earlier date and has since been updated.

It may surprise you, but women in their 20s and 50s share similar fashion choices, especially when it comes to color trends. How do I know? Well, 23-year-old Kaia Gerber and 58-year-old Cindy Crawford were recently spotted in navy outfits.

For Gerber's debut performance in Evanston Salt Costs Climbing in L.A. over the weekend, the mother-daughter duo was photographed in semi-matching ensembles. Gerber wore a navy T-shirt and flowy navy pants paired with a distressed brown leather jacket, while Crawford opted for wide-leg blue jeans, a navy sweater, and a coordinating blazer.

On Kaia Gerber: Veda Marco Leather Oversized Bomber ($658); Paloma Wool Philana Bag ($395); Repetto Camille Rubber Sole Ballet Flats ($324); Library Science hat

It's interesting to see how navy is gradually becoming the new go-to neutral, quietly replacing black as the versatile dark hue of choice. Although navy has always had a place in fashion, it is now emerging as a modern alternative to traditional black staples in our wardrobes. It's not just Gerber and Crawford making the case for this color trend; celebrities like Kate Hudson and Justine Lupe have also recently embraced the hue, wearing navy gowns at the 2025 Golden Globes.

Whether you're in your 20s or 50s, one thing is clear: Navy is the new black, and with style icons like Crawford and Gerber leading the way, we can expect to see more women turning to this timeless yet fresh shade.

Shop the best navy pieces:

Every fashion person knows that sometimes there's nothing more expensive looking than wearing white jeans—even during the winter. This sentiment has recently been echoed by stylish celebrities like model Cindy Crawford and fashion maven Alexa Chung, who were both recently seen donning white jeans styled similarly.

Just last week, Crawford took to Instagram to unveil a casual pre-Christmas outfit. She paired a cozy tan sweater with a vibrant printed scarf that added a splash of color. On the bottom was a pair of crisp-white straight-leg jeans and tan suede loafers, blending comfort with style in a perfectly effortless way. Similarly, Chung was spotted yesterday walking the streets of London in a long army-green Barbour jacket that melded functionality with flair. Her impeccably tailored white jeans provided a clean contrast to her outerwear. Just like Crawford, Chung completed her outfit with loafers.

While pointed-toe ankle boots and suede sneakers have also gained traction this season as popular choices for styling white jeans, loafers have firmly established themselves as a wardrobe staple. They have become a beloved choice for fashion enthusiasts from L.A. to London and beyond year-round because the combination offers endless styling possibilities—as demonstrated by Crawford's choice of tan suede and Chung's sophisticated black leather—no matter the occasion or climate.

On Alexa Chung: Barbour jacket

As the outfit formula will certainly continue its dominance well beyond winter and into spring next year, read on to discover our edit of the best white jeans and loafers to shop now.

Shop our favorite white jeans and loafers:

On Saturday night, the most stylish members of Hollywood's elite met up in Los Angeles for the Academy Museum Gala, otherwise known as the "West Coast Met Gala." Kendall Jenner wore Schiaparelli couture, Ayo Edebiri wore Thom Browne couture, and Laura Harrier wore Ludovic de Saint Sernin. And those were just some of the highlights. Another sartorial masterclass was taught by Kaia Gerber, who attended the event wearing archival Givenchy by Alexander McQueen from the designer's fall 1997 couture collection. Following the gala, the model kept up the good work, attending an after-party at Chateau Marmont in an LBD that could have easily been snatched from her mom, Cindy Crawford's '90s wardrobe.

Almost exactly 30 years earlier, Crawford attended the 5th annual Fire and Ice Ball, a benefit for Revlon UCLA Women's Cancer Center, in Century City on December 7, 1994. Like her daughter, the supermodel often leaned on timeless colors and silhouettes, rarely falling under the spell of trends, so it should come as no huge surprise that, for the benefit, she chose a sleeveless black dress with a sweetheart neckline not unlike the one Gerber chose this weekend. She styled it with a matching shawl, a diamond cross-pendant necklace, and a tennis bracelet.

