While it's easy to assume that there's a line between your summer and fall wardrobes, the best dressed people know that the two can happily coexist for those in-between months of August and September—provided you know how to style the pieces together. Today, we're getting a master class in transitional dressing by none other Dua Lipa, whose most recent outfit consisting of a polka-dot halter dress from Réalisation and black knee-high boots is a great example of how chic people will be getting dressed next month.

Lipa was spotted heading into NYC's famed Electric Lady Studios for the zillionth time this week, prompting fans to speculate about a fourth studio album in the making. While most of us would think to pair a pretty polka-dot dress with ballet flats or flip-flops, the pop star's simple shoe swap is actually kind of genius because it can extend the shelf life of all your prettiest dresses into the fall. She opted for a classic pair of black leather knee-high boots, a style that keeps returning year after year.

Ahead, see how Dua Lipa styled the season's biggest dress trend with boots and shop polka-dot dresses and knee-high boots to replicate her summer-to-fall look.

On Dua Lipa: Réalisation Sadie Dress ($290); Hermès bag; Chloé Elixir Pendant Necklace ($1050); Jacques Marie Mage Dealan Sunglasses

Shop Dua Lipa's Outfit

Shop Polka-Dot Dresses

Shop Black Knee-High Boots

Always one styling step ahead, I just spotted Dua Lipa out and about in the autumn shoe trend that's set to dominate in just a few weeks' time. Stepping away from the flip-flops and barely-there sandals we've all been living in for the past few months, she instead reached for their antithesis: a pair of knee-high biker boots.

Poised to become one of autumn's biggest shoe trends, biker boots bring a slightly grungy edge to an outfit, which Dua put to work by pairing with a series of light, floaty dresses this week.

Spotted in the new-season pairing, not one, but twice, Dua first styled her Miu Miu Leather Biker Boots (£1890) with Marant Etoile's Preya Embroidered Cotton Minidress (£520), embracing the summer's white cotton minidress trend, all the while nodding to the autumn shoe trend that's yet to come. The chunky Miu Miu boots anchored the lightness of the dress, creating the transeasonal contrast that fashion people return to every year as the seasons begin to shift.

Later in the week, she returned to her Miu Miu boots, pairing them with a black lace-trim slip dress. Finished with a bandana tied over her hair and oversized bug-eye sunglasses, she created exactly the kind of transseasonal outfit I'll be recreating as soon as temperatures begin to dip.

As ever, Dua is a step ahead of the rest. If you're already planning your autumn wardrobe, scroll on to shop the best dresses and biker boots to recreate her looks below.

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My friends are always looking to me for advice on what to buy. Basically, I'm their personal stylist, and I'm responsible for keeping their closets up-to-date with all the latest trends. To tell the truth, I love it, as I get to put my fashion expertise to use. Plus, with the Nordstrom Anniversary Sale 2026 starting July 18, I've got plenty of recommendations—chunky beaded necklaces, lace-trim camisoles, zebra-print kitten heels, silk scarves, cropped trench coats, slim-straight jeans, jelly mules, two-tone earrings, cashmere crewnecks… I can keep going. Heard enough?

Well, don't worry. I put together a curated list of everything trend-forward from the Nordstrom Anniversary Sale that's worth shopping, and they're all pieces I have or would recommend to a friend. Think designer-looking handbags, oversize sunglasses, satin shorts, and so much more. Scroll on to shop these discounted gems.

Shop Trend-Forward Nordstrom Anniversary Sale 2026 Items

Pants are easy. Even dresses are pretty straightforward. But skirts? They pose a bit of a styling problem, especially when it comes to figuring out what shoes to wear with them. For instance, pairing a sundress with sneakers is a tried-and-true combination. But you wouldn't wear those same shoes with a trendy denim pencil skirt or lace-trim slip skirt, would you? Those styles would call for a more sophisticated shoe, like a knee-high boot or pair of kitten-heel slingback pumps. Basically, there are specific shoes that look best with specific skirts, and if you want your skirt outfits to earn compliments in 2026, I've created an outfit guide that's guaranteed to help you achieve that every time.

Below, you'll find 17 skirt outfits that cover every style, from microminis to A-line shapes. In some, the wearer chose to add a pair of boots; in others, they opted for flip-flops. Every look, though, is a winner, so you really can't go wrong if you copy any of them. My tip? Do an inventory of your existing skirt collection first and find any gaps. Fill those in, and then use this guide to help steer you in the direction of the best shoes to wear with each skirt style. Ask any It girl, and they'll tell you that skirts are quietly their favorite fashion item—Miuccia Prada included. So don't get caught wearing them wrong. Not when 17 ways to get them right are just a scroll away.

Best Shoes to Wear With Skirts

Maxi Skirt + Two-Tone Pumps

Long column skirts need two things when it comes to shoes: A color that breaks up the length of the skirt and a substantial heel to add some height. Wearing a black heel with a black skirt can be too much, whereas a two-tone heel remains classic and polished while still offering a bit of contrast.

Embossed Skirt + Ballet Flats

I always thought you needed a taller heel when wearing pencil skirts, but this photo is proof that ballet flats can look just as elevated and chic.

Micro Miniskirt + Pointed Mules

To make your legs look extra long in a micro miniskirt, pair the style with a pointed-toe mule.

Colored Midi Skirt + Strappy Heeled Sandals

In the summertime, a super-strappy sandal can do no wrong, whether you pair it with a mini, midi, or maxi skirt.

Poplin Skirt + Leather Flip-Flops

You can't go wrong with styling a poplin skirt with a pair of sleek leather flip-flops. It's low effort and high reward.

Vintage Skirt + Beaded Sandals

For a touch of fun, style a vintage skirt (like this '90s Prada skirt on Hailey Bieber) with a pair of beaded sandals. They're always a good idea.

Lace-Trim Skirt + Knee-High Boots

One of my favorite skirt-and-shoe pairings of the 2020s is a lace-trim skirt styled with a pair of knee-high stiletto boots. The two just fit together in such a chic, interesting way.

Printed Skirt + White Ballet Pumps

For a casual-cool shoe to wear with a printed skirt, try a pair of white ballet pumps. They're comfortable and offer just the right amount of lift. Plus, they pair well with any color or pattern.

White Skirt + Thong Sandals

You'll find out pretty quickly from reading this story that a pair of heeled thong sandals works with just about any skirt style, but especially white ones. It's a sleek, minimalist approach to skirt dressing that will work every time.

Python Skirt + Patent-Leather Pumps

For a night out, one of the coolest looks to put together is an embossed pencil skirt and pumps, preferably if you wear sheer tights and a knit of some sort. It's a sophisticated and chic combination that will never lead you astray.

Leather Pencil Skirt + Stiletto Boots

For a '90s, Jennifer Aniston–inspired skirt outfit, take a leather pencil skirt and pair it with pointy stiletto boots, preferably a pair with a fitted calf for an extra-sharp look.

Crochet Skirt + Heeled Mules

Heeled mules are another shoe style that works with almost any skirt style, but in 2026, wearing them with a crochet skirt is guaranteed to garner compliments. A leather pair will add a sharpness to the soft fabrication that balances out the entire look.

Drawstring Skirt + Stretch-Thong Sandals

Stretch-thong sandals have become a mainstay for in-the-know skirt wearers for the last summer or two. They're a cooler, more modern take on the traditional heeled thong sandal, and make your legs look miles long.

Leather Skirt + Suede Mules

Suede mules in general will work for this combo, but I must say as an owner of a pair myself, that Manolo Blahnik's Maysale mules are the ultimate buy in this category.

