Wondering How to Dress If You're Over 50? Just Look to These Mature Fashion Icons With Impeccable Style

Personal style can be mastered at any age—there is no magic number or milestone birthday that can claim to be the pivotal point. Some lucky fashion lovers manage to find their signature look early on and hold onto it throughout their lives, adjusting and updating it ever so slightly to suit the changing times and trends. For others, understanding the outfits and clothes you feel most comfortable in can be a more arduous and experimental process.

Whichever camp you reside in, there's no denying that your tastes and wardrobe needs change as we age. As we get older, and therefore wiser, I've now realised that all of the cheaper and trend-leaning items I bought in my 20s haven't stood the test of time. (Hello, American Apparel disco pants.) So, in an attempt to consume less and buy better, I'm endeavouring to only purchase items that feel truly "me"—items I can see myself wearing for the next half-century, if I give them the tender love and care they deserve.

This is something I learnt close to home. My mum, who is in her 70s, is still supremely stylish, but she doesn't have the same need for smart dresses, skirts and suits on a regular basis due to the fact, she's retired and her day-to-day activities are quite different now. That means she's still getting to grips with casual attire, and it's been a process for someone who loves getting dressed up. But looking to the plethora of stylish celebrities who are over 50, they've all proven that growing up doesn't mean we need to ditch the things we loved in our youth for styles that appear more intrinsically "matronly" or "womanly".

Style Notes: Julia Roberts attends the 47th Annual Golden Globe Awards on January 20, 1990 at Beverly Hilton Hotel in Beverly Hills, California.

Style Notes: Julia Roberts attends the Gucci Ancora runway show during Milan Fashion week on September 22, 2023 in Italy, wearing a similar look to something she wore three decades prior.

No matter what stage of life you're in, I'm a big believer that you can wear whatever you want, whenever you want. There shouldn't be "rules" or "dos" and "don'ts" just because you're older or younger. Societal norms are shedding left, right and centre, and never before has it been cooler to age while staying true to yourself. Many of the most admired and most iconic women in the fashion industry haven't done a complete 180 on their favourite looks just because they've hit 40, 50, 60 or more.

As Who What Wear UK's own Poppy Nash explains in her column that rounds up the best expensive-looking high-street finds both she, a 29-year-old managing editor and her mum, a 59-year-old former fashion buyer, adore, "there are genuinely so many polished, premium-looking pieces that work for both of us, despite the 30-year age gap."

A real tastemaker will be guided by what feels right, but we all have wobbles and moments of uncertainty. So whether you're a 20-something trying to find that ultimate timeless outfit or a 50-something rediscovering a love for colour and searching for quality inspiration for the season ahead, our gallery of over-50 celebrities, industry figures and influencers will help. Read on for 36 trailblazing women who prove that chic style has no limitations.

The 36 Over 50 Fashion Icons Who Define Timeless Style

1. Cindy Crawford

Style Notes: Some outfit combinations never go out of style, and supermodel Cindy Crawford proves it with the enduring allure of this creation with a blazer, jeans, and heels. It works for everyone at every age and for multiple occasions.

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2. Jennifer Aniston

Style Notes: From the moment she broke through to the mainstream in her preppy Ralph Lauren wardrobe as Rachel Green in Friends, Jennifer Aniston has always been a beacon of style. I adore this look from 2024, where she attended an event for The Morning Show wearing a summery Reformation dress and this decade's answer to her most famous haircut.

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3. Demi Moore

Style Notes: Demi Moore's personal style has changed a great deal over the years, but she's on a particularly great roll at the moment, thanks to her recent press tour for The Substance and impeccable wardrobing from her stylist Brad Goreski. (We're still thinking about her iconic sheer dress!) This Gucci ensemble, however, really ticks so many boxes and will no doubt inspire you to carry your love of suede throughout the seasons.