Like her mom, Gerber kept her after-party ensemble simple and timeless by wearing strappy black sandals, a black satin Judith Leiber clutch, and the same RW Fine Jewelry choker that adorned her neck at the earlier gala.

Scroll down to see Gerber's 2024 interpretation of her mom's go-to night-out look from three decades ago.

On Kaia Gerber: Judith Leiber Couture Gemma Crystal Satin Clutch Bag ($995)

Shop the Perfect $70 Alt for Kaia's LBD

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If you could peek inside any fashion editor's shopping basket right now, you'd likely spot a common theme unfolding. Among a plethora of white T-shirts and tank tops, there's a new summer shoe trend that's circulating stylish groups and working its way into the wardrobes of so many prolific dressers.

Worn most recently by Kaia Gerber, the heeled flip-flops trend is emerging as the breakthrough shoe of the season. Featuring a small heel and a sleek strappy finish, the shoe style draws the line between smart and casual, offering a fresh summery footwear solution that fashion people have come to adore.

Styling hers with a black minidress, Gerber's look channeled a '90s energy that compliments the shoe trend so well. Accessorizing with a sleek shoulder bag and black sunglasses, the model's look felt aptly chic for the Parisian setting.

Enjoying a mother-daughter day out, Cindy Crawford was also spotted in Paris with Gerber. For their outing, the supermodel selected a pair of anti-trend white sneakers to complete her relaxed ensemble. Avoiding flashy colors and new-season silhouettes, Crawford's choice worked perfectly with her relaxed jumpsuit outfit while providing her with the comfort needed to stroll around the French capital.

Between Gerber's new-season yet potentially timeless-looking micro heels and Crawford's classic kicks, there's no denying that the two possess an eye for excellent shoes. To shop the styles I'm sure would come with both models' stamps of approval, read on to discover our edit of the best heeled flip-flops and white sneakers below.

SHOP OUR EDIT OF THE BEST HEELED FLIP-FLOPS

SHOP OUR EDIT OF THE BEST WHITE SNEAKERS

This post originally appeared on Who What Wear UK.

If you could peek inside any fashion editor's shopping basket right now, you're likely to spot a common theme unfolding. Amongst a top-up of white T-shirts and a tank tops, there's a new summer shoe trend that's circulating stylish groups and working it's way into the wardrobes of so many prolific dressers.

Worn most recently by Kaia Gerber, the heeled flip flop trend is emerging as the breakthrough shoe of the season. Featuring a small heel and a sleek strappy finish, the shoe toes the line between smart and casual, offering a fresh summery footwear solution that fashion people have come to adore.

Styling hers with a black mini shift dress, Gerber's look channeled a '90s energy that compliments the shoe trend so well. Accessorising with a sleek shoulder bag and black sunglasses, the model's look felt aptly chic for the Parisian setting.

Enjoying a mother-daughter day out, Cindy Crawford was also spotted in Paris with Gerber. For their outing, the supermodel selected a pair of anti-trend white trainers to complete her relaxed ensemble. Skirting flashy colours and new-season silhouettes, Crawford's choice worked perfectly with her relaxed jumpsuit outfit, whilst providing her with the comfort needed to stroll around the French capital.

Between Gerber's new-season yet potentially timeless-looking micro heels and Crawford's classic kicks, there's no denying that the two possess an eye for excellent shoes. To shop the styles I'm sure would come with both models' stamps of approval, read on to discover our edit of the best heeled flip flops and white trainers below.

SHOP OUR EDIT OF THE BEST HEELED FLIP FLOPS:

SHOP OUR EDIT OF THE BEST WHITE TRAINERS:

Say hello to Unfiltered, a fresh beauty series where you'll get an exclusive glimpse into the dressed-down beauty routines of our favorite celebrities and content creators. They'll reveal their guilty-pleasure beauty practices, the five-minute-routine product lineup they can't live without, the one good-skin tip they'll be forever thankful for, and so much more. To bring every conversation full circle, we ask each celebrity to send us a selection of self-shot, filter-free photos of their choosing to capture the essence of their Unfiltered beauty philosophy.