Sheer Skirt + High-Vamp Ballet Flats

There's a risk when it comes to sheer skirts because they can very easily err on the scandalous side, which is fine if that's the look you're going for. If you aren't, though, picking out the right pair of shoes to wear with one is paramount to your outfit's success. One easy winner is a light-colored high-vamp ballet flat, which is classy and polished, balancing out the translucent nature of the skirt style.

Skirt With Hardware + Classic Pumps

If you're opting for a more art-forward skirt with cool hardware or edgy details, your best bet is to go the Prada route by pairing the style with an understated, classic pump. It'll let the skirt do all the work.

Knee-Length Skirt + Thong Sandals

If you want to know that your skirt outfit will work every time, pair a flouncy knee-length skirt with a three-quarter sleeve top and heeled thong sandals.

It's time to put away your sweatpants and leggings because elegant airport style is back. Dressing up for a flight is what every fashion person is doing in 2026, and everyone reading this should follow suit. Don't worry. This doesn't mean you have to wear a dress or something very restricting. The most iconic travel outfits of 2026 so far have been the elevated yet relaxed ones. Think Margot Robbie's Bermuda shorts and mesh ballet flats. This week, though, Daisy Edgar-Jones is giving us inspiration, showing us how to wear jeans and boots stylishly at the airport.

While arriving at CDG Airport in Paris, Edgar-Jones exemplified this idea in a very polished denim outfit. She wore ecru jeans paired with a fitted white tee and a brown leather bomber jacket. To accessorize the look, she opted for black sunglasses and Saint Laurent's leopard-print Mombasa Bag. Grounding the ensemble and proving that footwear doesn't have to be flat to be functional for travel, Edgar-Jones added black pointed-toe heeled ankle boots.

On Daisy-Edgar Jones: Saint Laurent Mombasa Bag ($4000)

I used to only wear leggings and sneakers to the airport, but after seeing how celebrities dress when traveling time and again, I decided it was time to put more thought into my travel outfits and dress up a bit. After all, if I can wear jeans with loafers or a maxi dress with ballet flats to sit at my desk for six hours, why can't I do the same for travel?

All that said, I will be re-creating Edgar-Jones's airport outfit. If you are on the same page, keep scrolling because I've rounded up the chic pieces to get her look, including a variety of elegant heeled ankle boots.

Get the Look

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As the past few weeks have proved, British summer likes to toy with us. Not quite hot enough for bare legs, absolutely too warm for anything resembling a proper coat. So the wardrobe has to put in extra legwork, making outfits feel like summer without the shivering the second the sun goes in. Flip flops and jeans, mini skirts and knits, and boots with just about anything: three core solutions the best-dressed women reach for.

Not the heavy, weather-beaten boots you dragged through February. Not the shearling-lined ones that saw you through December. But a boot that doesn't make you want to cry at the thought of pulling it on in August.

Think a cowboy boot worn with white airy bloomers, a festival-ready knee-high with jorts, or a ruched suede boot paired with your favourite jeans and a simple tee, à la Isabel Marant. Each practical enough to see you through a slightly chillier summer's day without the depressing feeling of reaching back into the winter wardrobe.

And while you're at it: a white cotton mini dress will look considerably more Ibiza-ready paired with brown suede boots than it ever will with sandals. Scroll on for six summer outfit and boots combinations worth stealing.

6 Summer Outfits With Boots Ideas:

1. Chunky Black Boots + Jorts

Style Notes: For a more laid-back look, this chunky black boots, jorts and layered top combination feels fresh without trying too hard. A go-to for festivals, weekend pre-loved trawls or a casual coffee run, you'll be hard-pushed to find a cosy-but-summer look quite as cool.

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2. '90s Square-Toe Boots + Satin Skirt

Style Notes: This Lucy Williams outfit has been sitting in my phone's inspo folder for a good few months and it still doesn't feel tired. Cleverly layered too, it will see you through almost any season; leggings under the skirt come winter being a particularly wise move. Note the muted palette lifted entirely by clashing textures.

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3. Cowboy Boots + Bloomers

Style Notes: If I were to ask ChatGPT to assemble a Pinterest-worthy outfit using only microtrends, it would probably land on cowboy boots and bloomers. Cute meets cool in a way that wouldn't look out of place at Copenhagen Fashion Week. One for the fashion girlies, essentially, and I mean that as the highest compliment.

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4. Lug Boots + Cargo Trousers

Style Notes: One of the main draws of boots in summer is practicality—they are, categorically, more sensible than sandals. You'll only make the mistake of wearing open toes to a farmyard, forest walk or festival once before swapping to full foot coverage. And few looks deliver that casual cool quite like a lug boot and cargo trousers. Especially when layered with a bold knit for chilly mornings.

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5. Riding Boots + Cream Jorts

Style Notes: If, like me and Kate Moss, the only way you can imagine wearing riding boots is with skinny jeans tucked in—congratulations, you're a millennial. Welcome to the modern-day update: riding boots, cream jorts and a chore jacket, a countryside-ready look whether you're actually in the fields or just at Soho Farmhouse.

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6. Suede Boots + Jeans

Style Notes: The Isabel Marant aesthetic will forever sit at the top of the summer dressing moodboard and this outfit pulls in all the best elements: effortlessly cool with a touch of unexpected texture. Suede, denim and a simple white tee is a failsafe combination for any casual occasion.

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Trust Charli XCX to touch down in the chicest, albeit entirely rule-breaking, airport outfit I've seen all season. Ignoring virtually every conventional airport-dressing "do", the singer skipped comfortable track pants and ubiquitous leggings, left cushioned trainers and slip-on Uggs at home and didn't even bother with a wheeled cabin bag. Instead, Charli created a cool-girl travel formula I'd happily wear through Heathrow myself.

Starting with the anti-leggings trouser trend I really didn't expect, Charli ignored every comfort-first travel recommendation and boarded her European-bound flight in a pair of black flared jeans. Skimming the frame before kicking out at the hem, they're hardly the relaxed silhouette most frequent flyers gravitate towards, but they certainly make for a polished look.

Lengthening her silhouette, the singer paired them with sleek black pointed-toe heeled boots. Again, not the most obvious airport choice—particularly when navigating security queues—but the elegant footwear injected a confidence that feels entirely in keeping with Charli's irreverent sense of style.

In one final styling move that's genuinely influenced how I'm thinking about airport dressing, Charli bypassed the standard carry-on suitcase altogether, opting instead for Chanel's Large Tote (£8520) as her travel companion.

Already favoured by some of fashion's chicest dressers, I've been spotting this capacious handbag everywhere lately. A staple in both Kylie Jenner's and Hailey Bieber's wardrobes, the oversized black holdall offers a sophisticated alternative to traditional luggage.

Whilst it may lack the practicality of wheels, the XXL tote more than makes up for it with generous storage space, making it a surprisingly viable option for everything from weekend breaks to longer-haul trips.

Unexpectedly inspired by Charli's rule-breaking airport outfit, I've rounded up the best bags, jeans and shoes to recreate her travel look below.

Shop Charli-Inspired Bags, Jeans and Shoe:

After years of micro-shorts being top of the summer agenda, long shorts started quietly making their presence known last year. From Bermuda shorts to jorts and softly tailored culottes, each of these knee-grazing styles has been spotted in the spring/summer 2026 trend cycle. As the perfect transitional weather solution, their laid-back energy works remarkably well with the lightweight linens and billowing blouses that typically float our capsule wardrobes in summer. So, with the UK days away from a 25-degree spell, what better time to invest in warm-weather pieces than now? But, one question needs to be answered before we do: what shoes do we wear with long shorts in 2026?