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4. Pamela Anderson

Style Notes: From Baywatch to Barbwire, Pamela Anderson has a fashion legacy so potent that her filmography evokes such a vivid image of her most iconic looks—a red swimsuit darting across Malibu beach, a leather corset and knee-high stilettos. At 57, however, Anderson has embraced her softer side for a look she describes as more authentic to her roots, ditching the bombshell glamour makeup and pink fluffy Ivy Supersonic hat for a natural complexion and a capsule wardrobe full of Proenza Schouler suits and Viktoria & Woods satin shirts.

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5. Oprah

Style Notes: From wearing the most spectacular pink Stella McCartney dress to the royal wedding through to her regular high-profile appearances, where waist-nipping dresses or skirts with tops play the main role, Oprah Winfrey is always chic. I love this casually luxurious street style look the most, proving that wardrobe staples like navy jumpers and pinstripe trousers will always be a worthy investment.

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6. Cate Blanchett

Style Notes: We could all gain a thing or two from Cate Blanchett's style philosophy. The 55-year-old is a firm believer that clothes are meant to be reworked and reworn over the course of your lifetime, with the Australian actress regularly reprising silhouettes she's previously been spotted in for major red carpet appearances. When she does wear 'new', she ensures it's sustainable, like the time she wore a Hodakova top made from 102 recycled spoons. But I'd say her off-duty wardrobe is where she's taking the most leaps and bounds, including her excellent Tár-inspired suits and the time she wore a bedazzeled slogan t-shirt that read: "Wow, what a sh*t show.”

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7. Sandra Bullock

Style Notes: Sandra Bullock has been serving up incredible looks for years. This woman is a red carpet pro, and along with incredible gowns, she gives us loads of street style inspiration, like this structured look with a glint of colour blocking.

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8. Monica Bellucci

Style Notes: Monica Bellucci is often considered to be one of the most beautiful women in the world. The actress started off modelling for the likes of Dolce & Gabbana and Dior, but then made her mark in films such as Malèna and, more recently, Beetlejuice Beetlejuice. Her style is very elegant with figure-flattering dresses that pay homage to her Italian upbringing and tailored shapes.

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9. Jennifer Lopez

Style Notes: While Jennifer Lopez chalks her ageless appearance down to rigorous exercise and olive oil skincare, there's no doubt that the 55-year-old certainly uses a few nifty styling tricks to achieve the fountain of youth. For instance, pairing flared jeans with the cropped Chloé blue jacket to create an hourglass effect.

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10. Diane Von Furstenberg

Style Notes: The legendary designer might be known for her wrap dresses, but her own closet extends far beyond that. Diane von Furstenberg is a master of print clashing—she makes modern pieces look elegant by placing them next to classics.

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11. Grace Jones

Style Notes: If outré is your fashion genre, then Grace Jones must be your leader. The always-outrageous performer has never dialled down her madcap outfit ideas, and for that, we will always be grateful.

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12. Viola Davis

Style Notes: You'll most commonly see Viola Davis in one of two combinations in public: A smart trouser suit or a pared-back sheath dress in a bold hue. Here, she is doing the latter and chintzy black dresses for all ages.

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13. Halle Berry

Style Notes: When Halle Berry arrived on Elie Saab's runway in the same gown she wore when receiving her historic Best Actress Oscar in 2002, it really cemented how more than two decades had passed and yet Berry looks no older now than she did then. Magic? Perhaps. An incredible beauty routine to maintain her stunning complexion. Certainly. But, best of all, a sassy-or-nothing approach to dressing complete with sheer fabrics and risqué silhouettes.

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14. Sarah Jessica Parker

Style Notes: As iconic as Carrie Bradshaw is—her designer wardrobe, countless rosettes and endless newsboy caps—Sarah Jessica Parker's own style evolution is worthy of the same level of accolades that her fictional counterpart receives. The impact she made on the industry is palpable, from Réalisation Par's Collette dress, which was inspired by a piece she wore to an event in 1999, but no more resounding than her work in endlessly uplifting the Fendi Baguette. Here's to investing in a designer bag and continuing to wear it forever.

