The Over-50 Fashion Icons With the Freshest 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.

Over 50 fashion and clothing inspiration: Jennifer Aniston wearing a green blazer and carrying a Chanel bag

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Jennifer Aniston shows off her preference for tailoring in an evergreen blazer and black high-waist trousers. Oh, and we wouldn’t mind borrowing her Chanel bag either. 

Whichever camp you reside in, there's no denying that as you get older, your tastes and wardrobe needs change. For example, aged 33, I now realise that all of the cheaper, trend-ticking items I bought on the high street in my 20s haven't stood up, so I'm endeavouring to buy less and buy better. 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.

Over 50 fashion and clothing inspiration: Carla Bruni wearing a black tuxedo

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Carla Bruni looking sharp in a black tuxedo and stilettos.

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 180 on their favourite looks just because they've hit 40, 50, 60 or more.

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 interview outfit or a 50-something rediscovering a love for colour and searching for quality inspiration, our gallery of over-50 celebrities, industry figures and influencers will help. Read on for 35 trailblazing women we love to take fashion tips from on the regular.

Julianne Moore
Over 50 fashion and clothing inspiration: Julianne Moore in a lilac jumper and trousers

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Style Notes: Fashion over 50 doesn't have to be boring. This glorious lilac look is the perfect accompaniment to Julianne Moore's instantly recognisable red hair. The revered actress often chooses simply cut clothes in striking hues, whether on the red carpet or the street, and the formula works to great effect.

Key buy:
Lucinda Chambers
over 50 fashion and clothing inspiration: Lucinda Chambers in a white dress and black bomber jacket

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Style Notes: Lucinda Chambers, former fashion director of British Vogue, has spent over three decades at the forefront of the fashion industry. It's no surprise, then, that she's managed to hone her look. From bold prints to chunky necklaces as well as chunky shoes, this is easy sophistication to wear at any age.

Key buy:

The chunky loafer is fast becoming a wardrobe staple.

Oprah Winfrey
Over 50 fashion and clothing inspiration: Oprah wearing a white coat with a beige shirt dress and kitten heel pumps

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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. 

Key buy:

Wear this classic shirt dress with knee-high boots, or elegant heels. 

Alyson Walsh
Over 50 fashion and clothing inspiration: Alyson Walsh wearing a leopard coat with a utility jumpsuit

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@thatsnotmyage

Style Notes: If you're looking for polished style with a trend-led twist, Alyson Walsh is your woman. The fashion journalist turned influencer packs plenty of Scandi cool with clever minimalist pairings and the odd flash of print. 

Key buy:
Pat Cleveland
Over 50 fashion and clothing inspiration: Pat Cleveland in a red satin skirt and cape with bold jewellery

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Style Notes: As one of the original supermodels from the 1970s, 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, OTT jewellery and true entrance-making party outfits.

Key buy:
Grece Ghanem
over 50 fashion and clothing inspiration: Blogger Grece Ghanem in a white Gucci tee with leopard trousers

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@greceghanem

Style Notes: Grece Ghanem is one of our favourite Instagram obsessions. The Montreal-based personal trainer has the best designer clothing collection and wears all of the latest pieces in the most unexpected ways without being wacky. For starters, take this Gucci tee with leopard trousers.

Linda Fargo
over 50 fashion and clothing inspiration: Linda Fargo wearing a white jacket and trousers

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Style Notes:  As senior vice president of the fashion office and the director of women's fashion and store presentation of New York's iconic Bergdorf Goodman, Linda Fargo is often spotted wearing winning outfits. She also has a love of Dior's red lipstick, Holiday. Speaking to the Financial Times, she revealed that she's a fan of timeless classics "with a bit of bite."

Key buy:

A fresh white blazer will go with everything from tailored trousers to floaty dresses. 

Isabelle Huppert
over 50 fashion and clothing inspiration: French actress Isabelle Huppert wearing a printed Chloé blazer with brown flares

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Style Notes:   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.

Key buy:

This vibrant red will inject colour into classic wardrobes. 

Halle Berry
over 50 fashion and clothing inspiration: Halle Berry wearing a short black lace dress

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Style Notes: It's hard to believe Halle Berry is over 50. I'm sure she looks younger than me. The Hollywood star takes an all-sassy-or-nothing approach to dressing, often choosing see-through fabrics and risqué silhouettes. 

Monica Bellucci
over 50 fashion and clothing inspiration: Monica Belluci looking chic in a black dress from Dior

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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 The Matrix Reloaded. Her style is often very elegant with figure-flattering dresses.

Key buy:

This dress will hug you in all the right places. 

Renia Jaz
over 50 fashion and clothing inspiration: Ven's Wife Style wearing a printed midi skirt with a white shirt and blue satin shoes

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@venswifestyle

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.

Key buy:

The vivid blue and silver embellishment makes a beautiful pairing.

Viola Davis
over 50 fashion and clothing inspiration: Viola Davis wearing a shocking pink gown

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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 vibrant hue. Here, she is doing the latter and reclaiming Barbie pink for all generations of women. 

Maye Musk
over 50 fashion and clothing inspiration: Maye Musk wearing a yellow brocade dress with silver shoes

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Style Notes: The mother of SpaceX and Tesla founder Elon Musk, Maye Musk has been a model for five decades. Her style is sleek and minimal, but when she heads out for an event, she goes all out with something like this. You need to know that she has great taste in earrings, lipstick, roll-necks and dogs.