Thankfully, fashion people are all too willing to provide us with plenty of inspo. Be it celebrity It girl Amelia Grey styling a pair of calf-skimming Adidas track pants with minimalist glove ballet flats, or Jennifer Lawrence in a three-piece ensemble finished with chic Mary Janes, as it turns out, even the "wrong shoe" works. Think sleek slingback pumps dressed up with lace-trimmed satin shorts, or vibrant tailoring finished with refined leather flip-flops. Almost every shoe works with these transitional heroes, but the seven styles below, in particular, make long shorts look their most stylish.

1. Pointed-Toe Heels

Style Notes: Though I was initially unsure if heels would work, this polished look from Ebony Aroha helped to change my mind. Bloomer shorts are inherently playful, but the classic, structured slingback adds an elegance that pairs well with the pretty lace trims.

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2. Ballet Flats

Style Notes: One of this year's (and every year's) most-worn shoe styles, pretty ballet flats will soften any outfit. Leaning into the elegant nature of summer whites, Nnennae Chem uses her glove flats to ultra-polished effect.

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3. Flip-Flops

Style Notes: Simple yet undeniably effective, the humble flip-flop has quickly become a fashion person’s favourite for one reason: its ease. Whilst the minimalist style allows you to show off your latest pedi, it's also so versatile that there’s yet to be a bottom that doesn’t pair well with a flip-flop. Personally, I’ll be taking cues from Marianne Smyth and styling mine with bright shorts and a fitted tank on warmer days this summer.

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4. Mules

Style Notes: Summer's favourite "ugly" shoe, the chunky mule, is a foolproof choice, especially if you're a pared-back dresser. The quietest way to make a statement with your shoes this season, this slip-on-and-go shoe balances breezy energy with all-day practicality. Plus, they make long jorts and oversized shirts feel far cooler.

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5. Loafers

Style Notes: Pairing well with jeans, dresses and maxi skirts, it's no surprise that loafers work well with long shorts too. With a distinctly preppy polish, pairing long Bermuda shorts with ruched loafers adds an edgier finish. Keeping the rest of her look practical, Millie Holmes layers a fiery red hoodie and denim jacket over a white T-shirt. It's an unexpected outfit, but it works.

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6. Kitten-Heel Sandals

Style Notes: If you live for the summer months, you probably already own at least a few pairs of kitten-heel sandals. More secure than mesh flats or flip-flops, but dressier than a full shoe, the addition of a heel adds a chic edge. Take Marylin’s softly tailored culottes and funnel-neck windbreaker. Sure, the combo would look fine with trainers or ballet flats, but the heel makes it sleeker.

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7. Boots

Style Notes: My personal favourite way to style long shorts has to be with a tall boot. There's something inherently cool about this high/low pairing, and whether you opt for fashion-forward biker boots or a knee-high style, this look isn't afraid to play with proportions. If Sofia Mcoelho’s combo of camo-print shorts and slouchy, suede boots is a touch eclectic for your taste, the pairing works just as well in classic colours and shapes.

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Figuring out the best shoes to wear at the airport is one of the oldest and most heavily unsolved cases in fashion. You want comfort, obviously, but also a shoe style that's easy to remove and put back on after security. The latter is why I've never quite understood why everyone insists on wearing sneakers to travel. They're annoying to remove and take forever to unlace and relace. And don't get me started on when the laces come undone while you're speeding to your gate. It's a disaster waiting to happen. Suffice to say, I'm always on the lookout for good airport outfits to steer my footwear choices in the right direction, and Cannes Airport is my top choice for style-watching, particularly during the Cannes Film Festival. It's where all the chicest people in art, film, sports, and fashion find themselves this time of year, and every last one of them flies in through one place. No wonder I immediately solved my "what shoes to wear to the airport with jeans" predicament after perusing images taken in the arrivals department this week. Naturally, Diane Kruger, a regular at the festival, was responsible.

Kruger, one of the most consistently best dressed attendees of the Cannes Film Festival, arrived at the airport on Tuesday, flying in a casual yet polished travel outfit consisting of a baggy white T-shirt and baseball cap paired with wide-leg black jeans and a pair of brown suede boots by Isabel Marant with a scrunched-down look that made them feel effortless, cool, and comfortable. Never opt for too-tight shoes while flying. They're terrible for circulation. The 49-year-old actress finished off the look with sunglasses and a white Givenchy Voyou Bucket Bag.

On Diane Kruger: Givenchy Small Voyou Bucket Bag ($1990); Isabel Marant Edrik Gathered Perforated Suede Ankle Boots ($1650)

The soft suede and slouchy fit of her boots are really what make them such a smart choice for flying. Paired with loose, equally roomy black jeans, Kruger's boots are easily removable, and the 45-millimeter heel adds elevation without disrupting the shoe's feel. The pointed shape also adds a sense of formality, dressing up her low-maintenance T-shirt-and-jeans pairing and making her look ready for any occasion upon arrival in Cannes—not like she just got off a long flight. Can sneakers do that?

In my experience, the answer is no, so if looking as polished as a Cannes Film Festival attendee arriving in the South of France while you fly off on your Euro-summer vacation this year is the goal, put down your sneakers. A pair of loose black jeans and some suede boots will always be the smarter choice.

Shop Diane Kruger's Airport Outfit

Shop Black Jeans and Suede Boots

When I think of summer fashion, dresses and sandals are what typically come to mind, the slinkier and strappier the better. They're airy and easy, two qualities I look for whenever temperatures rise to peak-summer levels. Or, at least, that was my go-to pairing. In the lead-up to 2026, I've seen a few alternative shoe options that have me questioning my longtime allegiance to sandals, steering my footwear preferences toward another, less conventional shoe trend: moto boots. Apparently, chic girls in their 20s aren't loyal to sandals like I thought we all were, and when they're looking for shoes to wear with summer dresses, moto boots are the style they're grabbing right now. Case in point? Olivia Rodrigo.

The singer, who's gearing up to release her third album, You Seem Pretty Sad for a Girl So in Love, was spotted on June 12 in Barcelona this week shopping with friends ahead of a private concert she'll be performing at in the Spanish city. The 23-year-old wore a black, drop-waist knee-length dress by local Barcelona brand Gimaguas, which she paired with Frye moto boots (specifically, the Campus 14L style), Ray-Ban sunglasses, and a handbag from the Rixo x Dragon Diffusion collaboration. Everyone's talking about the bag in fashion RN, but it was her dress-and-boots combo that immediately caught my eye.

Everyone expects people to style a summer dress like hers with flip-flops or strappy sandals, but her choice to trade them in for edgy boots made her look cooler and more interesting.

Olivia Rodrigo's Look

On Olivia Rodrigo: Gimaguas Leila Dress ($265); Frye Campus 14L Boots ($298); Rixo x Dragon Diffusion Amoria Shoulder Bag ($390)

Next time you're not sure what shoes to wear with a summer dress, especially if you want to stand out instead of fit in, try swapping out sandals for rugged moto boots à la Rodrigo. And don't worry about finding a pair. There are plenty of versions to shop below.

Shop Olivia's Outfit

Shop Summer Dresses and Moto Boots

You don't need a calendar or to go outside to tell it's spring. All you have to do is look at Jennifer Lopez's outfits because she's officially traded her jeans and trousers for floral dresses. Not once but twice in a week, J.Lo stepped out in L.A. wearing a floral dress, and both times she paired it with boots. The first time, she styled her belted maxi dress with beige open-toe boots, and the second time with a cognac knee-high platform pair. While both ensembles looked chic, the second floral dress outfit appeared the most luxurious because of the color of the boots.

