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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With a slightly psychedelic print, Rixo's leopard-print coat is beloved by tastemakers and style insiders who prefer their pieces to feel both timely and dated to a certain point in time.
Jennifer Lawrence has been trotting all through Manhattan in a coat near similar to this one these past few months.
Fur faux-fur trim and lace stockings make this an exceptional outfit in its own right, but made even better when you know it has Alexa Chung's tick of approval.
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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A funnel-neck like no other, this Mango coat achieves that sleek, minimalistic sense that's synonymous with the decade with a longline shape and belted finish.
When it comes to bootcut jeans, this Paige style earns my tick of approval every time.
Made with real eel skin, these loafers are the epitome of refined craftsmanship.
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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Winona Ryder was so ahead of the curb with her collarless jacket, and this Toteme style feels entirely ageless.
When it comes to anything-but-basic-basics, Leset truly fits the bill.
With an emphasis on comfort and clean-cut shapes, these COS trousers are fluid and functional.
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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From two titans of British fashion—M&S and 16Arlington—comes a satin-trim blazer worth investing in.
Elevate your white shirt with this perfectly cut style from With Nothing Underneath.
A hallmark of the decade, these pinched straight-leg jeans from Agolde look like they have stepped straight out of the '90s.
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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If money were no issue, this is what I'd be wearing day in and day out.
On a more accessible level, this Mango coat is equally snug.
Make like Carrie Bradshaw and invest in high-low dressing by pairing this coat with a lavish clutch, like an intrecciato leather style from Bottega Veneta.
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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A coat style owned by everyone from Jennifer Aniston to Kate Moss.
Très chic.
Sock boots are the style of the season—you heard it here first.
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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Brushed knitwear is all the rage this winter.
A French-inspired iteration that is endlessly elegant.
Watch this space—the tie-up coat is back.
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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Add some contrast to your outfit with this velvet shirt.
One of the best satin skirts on the market.
Such a great city stomper.
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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The asymmetrical cut through the lapel is so pleasing to the eye.
Invest in your basics, and you'll never put a bad outfit together again.
These hit at just the right length at the ankle, and petite women need not worry about taking them to the tailor as they're also offered in an extended size range.
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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Inspiring more than just our teenage bedrooms, Sofia Coppola is clearly ahead of her time in this fur-trimmed cardigan.
An LBD is such a '90s hallmark, and this modern version is done so beautifully.
The director did live in Paris for several years, so it's only fitting I shout perenially chic French fashion brand Sézane.
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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Straight from the runway, right into your closet.
The pinstripe on this style adds such a refined element to your look.
It would be remiss of me to not show you the matching trousers, too.
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