Up next, we're getting to know supermodel Cindy Crawford, the founder of Meaningful Beauty. Below, she's answering all of our rapid-fire questions and sharing her favorite products, best-kept beauty secrets, and more. Enjoy!

Congratulations on 20 years of Meaningful Beauty! Are there any lessons you've taken from your expansive career as a model and channeled into Meaningful Beauty?

Thank you! During most of my time working as a model, I wasn't doing my own makeup. My job was to show up with clean hair, nails, and skin. That's how I got passionate about skincare. In terms of being the founder of a beauty brand, I think what I learned from being around so many creatives is authenticity. I've seen again and again that what works best for a brand is a real story, vision, and mission. You can't fake that stuff—especially now—because there's so much direct interaction with your consumer.

As a model and beauty founder, could you share a few beauty tips and tricks you swear by?

The best beauty trick is having a makeup artist! But if you can't have a makeup artist, young women today who want to learn how to do makeup have incredible online tutorials they can use. If my daughter wants to try something new with her makeup, she just goes on YouTube and learns it. My generation didn't have that. For me, one of the things I learned from makeup experts is to make sure you have a good foundation and make sure it matches.

Another beauty secret I've learned as I've gotten older is that too much powder actually ages you because it settles in your creases. Also, don't be afraid to experiment with your look! I'm speaking more to my age group, but it's easy to get stuck in what was cool when you were 25. Go get a makeup lesson at a beauty counter and try something new so you don't look dated! You can do the same thing for your makeup, hair, and approach to styling.

I always think it's funny how past beauty trends make the rounds and influence younger generations. In fact, I've been seeing looks inspired by the 1992 Pepsi commercial you starred in floating around recently.

Oh, definitely! That entire look was timeless. The white tank top and pair of cutoffs I was wearing 32 years ago will never go out of style.

The full brows and big hair you wore for that shoot have also been on the rise lately! Are there any products you've been loving lately that you have with you when you're on the go?

Well, obviously, I love Meaningful Beauty, and it's always my go-to when it comes to skincare. I'm a big fan of dry-brushing for the body. I'm really obsessed with tongue scraping, which I travel with, and using the Dyson Airwrap because it makes it easy for me to do my own hair since it gives the tension I need with the brush and blow-dryer combined.

I don't really wear a lot of makeup when I'm not working, so I love a perfect lip gloss that looks like the perfect bitten lip, like Tarte's Maracuja Juicy Lip Plump in their black cherry shade. There are also old classics I always come back to, like an Armani Beauty Luminous Silk Natural Glow Foundation. I like to mix it with their Luminous Silk Hydrating Makeup Primer because I like my foundation sheered out a little bit for real-life wear with light coverage.

I'd love to hear more about Meaningful Beauty. What inspired you to dive into the skincare world and launch the brand 20 years ago?

At the time of the launch, I had been with Revlon for 15 years. My contract was up for renewal, and I was 35. Two things happened: First, I've always been passionate about skincare and felt that my job as a model was to show up as a model with great-looking skin. For me, it was less about the cosmetics and more about the actual skincare. Plus, I was 35 and was like, "Oh shit, my skin is going to age, too, like everyone else's!" I had also met [Jean-Louis Sebagh, MD] in Paris when I was 28.

He's the one who really showed me what good skincare could do. Before that, I don't think I believed that there were really efficacious ingredients you could use on your skin that would actually make it look better. I understood the importance of a good, basic skincare routine like using moisturizer, but I didn't know the science. It was the early days when science was really getting into skincare, and we were starting to see the results of retinol and other ingredients like that.

I had this passion for skincare, met the right partner, and was at a time in my life when I decided to do my own thing, and that's how Meaningful Beauty was created! It's called Meaningful Beauty because we wanted to create products that are meaningful. The name just kind of stuck.

It's such a catchy name! Can you share what you wanted the biggest takeaway to be for consumers? What was the goal?

I grew up in the Midwest with a mom and two sisters. We weren't raised reading fashion and beauty magazines, so when I got exposed to all that through my job as a model, I wondered how I could share what I had learned with women everywhere in a way that's affordable, easy to use, and will always get great results. It was about bringing Dr. Sebagh's expertise to my sister, my mom, and friends.