The cognac shade is a deep, amber-brown tone. It reads as warm and refined, which is why it looks especially rich on leather boots. Plus, the hue develops a patina over time, making it look more dimensional and vintage-like, which looks chic overall. When discussing J.Lo's look, the boot color paired especially well with her floral dress because it complemented the orange and peachy tones, which fall within the same warm color family.

Beyond J.Lo's specific floral dress, cognac boots pair well with almost all floral dresses. The boot color's connection to natural leather gives it a timeless, versatile nature. And as mentioned, the color deepens and develops character, which is exactly what gives it lasting appeal.

Scroll on to discover my edit of the chicest floral dresses and cognac boots.

Shop Floral Dresses and Cognac Boots

Milan Design Week, also referred to as Salone del Mobile, has undergone a transformation. While it was traditionally an event where interior and home décor brands would debut their new collections for industry insiders, it has recently evolved into a second Milan Fashion Week, if you will. This shift is notable, particularly this year, as more fashion brands enter the design world and unveil their takes on home décor. As a result, the style set (think Alexa Chung and Pernille Teisbaek) is following, turning the city's narrow cobblestone streets into their runways.

Although Who What Wear editors weren't physically present in Milan, we still closely monitored the chic outfits and key trends on display. Ensembles featuring maxi skirts with ballet flats and tailored pants with pumps were certainly present, but the outfit formula we saw everywhere combined light-wash jeans with ankle boots.

Normally, light-wash jeans paired with ankle boots wouldn't catch our attention, but given the weather in Milan was in the 70s, it seemed a bit unexpected. With their structured, enclosed, and heavy nature, the shoes may not define spring style, but it did make sense that fashion people wore them with jeans. The truth is winter hasn't fully let go. In that context of chilly mornings and sudden temperature dips, boots are a practical choice. They also offer support for long days spent walking between Salone events.

The style set also made a case for boots and jeans by choosing a specific boot style—Western-inspired pairs. Western ankle boots offer built-in versatility that other styles lack. The slightly elongated, pointed toe and low, stacked heel make them feel less bulky and more adaptable, pairing well with lightweight jeans as well as flowy dresses and skirts in the spring.

If you're inspired to follow the lead of It girls in Milan who attended Salone, keep scrolling to shop the best light-wash jeans and ankle boots to pair with them.

How People in Milan Are Styling Light-Wash Jeans and Boots

Get the look: red bomber jacket + striped top + light-wash straight-leg jeans + brown ankle boots

Get the look: denim jacket + black T-shirt + low-rise light-wash jeans + suede boots

Get the look: black leather jacket + white button-down shirt + light-wash straight-leg jeans + black ankle boots

Get the look: oversize blazer + white T-shirt + light-wash raw-hem jeans + brown ankle boots

Shop Light-Wash Jeans and Boots

For as long as I’ve worked in fashion, I've looked to Kate Moss for styling inspiration. After decades at the epicentre of the industry, her effortless aesthetic is well-honed and long-admired.

So, you can imagine my delight when I spotted her ready to jet off this week for her trip to the airport. True to form, Moss leaned into her low-key, slightly bohemian sensibility. A pair of roomy, wide-leg trousers anchored the outfit, offering the ease and comfort that long-haul dressing demands. Up top, she kept things pared-back with a simple black vest layered beneath a lightweight printed jacket.

Peeking out from beneath her sweeping hems, Kate styled a pair of sleek heeled boots. Whilst undeniably chic, the practicality of navigating terminals, security queues and sprints to the gate in anything with a heel feels, at best, ambitious. And yet, in true Kate fashion, she made the choice look entirely effortless.

Would I swap my tried-and-true trainers for heeled boots on a travel day? Probably not. But I admire someone who does.

Ready to take the trend for a spin? Keep scrolling to discover the best heeled boots to shop this season below.

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If it weren’t for the runway-fresh Loewe Amazona 180 Bag slung over her arm, I’d have sworn this image of Kate Moss was pulled straight from the mid-2000s archives. Instead, snapped just this week, her look taps into a 2015-era outfit formula I haven't seen in some time.

Starting with a time-stamped foundation, Moss slipped into a pair of leg-grazing skinny jeans. Cut in a classic mid-wash blue, they lend a relaxed, day-time energy to her look. Leaning into a styling trick I’ve long recommended to anyone curious about revisiting skinnies, she paired them with knee-high boots for a sleek, elongating finish.

Up top, she kept things just as nostalgic, an army-green jacket topped her tee, finished with an oversized scarf swirled around her neck.

Between the chunky scarf, the khaki outerwear, and those long-retired skinny jeans, Moss has revived a trio of trends I haven’t spotted on London streets for seasons—if not years.

While it might take me a little longer to fully re-embrace the oversized scarf and utility jacket combination, my denim rotation could use a sharper, sleeker edge, and Moss’s skinny jeans-and-knee-high boots pairing feels like the perfect place to start. Read on to discover and shop the chicest takes on the look now.

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There are very few wardrobe staples that work as hard—or as consistently—as a great pair of black ankle boots. They’re the kind of piece you reach for without thinking, whether you’re getting dressed on a rushed weekday morning or pulling together a last-minute night-out look. And yet, finding the right pair can feel surprisingly complicated. Some are too trend-driven and date quickly, others lean overly practical and miss the mark on shape, and a select few manage to strike that perfect balance between style and wearability.

After spending the past few months paying close attention (on the streets during fashion month, in showrooms, and, admittedly, through a steady stream of recommendations flooding my DMs), it’s clear that not all black ankle boots are created equal. The best black ankle boots don’t just complement an outfit—they anchor it. I constantly rely on my favorite pair every spring, pairing them with straight-leg jeans, trench coats, silk slip dresses, going-out outfits, and everything in between. We love versatility in this house!

Below, shop the best black ankle boots that actually deliver, from timeless investments to the styles fashion people can’t seem to stop wearing.

The Best Black Ankle Boots

• Best Overall Black Ankle Boots: Madewell The Emilie Ankle Boot ($180)
• Best Luxury Black Ankle Boots: Toteme Glossed Leather Ankle Boots ($920)
• Best Under-$100 Black Ankle Boots: Zara Kitten Heel Ankle Boot ($60)
• Best Heeled Black Ankle Boots: Dolce Vita Suzy Booties ($100)
• Best Wide-Width Black Ankle Boots: Margaux Downtown Boot ($485)

Shop My Favorite Black Ankle Boots

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I never thought I'd see the day, but it's officially miniskirt season. I have a few miniskirts I kept tucked away during the winter, and I searched for cool spring shoe trends to style them with while I waited for the snow to thaw. Not much was inspiring me, but one recent outfit finally has. Alana Haim was just spotted wearing an edgy shoe trend with her miniskirt that's been living in my mind rent-free for the past few days: knee-high black leather boots.

Her outfit had cool model-off-duty vibes in spades, and her shoe choice had a lot to do with that. Black leather knee-high boots aren't always considered a spring shoe trend, but this outfit begs to differ. While we all think of boots for winter, I encourage you to consider styling them for spring like Haim did—with a skirt, simple tank top, and shoulder bag. (I would love to also carry a monogrammed Louis Vuitton east-west bag.) Her leather knee-high boots made the look so much cooler, adding a subtly edgy contrast to an otherwise basic look.

If you're into wearing knee-high boots for spring, keep scrolling to re-create this look and shop similar items.