Jennifer Aniston
Over 50 fashion and clothing inspiration: Jennifer Aniston in black tailoring

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Style Notes: The Jennifer Aniston superfans out there will know that the Friends star has always stuck to the same idea: wear all black and you'll always look good. She's not wrong. Whether its a sparkly LBD or a more mix-and-match tailored look like this, this method works.

Key buy:

Another beautiful offering courtesy of Reformation.

Anna Wintour
over 50 fashion and clothing inspiration: Anna Wintour in a leather coat, printed dress and knee boots

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Style Notes: Vogue's Anna Wintour has a few wardrobe pillars (in many iterations) that have been cemented over the years to create the hardest-working wardrobe in the biz. One of her classic looks is a fabulous coat, printed dress and knee boots.

Carine Roitfeld
over 50 fashion and clothing inspiration: editor Carine Roitfeld wearing a knotted blue shirt with a pencil skirt and pink pumps

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Style Notes: For top Parisian wardrobe inspo, look to former Vogue Paris editor in chief and legendary stylist Carine Roitfeld. She knows great, versatile separates when she seems them.

Key buy:

A knee-length midi can be styled many ways, but we love Carine's tied shirt and bold shoe look. 

Diane von Furstenberg
over 50 fashion and clothing inspiration: designer Diane Von Furstenberg in a leopard print bomber jacket and pencil skirt

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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.

Key buy:

Leopard print is a classic that Diane approves of.

Michelle Obama
over 50 fashion and clothing inspiration: Michelle Obama wearing a blue and yellow lace Preen dress

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Style Notes: We miss the regularity with which we used to see Michelle Obama in so many different outfits. Since the former FLOTUS has not been in the White House, we still get the occasional glimpse of her fantastic midi-dress collection, but we're taking it back with this Preen look. It's still a fun but appropriate option years later.

Demi Moore
over 50 fashion and clothing inspiration: Demi Moore in yellow checked trousers and a pink coat

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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. This colourful ensemble really ticks so many boxes and will no doubt inspire you to be braver in combining different shades.

Key buy:

Pair with bold colours like Demi, or stick to muted tones for a minimalist look. 

Caryn Franklin
over 50 fashion and clothing inspiration: Caryn Franklin wearing a green puffy-sleeved Osman top with a black skirt and sneakers

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Phill Taylor

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.

Key buy:

You'll rewear this gorgeous green hue for years to come. 

Natalie Massenet
over 50 fashion and clothing inspiration: Natalie Massenet wearing a metallic blazer with black skinny jeans and studded pumps

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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.

Key buy:

A chic finishing touch to any look. 

Grace Jones
over 50 fashion and clothing inspiration: Grace Jones in an all-black outfit with a spotty hat

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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.

Cindy Crawford
over 50 fashion and clothing inspiration: Cindy Crawford in jeans and a blazer

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Style Notes: Some outfit combinations die hard, 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.

Key buy:

This oversized version can be thrown over any look to add a tailored touch. 

Ruth Chapman
over 50 fashion and clothing inspiration: Ruth Chapman wearing a silver blouse with black trousers

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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.

Key buy:
Helen Mirren
over 50 fashion and clothing inspiration: Helen Mirren in a pink tulle gown

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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 2019 moment.

Iman
over 50 fashion and clothing inspiration: Iman in a black leather blazer and trousers

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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.

Brigitte Macron
over 50 fashion and clothing inspiration: Brigitte Macron in a pastel blue suit and white T-shirt

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Style Notes: The interest in Brigitte Macron's wardrobe stretches far and wide, with many having a particular interest in the French first lady's denim choices. We, however, are very into her sharp trouser suits and how she styles them: Note the T-shirt instead of a blouse or button-down.

Key buy:

This bold blue suit is a real contender. 

Doria Ragland
over 50 fashion and clothing inspiration: Doria Ragland at Meghan Markle's wedding wearing a pale green coat and dress

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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.

Céline Dion
over 50 fashion and clothing inspiration: Celine Dion in a blue blazer, red jumper and skinny trousers

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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. We bow down.

Sandra Bullock
over 50 fashion and clothing inspiration: sandra bullock

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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 hair and makeup inspiration. 

Key buy:

If your wardrobe isn't calling for the addition of a gown, take inspiration from vibrate hues and design details. 

Cate Blanchett
over 50 fashion and clothing inspiration: cate blanchett

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Style Notes: Is there anyone who seems to be having as much fun with fashion as Cate Blanchett right now? The star has recently been pictured out and about wearing some incredible blouses and high-waisted trousers, and we're here for it. 

Nicole Kidman
over 50 fashion and clothing inspiration: nicole kidman

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Style Notes: Ladylike style is always what we associate with Nicole Kidman. From ankle-tied heels to lace dresses, she's our go-to for prettier styling. 

Key buy:

You'll find yourself making plans just to wear these.

Jennifer Lopez
over 50 fashion and clothing inspiration: jennier lopez

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Style Notes: No, Jennifer Lopez does not look like she's 52. She doesn't even look like she's 40—let's be honest. Her style has remained consistent throughout the years, but this recent all-leather look has to be one of our favourites.

Key buy:

The design and maroon hue looks very high-end.

Paula Sutton
over 50 fashion and clothing inspiration: paula sutton in a teddy coat and a pair of leggings and white shirt

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@hillhousevintage

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. 

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

Next Up, The Autumn/Winter 2023 Fashion Trends That Really Matter