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.

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.

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 staying true to yourself. Many of the most admired and 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 42 trailblazing women we love to take fashion tips from on the regular.

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:

Chinti & Parker Purple Pop Aran Merino Wool Sweater (£295)

Former fashion director of British Vogue Lucinda Chambers 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 Marni shoes, this is easy sophistication to wear at any age.

Key Buy:

Miu Miu Logo-Embossed Rubber-Trimmed Leather Sandals (£540)

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 is always chic.

Key Buy:

Stella McCartney Leilani Belted Vegetarian Leather-Trimmed Wool-Flannel Shirt Dress (£1050)

If you’re looking for a 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:

Ashish Single-Breasted Leopard-Pattern Sequin Coat (£2255)

As one of the original supermodels from the 1970s, it’s no surprise that Pat Cleveland still has a spectacular and ultra-glamorous wardrobe now. The American fashion insider never shies away from decadent fabrics, OTT jewellery and true entrance-making party outfits.

Key Buy:

Gucci Embellished-Collar Jacquard-Stripe Lurex Dress (£2600)

Grece Ghanem is our latest Instagram obsession: 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. Take this Gucci tee and leopard trousers example, for starters.

Key Buy:

Gucci Sequin-Embellished Cotton-Jersey T-Shirt (£620)

Senior vice president of the fashion office and the director of women’s fashion and store presentation of New York’s iconic Bergdorf Goodman, Fargo is often spotted wearing leopard print. 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:

Vivienne Westwood Lou Lou Virgin-Wool Cady Jacket (£990)

Actress Isabelle Huppert is the very definition of chic. Of course, it helps that she’s French (and 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 with an overcoat at fashion week.

Key Buy:

Balenciaga Hourglass Floral-Print Wool-Crepe Blazer (£2590)

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.

Key Buy:

Dundas Sequinned-Panel Georgette Mini Dress (£387)

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 the film such as The Matrix Reloaded. Her style is often very elegant with figure-flattering dresses.

Key Buy:

Roland Mouret Hisley Draped Crepe Dress (£950)

When we spotted Renia Jaz’s blog, Ven’s Wife Style, we immediately had to know more. From the all-grey outfit made fun with a faux-fur bag flourish to doing the Balenciaga look better than seasoned street stylers, her smart but sassy style has us hooked.

Key Buy:

Wandler Lotte Faux Pearl-Embellished Satin Mules (£162)

You’ll most commonly see Viola Davis in one of two combinations in public: either 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.

Key Buy:

Oscar De La Renta Strapless Bow-Embellished Silk-Faille Gown (£6192)

The mother of Space X and Tesla founder Elon Musk, Maye 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.

Key Buy:

Preen by Thornton Bregazzi Tessa Ruffled Floral-Print Satin Dress (£298)

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-‘n’-match tailored look like this, this method works.

Key Buy:

COS Backless Knitted Slip Dress (£79)

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.

Key Buy:

Max Mara 101801 Icon Double-Breasted Wool and Cashmere-Blend Coat (£1580)

For top Parisian wardrobe inspo, look to former Vogue Paris editor in chief and legendary stylist Carine Roitfeld.

Key Buy:

Raey Dip-Hem Silk-Satin Slip Dress (£180)

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

Key Buy:

Sara Battaglia Leopard-Print Double-Breasted Jacket (£201)

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 almost four years later.

Key Buy:

Alexander McQueen Draped Cotton-Faille Midi Dress (£1760)

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:

Whistles Eleni Check Wide Leg Trouser (£75)

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 Franklin’s style via our Best Wardrobes in Britain shoot.

Key Buy:

Mr Mittens Ribbed Wool and Cashmere-Blend Sweater (£450)

As the founder of Net-a-Porter, former fashion 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:

Gianvito Rossi Portofino 70 Suede Sandals (£575)

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

Key Buy:

ASOS Design Denim Square Neck Fitted Jumpsuit in Washed Black (£38)

Some outfit combinations die hard, and supermodel Cindy Crawford proves it with the enduring allure of this blazer/jeans/heels creation. It works for everyone, at every age, and for multiple occasions.

Key Buy:

Balmain Black Double-Breasted Wool Blazer (£1650)

As‘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:

Saint Laurent Long-Sleeved Metallic-Striped Blouse (£1050)

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.

Key Buy:

Molly Goddard Camilla Shirred Taffeta Midi Dress (£1300)

Model and yoga teacher Lou Kenny once told us all about how to dress in your 50s, and it’s something you will want to read. Her classic, effortless style and holistic lifestyle make her one to bookmark, no matter what generation you’re part of.

Key Buy:

Arket Relaxed Poplin Shirt (£55)

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.

Key Buy:

Saint Laurent Square-Frame Acetate Sunglasses (£270)

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:

Zara Tailored Double-Breasted Blazer (£60)

Whether she realises it or not, Meghan Markle‘s mother, Doria Ragland, was jettisoned to mother-of-the-bride outfit icon recently. 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.

Key Buy:

Lisa Marie Fernandez Delfi Belted Silk-Chiffon Midi Dress (£198)

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 couture fashion fanatic and a trailblazing trendsetter, wearing all of the latest collections and wildest pieces first. We bow down.

Key Buy:

Proenza Schouler White Label Snake-Effect Faux Leather Straight-Leg Pants (£360)

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 too.

Kalita Clemence Gathered Silk-Habotai Maxi Dress (£825)

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.

Bottega Veneta Ruffled Crepe Blouse (£750)

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.

The Vampire’s Wife The Falconetti Ruffled Silk-Blend Velvet Dress (£1200)

No, Jennifer Lopez does not look like she’s 50. 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.

Emilia Wickstead Petra Belted Leather-Effect Midi Dress (£405)

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.

Max Mara Teddy Bear Icon Camel Hair and Silk-Blend Coat (£1980)

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

Next up, the biggest spring/summer 2021 fashion trends to know.

This article originally appeared on Who What Wear

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