On Alana Haim: Khaite Jett Leather Mini Skirt ($1680); Louis Vuitton bag

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If you've ever attended a college football game, especially in the South, you've probably made an observation or two about what the students wear on game days. As a native of Baton Rouge, Louisiana (Go Tigers!), and now a resident of a very college-dense part of North Carolina, I've been privy to the attire of the college students in attendance more than a few times. For many years, they've gravitated toward the same simple outfit combination: a casual minidress and mid-calf or knee-high Western boots

I don't know how or why this became the go-to game-day outfit, but I recognize the practicality. Football games are often hot—hence the minidress—and you're probably going to do a lot of walking between the car you arrived in, your tailgate spot, and the stadium, hence the walkable Western boots. But it's not an outfit combination that's exclusive to college football stadiums, as Margot Robbie just proved while heading into West Hollywood hot spot The Bird Streets Club on a very warm day in L.A. over the weekend.

Specifically, Robbie paired a strapless black knit dress by With Jéan with slouchy Western boots by Khaite. As for extras, Robbie carried a brown leather bomber jacket and her go-to bag as of late, the Chanel 25. All in all, she looked incredibly chic (as she always does), and the outfit was as appropriate for a trip to L.A.'s most exclusive members-only club as a game day. How's that for a versatile outfit combination?

Keep scrolling to see Robbie's take on the outfit and shop similar pieces for wherever the warm days to come take you.

The Outfit on Margot Robbie

On Margot Robbie: Petar Petrov The Sentinel Jacket ($4300); With Jéan Luca Dress ($239); Khaite Clive Leather Boots ($1680); Chanel 25 Bag; Persol PO1024S Sunglasses ($630)

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Gen Z It girls have patented the boots-with-skirts formula. The hallmarks of a well-done outfit lie in the balance between edgy and preppy. Exhibit A: A sheer lace skirt must be paired with a suede knee-high boot. Exhibit B: A pleated miniskirt should always be countered by a chunky moto boot. Follow this, and you'll find getting dressed this spring a breeze.

While the unexpected pairing might seem obvious to some, let me break it down. The boot is a remnant of chic winter outfits whose sole duty is to protect against elements, that is, the unpredictable spring forecast. One day it's in the mid-70s, and the next it's below freezing. The skirt: It's a signal to the fashion set that summer is just around the corner.

Keep scrolling to shop the cool-girl outfit formula and how the fashion set, from your favorite Gen Z celebs (hi, Iris Law) to IG's It girls are styling boots-with-skirts outfits this spring.

7 Chic Boots-with-Skirts Outfits for Spring 2026

1. Suede Midi Skirt + Kitten-Heel Boots

Style Notes: Midi skirts have my heart. One: They are the perfect-length skirt to wear with boots. Two: They are incredibly easy to style. I love this double-layered neckline.

2. Animal-Print Skirt + Knee-High Leather Boots

Style Notes: From leopard to Dalmatian, animal print is in. Complement the funky print with a graphic tee and a pair of skin-tight leather boots.

3. Slip Skirt + Suede Tall Boots

Style Notes: Break up an all-black outfit with texture focused accents like a utility belt, suede boots, or bangle stack.

4. Sheer Lace Skirt + Block-Heel Boots

Style Notes: NYC It girl Aïsha Farida styled her sheer lace skirt and suede knee-high boots with a Y2K-style hack (a long-sleeve under a crewneck tee).

5. Miniskirt + Chunky Boots

Style Note: The Iris Law is my go-to for cool Gen Z celeb outfits. The miniskirt-and-chunky-boot 'fit is next on my list to re-create. I love the use of texture, the ruffles on the skirt, the embroidered knee-high socks, and the cropped jacket over a soft knit.

6. Knee-Length Skirt + Campus Boots

Style Notes: Call it the CBK effect—knee-length skirts and knee-high boots are a spring 2026 outfit formula you can find on every It girl's IG feed. Bonus points if you style it with a fitted button-down.

7. Pleated Skirt + Moto Boots

Style Notes: East Coast prep meets grunge—the wonders a pair of moto boots and a pleated miniskirt and do. Pair with a striped rugby shirt for an added flair.

I've been living in Brooklyn for a few years now and love the personal style of everyone I pass by. I find myself asking passersby the details of their outfits, especially their shoes. This year, spring is taking a longer time than usual to hit my favorite borough, but I've been preparing anyway. I noticed during our short stint with the sun, aka Fool's Spring, boots were still everywhere.

Boots don't have to be limited to winter, but I was caught by surprise at the number of people still wearing boots. I'd assume people would wear sandals, heels, flip-flips… but then it hit me: These boot trends will be everywhere once spring has officially arrived. From moto boots to animal-print, boots will still be a major spring trend.

If you're into wearing boots for spring, keep scrolling to see outfit inspiration and shop all the trends.

Moto Boots

These boots are everywhere. My best friend and one of my neighbors has a pair. During all my café and errand stops, I keep seeing this edgy trend styled with casual outfits and leather jackets, namely. Moto boots are so back for spring.

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Slouchy Boots

Slouchy boots are so chic to me. They marry an outfit seamlessly by adding texture without having to try hard. Effortlessly cool is always the vibe we're going for in Brooklyn.

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Kitten-Heel Boots

If there's one shoe I see religiously worn around my block, it's a kitten-heel boot. Since winter, it's been a major trend in NYC, and it's clearly a fan favorite for spring, too. I'm wearing my pair with shorts and a tank top for an edgy, cool-girl vibe.

Shop Kitten-Heel Boots

Animal-Print Boots

This trend is definitely for the bold and brave dressers. If you're not much of a print person, I suggest trying animal-print boots with a simple outfit like below. You can also pair them with jeans or pants and have the print as a slight pop to zhuzh up your outfit.

Shop Animal-Print Boots

Tan Boots

If you're not into white boots for spring, tan boots are the perfect alternative. This hue is a neutral that truly blends into an outfit and is also great to wear for transitional weather.

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Walking the River Seine, shopping along the Champs-Élysées, and people-watching from a brasserie are all prime spots to see chic Parisians in their natural habitat. Unlike any other city I've been to, Paris holds a special place in my heart for its fashion, its love, and its people, who, speaking of which, are so in touch with the latest trends that they often popularize them first.

We're only a few months into 2026, and as spring begins to blossom, the Parisians have already set the standard for spring 2026. Whether it's commenting on the in and out trends French women are adopting in 2026 or showcasing the best shoes to wear with jeans, there's no denying the Parisian style set has a knack for providing fashion advice.

This week, I took a look at my shoe rack and noticed there was definitely room for improvement, specifically in the flat-shoe department. So as any good shopping editor would do, I went to the IG accounts of my favorite French women for inspiration. I, of course, made sure to write up my findings. And that's exactly what's coming to you below.

Scroll on to shop the six French-woman flat-shoe trends I expect to be everywhere come spring. From classic Mary Janes to unexpected booties, the Parisians know where it's at.

6 French-Woman Flat-Shoe Trends for Spring 2026

Half-Boots

Chic but cool—the moto half-boot is an unexpected French-woman flat-shoe trend for spring 2026, yet it makes total sense. In contrast to the boots' edgy attitude, French women are styling them with icy blues and stark whites for a springtime effect. Score extra points with the style set if you tuck your trousers into the boot.

Red Mary Janes

Red flats are synonymous with the French woman. Capitalize on the Frenchness and wear them with capri pants and a crisp white button-down. Throw on a matching red lip, and you're ready to walk to the Champs-Élysées. This time of year always calls for a pop of color. Take a page out of the French woman's style book and invest in a pair of red Mary Janes.