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15. Carine Roitfeld

Style Notes: For top Parisian outfit inspiration, look to editor in chief and legendary stylist Carine Roitfeld. She knows great, versatile separates when she sees them.

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16. Julianne Moore

Style Notes: Fashion over 50 doesn't have to reinvent the wheel. This glorious Bottega Veneta look, complete with leather-disguised-as-denim jeans and a mohair flannel shirt, is the perfect accompaniment to Julianne Moore's instantly recognisable red hair. The revered actress often chooses simply cut clothes in striking shades and prints. Whether on the red carpet or the street, and the formula works to great effect.

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17. Nicole Kidman

Style Notes: Quintessential feminine silhouettes are what we associate with Nicole Kidman. While her work with Balenciaga has seen her in some more ironic styles, like a t-shirt emblazoned with her own face, her go-to wardrobing, including ankle-tied heels and lace dresses, makes her our go-to for prettier styling.

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18. Carla Bruni

Style Notes: Carla Bruni has lived a thousand lives. From her time on the runway in Karl Lagerfeld's Chanel tweed and Gianni Versace's baroque designs to her indie folk music career and recent stint as France's former first lady, Bruni adapts to different decades and stylings with ease. Now, at 57, her silhouettes are always sleek, refined and effortlessly polished.

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19. Pat Cleveland

Style Notes: As one of the original supermodels and a leading figure of 1970s fashion, it's no surprise that Pat Cleveland still has a spectacular and ultra-glamorous wardrobe. The American fashion insider never shies away from decadent fabrics, over-the-top jewellery and true entrance-making party outfits.

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20. Kate Moss

Style Notes: While she's only just entered her 50s, Kate Moss is a '90s fashion icon who never fails to inspire and set trends. From her collection of leopard print coats to jet black skinny jeans—hallmarks of her indie sleaze era—to the more bohemian slip dresses and ruffled blouses, she tilts between rock chic to ethereal whimsy with an ease that only just gets more aspirational.

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21. Isabelle Huppert

Style Notes: Parisian actress Isabelle Huppert is the very definition of chic. Of course, it helps that she's French—you know how much we love their style—but she always looks effortless, whether that's wearing a couture gown at Cannes or a more androgynous suit at fashion week.

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22. Celine Dion

Style Notes: Singer extraordinaire Céline Dion is a prime example of finding your more adventurous fashion side later on in life. Over the past few years, she has become a bona fide fashion fanatic and a trailblazing trendsetter, wearing all of the latest collections and wildest pieces first. (See: Stylist Law Roach putting her in Vetements' Titanic hoodie for Paris Fashion Week). We bow down.

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23. Michelle Obama

Style Notes: We miss the regularity with which we used to see Michelle Obama in so many different outfits. Since the former FLOTUS has been out of the White House, we still get the occasional glimpse of her fantastic midi-dress and suit collection, but we're taking it back with this Preen look. It's still a fun but appropriate option years later.

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24. Helen Mirren

Style Notes: Actress Helen Mirren is a national treasure for many reasons, but aside from her theatrical skills and film repertoire, we are also huge fans of her event-dressing prowess. It's basically go big or go home, like this fabulous Oscars moment.

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25. Iman

Style Notes: Forever chic, model Iman has always erred on the side of minimalism. She often adds a dash of interest via accessories, but you can always rely on her for an outfit that easily translates IRL.

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26. Doria Ragland

Style Notes: Whether she realises it or not, Meghan Markle's mother, Doria Ragland, was jettisoned to mother-of-the-bride outfit icon back in 2018. We're looking forward to potentially seeing more of the super-chic lady in the future, but for now, just take note of her classic-but-still-interesting ensemble that she wore on the big day.

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27. Renia Jaz

Style Notes: Many moons ago when we first spotted Renia Jaz's blog, Ven's Wife Style, we immediately had to know more. From donning an all-grey outfit made fun with a faux-fur bag to doing the Balenciaga look better than seasoned street stylers, her smart but sassy style has us hooked.

