Move Over, "Clean Girls"—These are the Enduring Icons Behind Every Great Autumn Fashion Trend

The leaves are crisp, the mornings are fresh and you (might) have turned your heating on. It's official: autumn is upon us. After months of easy linen, lightweight dresses and barely-there layers, the arrival of autumn is always an excuse to take stock and rethink our wardrobes, but perhaps most importantly, the way we put our outfits together. Layering is practical, of course, but a great coat can be the entire outfit. Knitwear is no longer a relegated to being an afterthought, and, the right pair of boots can make even jeans and white tee feel like a statement. But for me, some of the best autumn outfit inspiration doesn't come from the runway, but from those who have already mastered the art of sartorial story telling.

Across TV, film, music, and fashion, there is no shortage of brilliant and well-dressed women, both real and fictional, who strike that elusive balance between looking effortlessly elegant and weather-appropriate. Their wardrobes might not be full of the most directional pieces, but the way they combine timeless staples, thoughtful accessories and a few of the season's key trends makes their style and legacy so compelling. Where would we be without Jane's roomy Birkin? Kate Moss' maxi dresses and shaggy furs? The Gilmore Girls' brand of cosy chic?

This autumn, we're taking cues from the style icons who make transitional dressing look particularly good. From the sophisticated city dressers to the comfy girls with a penchant for outerwear and clever layering, these are the women to have on your radar when you're wondering what to wear as the seasons change. Whether you're looking for inspiration for your next office outfit, a weekend look or simply a new way to wear the pieces already hanging in your wardrobe, consider this your guide to the autumn style set worth really watching—plus the outfit ideas we'll be recreating in 2026.

1. The GIlmore Girls

Style Notes: If there was ever one fictional wardrobe that feels mosy synonymous with autumn, it has to be Gilmore Girls. Set against the cosy, small-town backdrop of Stars Hollow, the comfort-watching series is full ofinspiration for anyone who believes that the best autumn outfits involve plenty of '90s coded knitwear, thrown on jackets and a generous dose of nostalgia. From Rory’s preppy staples (think fitted roll necks, pleated skirts, and loafers) to Lorelai’s dressed down denim, leather jackets, oversized knits and polished boots, the magic in the styling is all in the layering: nothing feels overly "done", it's just the familiar, easy ensembles that we all crave once September rolls around. Just add a takeaway coffee, a plaid scarf and a crisp walk through the leaves, and suddenly the Stars Hollow aesthetic doesn't feel like such a throwback.

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2. Jane Birkin

Style Notes: Think of quintessential Jane Birkin and you may be conjuring up images of undone blouses, baskets and micro minis, but her approach to autumn dressing is just as moodboard-worthy. What has cemented her status in the halls of fashion history is her knack for making simple pieces feel chic, and when the temperature drops, her worn-in denim, soft knitwear and relaxed tailoring come into full effect. An oversized jumper here, a lived-in jacket there, minimal accessories, always (and often finished with tousled hair), Birkin was the queen of nonchalance, and her autumn aesthetic proves that the secret to great cold-weather dressing might simply be mixing and matching old staples for that extra je ne sais quoi.

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3. Claudia Winkleman

Style Notes: As dedicated Traitors fans will know, Claudia Winkleman's series wardrobe has become almost as discussed as her trademark fringe. It's a simple formula, but wonderfully low-key: chunky knits, opaque tights, ankle boots and plenty of black, usually softened with cosy textures and the occasional checked or printed layer; in short the pieces you may well own. And, as the show is shot in the Scottish highlands, practicality is key, but for any of the more dramatic moments (round tables, especially) you can expect boxy silhouettes and the kind of accessories that will sell out the day after airing. For anyone looking to build a chic autumn wardrobe that prioritises comfort, character and timeless staples over fleeting trends, Winkleman is a particularly compelling source of inspiration, there's a good reason her look already is so iconic that it's become a halloween costume.

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4. Sade

Style Notes: Before there was "quiet luxury" there was Helen Folasade Adu. In an era of new romantics, club kids and rocks, Sade’s style was the kind of effortless elegance that was ahead of it's time. With a wardrobe built around clean lines, fluid tailoring and a restrained palette (it's rare to see her outside of cream, black and denim blue), the same silky blouses, perfectly cut trousers and oversized jackets that she championed in the '80s and '90s have come back around now. There’s a sense of ease to everything she wears, but never anything accidental—each look feels considered without looking overly styled. Add her signature hoops, sleek hair and red lip, and you have a masterclass in quiet glamour that still feels remarkably modern today, just Solange Knowles, Tracee Ellis Ross or Rosie Huntingdon Whiteley.