Glove Flats

The glove flat is a French woman's staple. Often worn with low-rise trousers or straight-leg jeans, the simple look and fitted silhouette make styling easy. Pro tip I stole from a chic Parisian: Wear them with sheer tights if you want to look like a fashion person.

Mules

A mule is my solution to looking chic and feeling comfortable. It gives the illusion of a ballet flat with the ease of a house slipper. Bonus points if it comes in soft suede or crochet.

Lo-Pro Sneakers

It's rare to spot a Parsian in such a casual shoe like a sneaker, but if you do, chances are high it's a low-profile silhouette. Succinct and minimal, styles like the Onitsuka Tiger Mexico 66 and Adidas Tokyo Shoes make for an excellent choice.

Ruched Loafers

Ruched loafers have always held a spot on the French woman's shoe rack. But lately, the slim silhouette has been hitting different and seems to be preferred over sneakers or Mary Janes for its sturdy stability and elegant appeal. Parisians are styling the loafer with low-rise trousers for an old-money-meets-new look.

Why Trust Us?

At Who What Wear, 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 recognizable names in fashion. Every item we recommend is carefully selected based on current trends, quality, and real-world wearability.

We regularly try pieces ourselves, including everything from best-selling jeans to designer shoes; speak to external experts and fashion insiders; and stay closely connected to what our readers are searching for. Our advice is grounded in expertise and has to pass our exceptional taste levels—so you can feel confident in every recommendation.

When I tell you that I've spent the last week scouring every single runway show from the fall/winter 2026 season, zooming in on look after look to bring you this guide to fashion month's most memorable shoe trends, I'm not being dramatic. It's a labor of love, and one I'm happy to do. Shoes, after all, are kind of my weakness, so every minute I spent dissecting them on the runway for all of you is just as much for my own selfish means. Let's just say there's a hefty fall 2026 shoe wish list forming—and no, my wallet is not ready.

My callouts? High-vamp pumps continued to dominate, with an especially strong showing during New York Fashion Week at Michael Kors, Calvin Klein, Khaite, Proenza Schouler, and Tory Burch. Polished animal prints were another standout, appearing at Saint Laurent and Jil Sander. Plus, if you're getting married next fall, consider your "something blue" handled, with little blue shoes proving to be on every designer's mind right now. Matthieu Blazy at Chanel and Pieter Mulier at Alaïa did them best. That's not all, of course. There are lots more shoe trends where those came from, all of which can be found below.

Fortunately, for anyone not patient enough to wait until fall to start shopping the shoe trends that debuted on the fall/winter 2026 runways, many of the best ones are available to shop already. Keep scrolling to get started.

Fall/Winter 2026 Shoe Trends

High Vamps

Ever since Phoebe Philo's Club Slippers arrived on the shoe scene last year, fashion people have been enamored with high-vamp pumps—and it showed on the fall/winter 2026 runways, particularly in New York. Tory Burch, Calvin Klein, Proenza Schouler, Khaite, and Michael Kors all debuted versions of their own, garnering plenty of attention online, as attendees made comparisons and decided which pairs they'd be purchasing come fall. What makes this shoe so desirable? It's comfortable, especially the low-heel versions made by Philo and Reformation.

Fierce Prints

Animal prints for fall? Not exactly groundbreaking. Somehow, though, brands like Jil Sander, Khaite, and Saint Laurent still managed to create fresh-feeling animal-print footwear to debut at their respective fall/winter 2026 shows in Milan, New York, and Paris. A pointed toe dipped in snakeskin, an experimental "leopard" pattern, and a high-vamp shape all contributed to making fierce prints gain back a sense of newness that fell away after so many seasons of the same old styles trending.

The Boots

There are boots, and then there are *the* boots that debuted on the fall/winter 2026 runways in Paris and New York, in particular. Tom Ford's show by Haider Ackermann (his second for the brand) was stocked full of sleek, sexy stiletto boots paired with pencil skirts—a combination that will be everywhere come fall. Khaite and Schiaparelli, too, included this sophisticated yet edgy boot silhouette, only adding to its appeal.

Something Blue

This trend isn't just for brides, but if you are getting hitched this fall, you'll have no trouble finding your "something blue." Just walk into your closest Chanel or Alaïa and take your pick. From satin ballet flats at Carven to knee-high, hand-stitched feather boots at Prada, there was no shortage of blue footwear on the runways this season, making for a fun, unexpected shoe trend worth investing in come autumn.

Twice Toned

The two-tone shoe trend has always been run by Chanel, but Matthieu Blazy's version transformed the style from a forever classic to an It item—*the* It item. It started with his spring/summer 2026 shoe offering for the French house, which is currently going viral online as fashion people fight over stock in Paris (and now, New York and more cities). The fall/winter 2026 shoe collection, though, is arguably even stronger, and two-tone styles are included throughout. Whether you're looking for ballet flats, pumps, or even boots, brands like Ferragamo, Ulla Johnson, and, of course, Chanel, have you covered,

Royal Jewels

Last season, rhinestones were encrusted on footwear at Prada and more. Now, for fall, brands are taking a subtler approach, coloring their shoes in rich, luxurious jewel tones. Moody shades of royal purple, jade green, sapphire, ruby, and tourmaline were scattered throughout this season's collections, at Ferragamo, Jil Sander, Balmain, Balenciaga, Zankov, Carolina Herrera, Christian Dior, and Khaite. Essentially, the royal jewels were everywhere—or better yet, will be everywhere come fall 2026.

Timeless T-Straps

Sometimes, a classic shoe just needs a brand or two to reinvent it to give it some life and a new era, which is exactly what happened at Christian Dior, Calvin Klein, Givenchy, and Jacquemus with T-strap heels. We all probably have (or have had) at least one pair in our closets, but they've likely been gathering dust. Now, unique styling options and playful colors, twists, and patterns have made T-strap heels feel fresh again.

Thigh-Highs

We often see thigh-high or over-the-knee boots on runways due to their high-impact look, but rarely do pairs that actually feel wearable debut, and this season, those are the exact styles we saw grace the runway at Chloé, Hermès, Khaite, and Ralph Lauren. It's really all about styling and finding ways to make over-the-knee boots look approachable but still like a statement. At Khaite, models donned them with just coats, as if to replace pants, and at Hermès, they were styled with leggings and tunics, giving the combination from the early to mid-2000s a much-needed update.

A Satin Touch

Satin shoes for fall might be risky, but after looking through all the pairs that debuted on the fall/winter 2026 runways this fashion month, I'm too in love with my options to care about what's "practical." Carven, Michael Kors, and Schiaparelli all debuted art-like footwear options in soft, shiny satin, as did Nº21, Zankov, Sandy Liang, and Loro Piana.

Why Trust Us?

At Who What Wear, fashion is our specialty. 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 recognizable names in fashion. Every item we recommend is carefully selected based on current trends, quality, and real-world wearability.

We regularly try pieces ourselves, including everything from best-selling jeans to designer shoes; speak to external experts and fashion insiders; and stay closely connected to what our readers are searching for. Our advice is grounded in expertise and has to pass our exceptional taste levels—so you can feel confident in every recommendation.

After spending a lot of time in Paris and Rome, Zoë Kravitz has finally made her way to New York. She's been spotted in the city heading to meetings and hanging out with her boyfriend, Harry Styles, who is hosting Saturday Night Live this weekend. While we, of course, enjoy seeing her hand in hand with Styles on the streets, as fashion people, we especially love looking at the paparazzi images and taking notes of her casual everyday outfits.