How has creating your own beauty brand influenced your perception of beauty?

To me, what's meaningful about beauty is the confidence women can have when they feel good about themselves. Think about what it's like when you have nice hair and a cute top, and you have that little "I got it going on today" feeling. When you look good, you can go through your life with confidence. My whole thing about the beauty line is less about achieving beauty and more about what happens when women feel beautiful. We're not about starting trends. We just want to offer effective products to women that can be used daily. Skincare is a commitment. If you do it every day and you're nice to it, it'll be nice to you.

What do you see being the brand's next chapter? What about 20 years down the line?

I don't know about another 20 years from now since I don't think that far ahead. Of course, we're always innovating. What's been really exciting this year and what I imagine will be going forward is tapping into our customers more. We just hosted a party in L.A. that we filmed with about 40 women who have been customers. Some have been customers since the very beginning! They are the best people to speak on the brand since they've committed to it for 20 years.

Moving forward, we want to listen to them even more and ask where we don't have them covered. Should we be adding more haircare? What about bodycare? It will be about meeting women where they are and giving them what they want. We also want to bring their voices more into the brand message. It's not a vanity project, and I want it to have a life beyond me. Meaningful Beauty is about creating meaningful products but also touching on what's meaningful about beauty. I know we have some innovation coming with our day cream. We're looking to add a device! We're trying to give women more tools and confidence.

If someone wanted to follow in your footsteps—whether it's modeling, starting a skincare brand, or both—what advice would you give them?

There's a lot more diversity in modeling than when I entered the industry, and a lot of it is luck of the genes. Developing a personal brand and knowing who you are or what values you stand for is where you should start. Start with, Who am I, and what do I believe in? If you wanted to start a brand, you should ask if it's organic and authentic to you [and] if you're proud to put your name and face on it. I've always tried to use that as a test for every choice I make, especially professionally, to judge if something feels right.

Finally, what is your Unfiltered beauty philosophy?

Fake it 'til you make it! Also not being terrified of aging. Understand that it's not always a piece of cake but accepting it and focusing on the good stuff.

Shop Cindy Crawford's Unfiltered Beauty Edit

As far as mother-daughter duos go, few others can claim such a great influence over the fashion industry as Cindy Crawford and Kaia Gerber. With cumulative decades worth of time in the industry, the pair have both fronted some of the biggest campaigns out there. Having spent so much time in fashion's inner circle, it's no surprise that the two have honed excellent taste along the way.

With 36 years between them, what is surprising, however, is just how similar their style preferences are. Attending an event in Paris over the weekend, both models opted to wear the same ageless item, selecting chic black dresses for the evening occasion they attended together.

With subtle differences that spoke to their tastes, Gerber chose her strappy LBD in a shorter length with an elegant sweetheart neckline. Pairing her black dress with burgundy Gucci slingback shoes, the model kept her outfit minimal and sleek, selecting only a few simple jewels and an elegant watch to complete her look.

Also choosing a sleeveless black dress, Crawford's iteration fell below her knees and included a sophisticated cowl neckline. Accessorizing with The Row's Mel clutch bag ($1450) and a pair of strappy sandals, the supermodel also kept her jewelry to a minimum, selecting a single paper chain necklace and small gold hoops.

With access to endless designer options and countless new-season buys, the duo's choice speaks to the enduring appeal of a little black dress. Versatile, flattering and so easy style, the classic buy is a wardrobe staple for a reason.

Read on to shop both Kaia Gerber and Cindy Crawford's black dress outfits, as well as discover our edit of the best black dresses on the market.

SHOP KAIA GERBER'S LOOK

SHOP CINDY CRAWFORD'S LOOK

SHOP OUR EDIT OF THE BEST BLACK DRESSES

This post originally appeared on Who What Wear UK.

As far as mother-daughter duos go, few others can claim such great influence over the fashion industry as Cindy Crawford and Kaia Gerber. With cumulative decades in the industry, both have fronted some of the biggest campaigns out there, and having spent so much time in fashion's inner circle, it's no surprise that the two have honed excellent taste along the way.