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5. Princess Diana

Style Notes: More than just a "revenge dress". Princess Diana’s downtime wardrobe is the perfect example of how to make even sporty separates feel regal. We all remember her oversized blazers pleated skirts, and riding boots, but it was the jersey sweaters, jogging bottoms and caps that gave her off-duty looks the perfect balance of polished and relaxed. Sweatshirts and shirts, smart, tailored coats and tracksuits, and leggings and heels might feel like a regular occurrence today, but Diana paved the way for the paparazzi conscious A-list to try the high/low approach.

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6. Kate Moss

Style Notes: Few models are as known for what they wear off the runway as Kate Moss. Say the words "Glastonbury" or :"leopard coat" and a mental roster of her best looks come to mind, proof that she is one of British fashion's most enduring muses.
Her signature formula? Rock ’n’ roll staples with bohemian classics: slim black jeans, maxi dresses, ankle boots and a statement coat thrown casually over the top. She’s never one for looking too polished (and if she looks like she just got out of bed looking impossibly well rested, even better). Always undone but endlessly influential, the secret to great autumn style the supermodel way is simple silhouettes, a subtle colour palette and an eye for detailing.

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7. Monica Geller

Style Notes: Everyone is quick to fangirl over Rachel Green's outfits in Friends, but when it comes to autumn style, Monica Geller is hard to match. Where Rachel and Phoebe are decidedly more trend-lead, Monica's style tends is punctual and precise as the character herself. Think fitted knits, turtlenecks, high-waisted jeans, smart skirts and jackets, often grounded in a muted palette of black, grey and autumnal browns. Don't call her "boring" through, the occasional print will sneak it's way in, or an accessory like a hat or a great boot will keep things interesting. For an autumn wardrobe that leans classic, comfortable and quietly chic, her latter looks remain an excellent source of inspiration for desk to dinner.

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8. Charlotte Rampling

Style Notes: Charlotte Rampling's turn on the AMI menswear runway in 2023 should tell you just how beloved by the fashion crowd she truly is. It's not often that a 77 year old woman gets the celebration she deserves, but Charlotte Rampling has long perfected the kind of understated style that only gets better with age. Clean tailoring, pared-back knitwear, crisp shirts and beautifully cut trousers might feel British in their suiting heritage, but she has a French nonchalance when it comes to layering dark neutrals and minimal accessories to allow the clothes—and her unmistakable presence—to do the talking. Whether she’s in a sharply tailored, masculine suit like her runway finale look, or '60 shift dresses, Rampling proves that great style isn’t about following trends; it’s about knowing what works for you and wearing it with confidence.

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9. Anna Scott

Style Notes: Minimalists, rejoice! Julia Roberts’ character wardrobe in Notting Hill is the ultimate lesson in late ’90s understated dressing. Long before Ryan Murphy's American Love Story put CBK back on the mood boards of women everywhere, Anna Scott's covert uniform of a leather blazer, fitted T-shirt, straight-leg jeans, and sleek black accessories changed the way we wanted to dress. .Throughout the movie her colour palette stays pretty much the same—plenty of black, cream, denim and icy pastels (she's a celeb in hiding after all). But rewatch after rewatch you'll be surprised just how well it holds up nearly 30 years later, inspiration for our own shopping approach.

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10. Iman

Style Notes: It takes a lot to stand next to David Bowie and hold your own, but Iman's supermodel style makes her a legend in her own right. Rooted in strong silhouettes, impeccable tailoring and a very healthy dose of glamour, she's best known for her sleek ’80s power dressing, fluid evening gowns and his-and-hers off-duty looks. Our favourite thing about Iman? She’s never afraid of proportion, whether that means a dramatic shoulder, a sweeping coat or wide-leg trousers, while rich neutrals and jewel tones give her wardrobe sophisticated polish. Given the era in which she rose to prominence, accessories play an equally important role (and yes, that often means statement earrings and oversized sunglasses)but her looks are so beautifully curated and immaculately presented that nothing ever feels excessive. The result is a wardrobe that feels confident and glamorous without being dictated by trends—a masterclass in using great tailoring, striking proportions and a signature sense of individuality to create truly memorable style.

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