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28. Caryn Franklin

Style Notes: The iconic TV presenter, author, activist and stylist (amongst many other things) is one of our all-time-favourite women over 50 for striking outfit combinations that really speak to her personal style ethos of buying better, buying less and generally being more conscious in your consumption—without losing your cool. You can see more of Caryn Franklin's style via our "Best Wardrobes in Britain" shoot.

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29. Natalie Massenet

Style Notes: As the founder of Net-a-Porter, former editor Natalie Massenet is a queen of fashion. The impeccably dressed entrepreneur artfully combines new-season prints with classic wardrobe staples for an ultra-elegant finish.

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30. Ruth Chapman

Style Notes: As MATCHESFASHION.com's co-founder, Ruth Chapman is an industry-adored figurehead with access to the best designer garms going. Take away the fancy clothes, and you still have a woman who oozes serenity and elegance. Her style choices are often classic with a twist, like this demure blouse rendered in metallic fabric.

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31. Paula Sutton

Style Notes: Way before cottagecore was a thing, Paula Sutton was already doing this trend in her country pile. Her style remains consistently chic, made up of elegant cotton dresses, chunky teddy coats and sleek trousers paired with midi-heel courts.

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32. Naomi Campbell

Style Notes: From the moment she graced the modelling scene at just 16 years old in the late '80s, Naomi Campbell blazed her own trail. Quintessentially British with a tongue-and-cheek humour and penchant for pairing miniskirts with tights, chunky shoes and fur coats, the supermodel brings a sense of grace, elegance and ironic poshness to every look.

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33. Gwyneth Paltrow

Style Notes: From bringing quite luxury to the masses with her courthouse looks to the burgundy Tom Ford for Gucci suit that defined a decade, Gwyneth Paltrow's style only gets better with age. Though she's swapped silk co-ord sets (like the one she wore in Great Expectations) for her own label's collard shirts, her casual Californian take on mature fashion is one we love keeping up with.

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34. Victoria Beckham

Style Notes: Victoria Beckham has come a long way since she catapulted onto the stage in her Spice Girls days wearing little black dresses and a decade-defining bob. There's been her 2000s era—a little commotion for her "WAG" dressing, wearing England team singlets with Hermés Birkin—and her 2010s bandage dress reign featuring her spiky blonde pixie cut. But now in the 2020s, we love her commitment to a puddle pant, sharp blazer and flowing blouse, proving that personal style is a path that's anything but linear.

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35. Chloë Sevigny

Style Notes: Chloë Sevigny is the name that comes to mind whenever someone utters the phrase 'It Girl'. Her career began in the 1990s when she appeared in a slew of independent films, cementing her as a downtown darling in the New York style scene. Now, you can catch her galavanting around the island of Manhattan, mixing emerging designers with established labels and proving that personal style doesn't have to die after 50.

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36. Courteney Cox

Style Notes: As Monica Geller on Friends, Courteney Cox's wardrobe was always more streamlined and minimal compared to Rachel's more yuppie styling and Phoebe's whimsical wardrobe. Off-screen, this is something the actress has continued throughout her personal life, too, with the 60-year-old often wearing classic shapes in monochrome hues. It's this choice that makes her outfits look quite timeless, as the pieces she wears aren't tied to a specific date or decade.

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How to Dress When You're Over-50?

Struggling to dress and find your personal style as you hit this milestone? The simplest way to feel your most authentic self and rediscover your own taste is to begin with a well-edited wardrobe. As you'll notice, many of the older fashion icons in this edit all follow a similar style ethos—one that prioritises pared-back minimalism and well-tailored essentials.

To this point, there are a few capsule wardrobe staples that can never go astray. These include a fabulously crisp button-down, which can be styled with jeans à la Celine or layered over a sumptuous silk tank top for a more relaxed look, a polished skirt that can be dressed up or down and a great coat. (Because when all else fails, at least you can wrap yourself up in something gorgeous and call it a day.)

These simple but effective additions are a surefire way to set you on a path that will have you feeling—and looking—the best you ever have.

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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.