However, with a 36-year age gap between them, what is surprising is just how similar their style preferences are. Attending an event in Paris over the weekend, both models opted to wear the same ageless item, selecting chic black dresses for the evening occasion they attended together.

With subtle differences that spoke to their individual tastes, Gerber chose her strappy LBD in a shorter length with an elegant sweetheart neckline. Pairing her black dress with burgundy Gucci slingback shoes, the model kept her outfit minimal and sleek, selecting only a few simple jewels and an elegant watch to complete the look.

Also choosing a sleeveless black dress, Crawford's iteration fell below her knees and included a sophisticated cowl neckline. Accessorising with The Row's Mel Polished Leather Clutch (£1350) and a pair of strappy sandals, Gerber's mother also kept her jewellery to a minimum with a single paper chain necklace and small, gold hoops. With access to endless designer options and countless new-season buys, the fact that they both chose a little black dress speaks to the enduring appeal of this timeless classic. Versatile, flattering and so easy to style, it's a wardrobe staple for a reason.

Read on to shop Kaia Gerber's and Cindy Crawford's black dress outfits, and discover our edit of the best black dresses on the market right now.

SHOP KAIA GERBER'S LOOK:

SHOP CINDY CRAWFORD'S LOOK:

SHOP OUR EDIT OF THE BEST BLACK DRESSES:

I think we can all agree that supermodel and Malibu resident Cindy Crawford is the ultimate classic California girl. She's perfected that breezy, effortless style that looks as relevant today as it did in 1994. Trends come and go, but Crawford's timeless wardrobe is forever. So it goes without saying that she's a great person to look to if you want to see what people actually wear in L.A. day-to-day.

I no longer live in L.A., but I visit at least annually, and every time I do, I see people wearing a specific jeans-and-sandals pairing: white jeans and flip-flops. This summer-friendly combination is chic and polished and even a bit trendy now that white jeans and flip-flops are so popular among the fashion crowd. That said, they're never really not trends, so you can feel good about your decision to purchase and wear them no matter where you live. Keep scrolling to do just that.

Shop White Jeans

Shop Flip-Flops

Aside from the whole supermodel thing, Cindy Crawford is actually extremely relatable—well, at least her latest choice of footwear is. Photographed in Malibu, Crawford wore a chill denim outfit with a pair of Birkenstock Madrid Big Buckle Slide Sandals ($140). The classic shoes have nearly 200 five-star reviews on Nordstrom's website, with many shoppers saying they own them in multiple colors. Other reviews mention how they're the perfect mix of comfort and style.

Dare I say these are the most versatile shoes of summer? The slides can be styled in a million ways. They'll look equally chic on your next beach trip, countryside excursion, or city escape. I'll personally be styling them with a floaty printed midi dress and a raffia tote bag for my upcoming travels in June and July. Scroll down to see Cindy Crawford's newest outfit, and shop her exact sandals.

On Cindy Crawford: Birkenstock Madrid Big Buckle Slide Sandals ($140)

Shop Cindy Crawford's Exact Birkenstock Sandals

Shop More Birkenstocks

Cindy Crawford has been on our fashion inspiration board since the '90s, so it's no surprise that the 57-year-old icon is still a style star, even—or perhaps especially—while off duty. 

Crawford was recently spotted wearing a familiar favorite Breton-striped quarter-zip sweater, super-dark denim, and simple Horsebit loafers while out and about in Los Angeles. Whether you call it model-off-duty, quiet luxury, or French-girl style, it all comes down to the same thing: curating an excellent set of wardrobe basics that can be worn and reworn endlessly. 

Take a cue from Crawford and shop sweaters, jeans, and loafers to create your version of the outfit. Accessorize simply with a gold chain necklace, a black tote bag, and, of course, supermodel-worthy sunglasses. With an outfit this classic, you're bound to turn heads everywhere from Pasadena to Paris. 

On Cindy Crawford: Gucci shoes

Re-Create Cindy Crawford's Jeans-and-Flats Outfit

When it comes to her denim choices, Cindy Crawford has been remarkably consistent over the past 20 years. Trends have come and gone at a rapid pace over the last two decades, but Crawford has remained loyal to one style in particular: boot-cut jeans. 