Among the maxi dress and ballet flats she was seen wearing on a warm, spring-like day, Kravitz has been spotted twice in the same trousers and boots. Specifically, they are black bootcut pants and elongated square-toe ankle boots from The Row. The first time she was seen in the pants and boots, she styled them with a white button-down shirt, a long, lightweight beige coat, Saint Laurent's Le 5 a 7 Bea tote, and The Row sunglasses. The second time, she paired the pants and boots with a windbreaker-style jacket layered under a beige fur-trimmed wrapped coat. She accessorized with the same designer bag and sunglasses.

On Zoë Kravitz: The Row Carla Booties ($1470); Saint Laurent Le 5 a 7 Bea Bag($4100)

Ditching her go-to baggy Still Here Sport Jeans for tailored, anti-denim pants with a bootcut hem might seem like a big change, but it makes sense. Celebrities, editors, and stylish It girls have been gravitating toward slim-fitting pants that gently hug the legs and relax at the hem for a few months now. This pant trend is as versatile as jeans and makes even the simplest outfits look polished. As Kravitz shows, these pants pair best with sleek ankle boots because they sit smoothly over the shoe without revealing skin. Plus, the pointed toes stand out, unlike ballet flats that can get lost, and the slim design balances the wide hem of the pants, creating a pleasing proportion.

Kravitz's recent black-tailored-pants–and–ankle-boots look offers all the spring outfit inspiration needed. She's styled them in a way that makes you want to skip your favorite jeans. If you're as convinced as I am, keep scrolling to discover and shop the best bootcut trousers and ankle boots.

On Zoë Kravitz: The Row Carla Booties ($1470); Saint Laurent Le 5 a 7 Bea Bag($4100); Arcteryx Atom Jacket ($280)

Shop Bootcut Trousers and Ankle Boots

The feeling of spring is finally in the air, and for those of us in New York especially, the excitement is palpable. We're getting through the days by looking forward to shedding winter layers and swapping our favorite jeans or trousers for skirts. The pencil skirt, a fitted, knee-length silhouette that tapers from the waist to the hem, is the trend currently dominating our thoughts. Its clean, sophisticated aesthetic and runway endorsement—seen in the spring 2026 collections of brands like Khaite, Saint Laurent, and Tory Burch—have made it a favorite among fashion insiders. While versatile with a range of footwear, the current go-to pairing for the best dressed women is knee-high boots.

It girls like Bella Hadid and Hailey Bieber are championing the pencil-skirt-and-knee-high-boot combination. During Paris Fashion Week, Hadid was spotted in a vintage Fendi skirt and a white long-sleeve shirt, elevated with tan heeled knee-high boots and a suede Prada tote. Meanwhile, on her trip to Tokyo, Bieber wore a leather pencil skirt styled with a leather blazer, a V-neck sweater, and black sock-like knee-high boots.

In the past, the styling rule dictated that the skirt hem had to overlap the top of the boot to create a polished, streamlined look. However, in 2026, Hadid and Bieber are challenging this idea. They demonstrate that showing your kneecaps is now the chic way to go. Plus, it provides a welcome bit of breathability on warmer spring days.

If Hadid and Bieber have inspired you to embrace the pencil skirt trend and pair it with knee-high boots, keep scrolling because I've curated an edit of the best styles for both.

On Bella Hadid: Fendi skirt; Dôen Lidie Tee ($178); Saint Laurent Francoise Leather Knee-High Boots ($2150); Prada Bonnie Bag ($3650)

Shop Pencil Skirts and Knee-High Boots

If you’re looking to refresh your spring denim rotation, I have just one recommendation: cigarette jeans. After seasons dominated by puddling hems and ultra-baggy silhouettes, the pendulum is swinging back, and slim-fitting, slightly cropped cigarette jeans are reclaiming their place as the fashion person's favourite.

Streamlined, but not fussy, this neater silhouette is easier to dress up than slouchy styles, whilst also lending itself to a broader range of occasions. Making my case, Olivia Rodrigo was spotted out this week in a mid-blue pair cropped just above the ankle, cut in a clean stovepipe fit, which she wore styled simply with a white T-shirt layered beneath a black fur-trimmed jacket.

Of course, it was her footwear choice that really caught my eye. Rather than reaching for trainers or barely-there heels, Rodrigo grounded her jeans with glossy black square-toe boots. The structured shape bridged the flash of skin that the cropped hemline would otherwise reveal, creating a smooth, uninterrupted line from hip to toe. The squared finish, meanwhile, added a directional edge that round or pointed styles just can’t quite replicate.

While temperatures are still lingering on the chilly side (and my sandals remain firmly boxed away), square-toe boots feel like the most elegant partner for cigarette jeans right now. If you’re as convinced as I am, keep scrolling to shop the best cigarette jeans and square-toe boots to wear together this season.

Shop Cigarette Jeans and Square-Toe Boots:

As the weather warms, hemlines rise, and fabrics get lighter, it’s opportune to pause and take stock of the sartorial bounty that spring brings. With the season synonymous with lightweight cottons designed to be frolicked through bucolic grounds and balmy blouses as airy as the breeze itself, there’s no better moment to consider the ensembles you’ll be wearing throughout the months ahead.

And as contrary as it might sound to the images that this time of year evokes, those who have already made an early start on outfit planning are indicating that it’s actually boots that will dominate.

Sturdy and serviceable, boots aren’t the shoe style you’d typically partner with your floaty blouses or flirty skirts. Indeed, these pieces are best reserved for something more relaxed and nimble, like a ballet flat or heeled flip-flop.

But as fashion has proven time and time again, what’s more desirable than the least expected? So, if these pilot silhouettes are an indication of what’s to come once spring has fully bloomed, it’s clear that boots will continue to carry over from winter for a few more weeks.

But not all boots are made equal. And despite tastemakers still seeking out the sensibility and structure of these flat-footed options, they’re looking for styles that bring a softness and levity. After all, when your weekends begin to look like long al fresco lunches, strolling through farmers’ markets and ‘picky bitting’ your way through every stretch of verdant greenery that your city has to offer, you need something that’s as utilitarian as it is unfussily chic.

Ahead, Who What Wear UK has compiled a guide to the biggest boot trends prevailing for spring 2026. With ease, fluidness and functionality in spades, these are shoes that’ll have you taking the phrase “touch grass” literally.

6 Key Boots Trends for Spring 2026

1. Speed Drive

Style Notes: If Alexander Skarsgård’s turn as a controlling biker in rom-dom Pillion has you wondering whatever happened to the motorcycle aesthetic, you wouldn’t be alone. After accelerating onto the runways through staples like Miu Miu’s moto boots and Saint Laurent’s leather bomber, it seemed that everyone was clambering to dress as if they'd just raced Daytona.

However, for spring 2026, the trend is shifting into gear and taking a more sleek form. Instead of overt buckles or stomper platforms, the look is being rendered through a more delicate lens with slimmer soles and more calf-hugging fits.

Shop the Trend:

2. Crinkled Leather

Style Notes: Where there are open roads, there are also high seas. Much has already been discussed about the rise of the buccaneer aesthetic, from Alexander McQueen’s skull scarf to Chloe’s ruffled-front shirts. However, the most fitting part of this aesthetic is Vivienne Westwood’s famed Pirate boots. First appearing in the British designer’s autumn/winter 1981 collection—and previously before that on open waters from the 17th Century—a renewed interest in the shape has brought slouchy boots back with a vengeance.