This week, Crawford was photographed wearing her go-to outfit: a white blazer and dark-wash boot-cut jeans. In fact, a bit of photo research led me to two other examples of her wearing the exact same combo, one back in 2004 and one in 2015. If this doesn't prove that this outfit combination is timeless, I don't know what will. Scroll down to see how Cindy Crawford styled boot-cut jeans across three different decades. 

Shop White Blazers and Boot-Cut Jeans

Versace has had a busy week. First, the brand showed its S/S 24 collection in Milan, featuring the likes of Claudia Schiffer, Natalia Bryant, Kendall Jenner, and Gigi Hadid on the runway. Next, the brand decamped to New York City for its inaugural Versace Icons dinner hosted by Anne Hathaway. And finally, Versace sponsored last night's Albie Awards hosted by Amal and George Clooney. Phew! I can hardly keep up.

At the Versace Icons dinner, Cindy Crawford's outfit immediately stuck out to me. She made jeans look exceptionally chic for a night out—are you taking notes yet? Specifically, she wore wide-leg jeans, which have been much more popular than skinnies with celebrities lately. Scroll down to see her new outfit and re-create it for yourself. 

On Cindy Crawford: Versace Mini Embellished Croc-Effect Leather Tote ($2195)

Re-Create the Look With 4 Key Pieces

1. Leather Blazer

2. Wide-Leg Jeans

3. Black Pumps

4. Top-Handle Bag

While every decade has had its fair share of iconic looks at the MTV Video Music Awards, the '90s take the cake in my opinion. When else could you see Pamela Anderson in a gigantic pink hat, Destiny's Child in matching sherbert-hued looks, and Gwen Stefani in a furry bra? 

Below, I rounded up my favorite '90s looks in VMAs history. Here's a hint of what to expect: The Spice Girls in their prime, Madonna in an elaborate costume for a performance, Jennifer Lopez in a sparkly top, and Cindy Crawford in a thoroughly modern outfit that could have been worn yesterday. Scroll down to revisit the most iconic looks from the MTV VMAs ahead of the 2025 event, which will be held on Sunday, September 7, in New York City.

When it comes to style inspiration from celebrities, you can rest assured that you're in good hands with supermodels. The supermodels I'm referring to in this case are Cindy Crawford and Kate Moss, two of the most eternally chic women on the planet. Coincidentally, both women stepped out in similar looks from opposite sides of the pond this week, and they answered an important style question you may have: What are the best jeans to wear with ballet flats?

According to both Crawford and Moss, the answer is cropped straight-leg jeans. Crawford wore her pointed-toe ballet flats with cropped white jeans and a lightweight button-down blouse, and Moss wore her traditional black ballet flats with cuffed jeans and a leather jacket. It makes perfect sense that they'd opt for cropped jeans, as ballet flats have very thin soles, and long, baggy jeans tend to swallow them up. You'd be wise to follow the OG supermodels' lead. Scroll to do so by shopping for cropped jeans and ballet flats that I highly recommend.

Shop Cropped Jeans

Shop Ballet Flats

For Kaia Gerber and Cindy Crawford, it's not just good looks that run in the family. The mother-daughter duo also share an innate sense of style, earning them top spots on countless best-dressed lists. Despite their 35-year age difference, Kaia and Cindy dress quite similarly and consistently rely on a handful of the same essential wardrobe staples.

Below, I rounded up four ageless trends that Gerber and Crawford both wear. Don't get me wrong. They don't always style these pieces in the same way. Each puts a unique spin on basics such as trench coats and striped sweaters. Scroll down to shop four trends inspired by fashion's chicest duo. 

1. Tan Trench Coat

Crawford prefers to wear a classic trench coat, while daughter Gerber is partial to an oversize version. Whichever style you choose, you're bound to look chic. 

2. White Jeans

White jeans are a perennial favorite this time of year. Copy Crawford and wear them with your favorite Birkenstocks or emulate Gerber and go with Converse sneakers. 

3. Collared Striped Sweater

Get yourself a collared striped sweater. You won't regret it. The French staple is a year-round favorite of both Gerber and Crawford. 

4. Bootcut Jeans

The styling options are limitless when it comes to bootcut jeans. Dress them up for a night out or pair them with a simple tee for running errands. 

Next, these 3 watches will never go out of style—I promise. 

As a muse to some of fashion's most legendary designers and photographers, Cindy Crawford no doubt has every luxury brand on speed dial. But when she's not walking a runway or red carpet, Crawford's style is more relatable than you might think. Case in point? She just wore a low-key outfit while grocery shopping in Malibu.

Crawford wore the Birkenstock Madrid Big Buckle Slide Sandals ($140) with white jeans and a basic crew-neck sweater, resulting in an easy-to-copy outfit perfect for running errands. I particularly love that the Birkenstock sandals Crawford wore come in six colors and boast rave reviews on Nordstrom's website. Keep scrolling to see Crawford's casual outfit and shop her exact sandals. 

On Cindy Crawford: Birkenstock Madrid Big Buckle Slide Sandals ($140)

Shop Cindy's Exact Shoes in Six Colors

Shop More Birkenstock Sandals

Next, Princess Kate just wore the bag trend that feels so fresh for spring. 

Opening image: Getty Images

When it comes to airport style, I am all about outfits that are comfortable without sacrificing style, and your shoes are the key component for accomplishing this. Heels are a hard no in my book, as well as any other footwear that makes for a complicated run through the security line. This leaves flat shoes like loafers, ankle boots, sneakers and my all-time favourite: ballet flats. While ballet flats truly never go out of style, they are currently at the forefront of shoe trends at the moment.

I know I am not alone in this preference as evidenced by the many stylish celebrities that are spotted traveling in the timeless flat shoe style, whether it's a Mary Jane style or a studded pair. Besides the ease, they instantly elevate even the most basic of outfits. Just don’t forget to pack a pair of socks in your carry-on to save you from a grimy barefoot walk through security. Ahead, check out eight inspiring celebrity airport looks with ballet flats. Plus, shop some of the chicest options out there right now.

1. Elle Fanning in Satin and Leather Ballet Flats

Style Notes: Fanning has a sleek and chic look that's softened with a pair of pink satin ballet flats with leather details.

Shop the Look:

2. Ashley Olsen in Two-Tone Flats

Style Notes: Olsen is effortlessly chic in a camel coat, black jeans, and two-tone ballet flats. As one co-founder behind The Row, it's no surprise she knows how to style flats, especially when her brand's own versions always sell out.

3. Jasmine Tookes in Black Ballet Flats

Style Notes: Tookes understands that comfort is key for any flight. Try a matching knitted set for in-flight comfort, and an easy pair of ballet flats for a delicate touch. You can never go wrong with classic black.

4. Kate Bosworth in Neutral Ballet Flats

Style Notes: For an easy, polished feel, try this look from Bosworth—white button-down shirt, cropped jeans, and neutral ballet flats. Flats in subtler tones will go with everything you've packed.

5. Cindy Crawford in Animal Print Flats

Style Notes: This easy-breezy outfit idea from Crawford requires four pieces: a trench coat, white T-shirt, slim jeans, and snakeskin flats. There are plenty of other faux animal print options too if you like this maximalist spin on the shoes.

6. Elsa Hosk in Shiny Flats

Style Notes: Hosk gives a sleek pair of shiny black ballet flats the model treatment with a statement off-the-shoulder top. Whether you prefer patent leather or something subtler, shinier textures always feel like a statement.

7. Michelle Williams in Pointe-Inspired Flats

Style Notes: Williams took the word 'ballet' seriously when it came to her look. She completed her stylish travel outfit with pretty pink ballet flats that are reminiscent of those actually used out on the vinyl dance floor. Opt for square pointe-inspired picks or those with rounded softer edges.

8. Miranda Kerr in Metallic Flats

Style Notes: Kerr is all smiles in a vibrant printed top, slim black jeans, and shiny square-toed flats.

More Stylish Ballet Flats to Shop Now