Still, for spring 2026, the key pieces are less Captain Jack Sparrow-inspired and more interested in the gathered element itself. Invest in a style with a delicious wrinkled effect—the patina across the leather will make them look far more vintage–and sits high enough up the leg to allow you to tuck the hem of your jeans into.

Shop the Trend:

3. Rachel Green Curves

Style Notes: Of course, one of the most defining facets of the spring 2026 season is the industry’s renewed interest in the past. Nevertheless, rather than coming at it from a nostalgia standpoint, this historical interest is more about mining the archives for new designs. One trend that is bucking this format, however, is curved boots.

A major style for spring, the combination of the rounded toe and curved toes is reminiscent of the pared-back minimalism and effortless preppiness of Rachel Green’s wardrobe from Friends. The internet might currently be besotted with Carolyn Bessette Kennedy’s outfits, but let's not forget that before there was interest in her Calvin Klein denim and Prada knitwear, Jennifer Aniston’s New York costuming reigned supreme.

Shop the Trend:

4. Fluted Heels

Style Notes: Still, there’s always a place for a ‘90s Manhattan moment, in our humble opinion. With spring styling requiring less thought than that of autumn or winter, lean into your instincts with looser fits, neutral colours, like the tan style seen here, and boots that can take you down every side alley and avenue of your city.

But where the rest of your outfit might be more casually assembled, put the right foot forward in a pair of fluted heels. Pinched at the top and tapered at the base, these will add extra comfort for days spent on the move, and a subtle visual element that makes them more intriguing to the eye.

Shop the Trend:

5. Mesh Well

Style Notes: With the mercury climbing and skies clearing, entering this period of lightness and ease is akin to emerging out of hibernation. So, shed the layers and take every chance to catch a glimpse of the sun’s rays on your bare skin, even whilst wearing boots.

Opting for a style with mesh elements is not only a surefire way of adding a touch of romance and insouciance—two cardinal characteristics of springtime—but also makes it clear that we’re past cold-weather days marked by afternoon sunsets and frigid temperatures. The dog days are over, indeed. As for what lies ahead? Something more carefree and ethereal.

Shop the Trend:

6. Rodeo Redux

Style Notes: Cowboy boots might’ve once been commonplace in the wardrobes of ranch handlers roaming up cattle in Wyoming, cutters riding stallions through the prairies of Montana or those travelling along the Oregon Trail.

However, with contemporary endorsements from perennial horse girls and supermodels like Kendall Jenner and a city-approved makeover from New York downtown darling Khaite, this Western-influenced style has since become a part of the modern uniform. Think of this as a rodeo redux—a revival that takes the best of the original, but without the overt farmyard motifs.

Shop the Trend:

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.

I don't know about you, but I live in denim outfits all year long. Before a new season rolls around, I begin my usual hunt for fresh ways to style my favorite jeans with a special focus on the shoe options. Naturally, I turn to the fashion people in my life and on my Insta feed for inspiration, and I am happy to report that the shoe trends this spring are incredibly chic. Plus, they can be worn for many seasons to come.

After a good scroll session, I narrowed in on seven of-the-moment shoe styles that are perfect for pairing with jeans come spring. They range from casual to dressy, yet they are all comfortable without sacrificing style—something that I highly value when it comes to putting together my wardrobe. Think everything from cool Adidas sneakers and flip-flops to V-cut flats and kitten heels. Keep scrolling to shop my top picks for each shoe trend alongside visual outfit inspiration for how to wear them.

Sneakers

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V-Cut Flats

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Slingback Heels

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Flip-Flops

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Animal-Print Shoes

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Loafers

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Kitten-Heel Boots

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Bootcut jeans are officially back in the conversation, but it's not in the way you remember them. In 2026, the silhouette feels sharper, cooler, and far more intentional, largely thanks to how fashion people are styling it from the hem down. The difference between dated bootcut jeans and a chic pair comes down to footwear, and right now, shoes are doing most of the heavy lifting. Think less nostalgic throwback and more modern polish with silhouettes that balance the flare just enough to make the entire outfit feel current.

The chicest looks pair bootcut jeans with shoes that elongate the leg and ground the slight flare without competing with it. Sleek pointed-toe heels are leading the charge, especially refined pumps and minimalist slingbacks that peek out just enough beneath the hem. Fashion insiders are also leaning into sharp kitten heels and low, sculptural heels for daytime—proof that you don't need sky-high stilettos to make bootcut jeans look elevated. The key is a streamlined toe shape and shoes that feel intentional rather than bulky.

For a more relaxed take, 2026's fashion set is reaching for polished boots and directional flats that keep proportions in check. Think slim ankle boots with a subtle heel, refined ballet flats with a modern edge, and even almond-toe loafers styled with a longer inseam. When done right, bootcut jeans suddenly feel like the most versatile denim silhouette in your closet, effortlessly balancing structure and ease and proving that the right shoe choice makes all the difference.

Shoes to Wear With Bootcut Jeans

The shoe style: Pointed-toe leather ankle boots

The shoe style: Light suede ankle boots

The shoe style: Ballet flats

The shoe style: Block-heel ankle boots

The shoe style: Suede tan ankle boots

The shoe style: Nude slingback heels

The shoe style: Brown heels

The shoe style: Metallic heels

The shoe style: Pointed-toe leather boots

The shoe style: White pointed-toe heels

The shoe style: Stiletto ankle boots

The shoe style: Heeled sandals

The shoe style: Block-heel Mary Janes

The shoe style: White ankle boots

The shoe style: Patent-leather heels

Blue denim adds a classic vintage spin to any ensemble, and white trousers offer a crisp, fresh feel. Still, New Yorkers are looking in the other direction, gravitating toward a cooler, edgier option: black jeans.

The moody trend is most often spotted in a relaxed wide-leg silhouette, giving off a chic, nonchalant vibe. Still, cigarette styles and bootcut picks are just as popular, and the hue anchors the look.

There isn't just one shade of black when it comes to jeans, either. Stone-washed variations, deep hues, and charcoal designs coexist, allowing for wardrobe customization. The selected intensity mingles with the rest of the outfit, propelling the look into a polished or grunge direction.

However, successfully donning brooding jeans doesn't end with choosing a shade of black. Knowing how to style them is key, especially when it comes to footwear. Slip on the wrong shoes and your It-girl pants may look dated. Thankfully, NYC trendsetters are giving a master class on the best way to style black denim.

From the West Village to Williamsburg, the coolest women are pairing their vampy pants with chisel-toe boots. In between square-toe and pointed-toe styles, the exaggerated front barely peeks out from underneath the hemline, elongating the leg. A slight heel adds just the right amount of height while staying walkable.

This foolproof outfit combo easily translates from the office to happy hour and may even pass the night out test. Keep reading to secure the jeans-and-boot look that's all over New York.

Shop Black Jeans

Shop Chisel-Toe Boots

When it comes to shopping for standout basics, Zara is always one of my first stops. Some may argue that the iconic brand doesn't just have its finger on the pulse; it seems to be able to foresee what we would like before we've clued into it. I love getting a jumpstart on my outfit rotations for any upcoming season. It takes out the guessing game of what I will be regularly wearing. So for spring 2026, I took a stroll through the Zara site for some fresh basics to help round out my closet.

Needless to say, I came across some incredible basics that I couldn't wait to share with you. Think everyday pieces like T-shirts, jeans, trench coats, and loafers, to more of-the-moment finds with sheer fabrics, lace, and other details. Take a moment and keep scrolling to shop 27 of the best basics you'll want to live in for the next three months.

Shop the Best Zara Basics for Spring 2026