Fashion Icons Over 50

The fashion industry has the tendency to abandon women once they hit a certain age. After slavishly following the trends throughout our twenties, thirties and forties, we become a largely ignored minority once we hit fifty.

As it stands, high fashion is available to younger women at high street prices, but older women – who are probably in the best position to be spending their savings on clothes – miss out. The glossies, but for the rare and obligatory ‘Age Issue’, stop telling you what you should and should not wear once you hit a certain number.

This shouldn’t be regarded as a bad thing, however. As Alison Lurie would tell you, breaking free from the fashions is a strangely liberating process. As you stop subscribing to trends, you stop dressing to please others and start dressing to please yourself.

When I grow up, I want to be a bag-lady eccentric, moneyed old lady – and I look to these fabulous, over-fifty women for inspiration. These women – a few of whom are regulars on Ari Seth Cohen’s Advanced Style and were recently the subject of a Channel 4 documentary – are a part of a growing demographic. They don’t see age as something to hide from, but something to embrace. And with style sensibilities that fall closer to the ‘eccentric’ than the ‘sensible’ side of the spectrum, they’re head-to-toe living proof that dressing to stand out is not solely the prerogative of the young. When fashion passes, style remains …


Joyce Carpati, 81 

Who is she? A former opera singer, friend and former colleague of Cosmopolitan’s founder, Helen Gurley Brown, cover star of Advanced Style’s new colouring book and self-described good conversationalist. Here she is breaking into song on the streets of New York.

When asked to share her best advice, Carpati told online lifestyle magazine, The News: “Be optimistic, join in, don’t be negative, be positive in everything that you can and it will come your way and work out.” 


Jil Sander, 69 

Who is she? The designer and inventor of minimalist chic.

“We look our best in subdued colours, sophisticated cuts, and a general air of sleek understatement,” Sander told GQ when quizzed on her minimalist secrets.  


Ilona Royce Smithkin, 93 

Who is she? A painter, educator and singer and with a penchant for two-inch, handmade, red eyelashes. The 91 year old recently modelled eyewear for Karen Walker.

"Never compare yourself," the vibrant Smithkin advised Advanced Style, “I feel beautiful inside and that’s beautiful enough for me.” 


Debra Rapoport, 68 

Who is she? A thrift-shopping artist who lives by the mantra "look good, feel good, feel good, look good”. Her favourite accessories include her DIY bracelets made from toilet paper rolls.

“I know too many women who, after 50, walk around with hoodies and sweat clothes," Rapoport told Glamour. Her advice? "Pull yourself together! Find your good assets and flaunt them and support them. I get a lot of emails from 25-year-olds saying, ‘I can’t find my style, I don’t like myself, I don’t know what to wear.’ It’s so sad at that age to not even explore and try and play. It’s all about play.” 


Iris Apfel, 92 

Who is she? An interior designer and businesswoman cum style icon slash the world’s oldest it-girl.

“No amount of money can buy you style," Apfel has said. "If someone says, ‘Buy this – you’ll be stylish’, you won’t be stylish because you won’t be you. You have to learn to learn who you are first and that’s painful … I don’t try to intellectualise about it because it tightens you up. I think you have to be loose as a goose.” 


Carine Roitfeld, 59

Who is she? The former Vogue Paris editrix and founder and current editor-in-chief of CR Fashion Book, known for her signature scruffy-meets-sexy look.

Roitfeld's secret to style through the ages? “There are too many 50 year olds dressing as 20 year olds. You have to look every five years at your wardrobe and say: ‘If it okay to wear this with my legs? Is it okay to wear sleeveless with my arms?’ Then you have to cull. It’s not nice but you have to do it.” 


Arianna Huffington, 63 

Who is she? The founder of The Huffington Post.

“I think power dressing can be anything," Huffington said in an interview with Elle. "It doesn’t have to be a suit. That’s very ‘80s … My aspiration is to end my life entirely in flats. I feel so much more comfortable if I can walk around without being in pain.” 


Diane von Furstenberg, 66 

Who is she? The designer of the iconic wrap dress, who once posed for Andy Warhol and was two-times the cover girl for his Interview magazine, says that if there is one rule for fashion, it's the same rule as everything else in life:

 “Don’t go against yourself, don’t go against your own nature. It’s only going to show.”


Lee Radziwill, 80

Who is she? A former princess, interior designer, society gal and younger sister of Jackie Onassis. Here she is in conversation with Sofia Coppola speaking about going on tour with the Rolling Stones and Truman Capote. Radziwill shares tidbits of life advice via the Twitter hashtag #LifeLessonsWithLee.

"I’m nobody’s kid sister,” she says defiantly. 


Carmen Dell’Orefice, 82 


Who is she? The world’s oldest working model, who shot her first Vogue cover when she was 15.


Dell'Orefice's describes her individual style as: “Comfort first, affordability second, event third, I have a collection of things I’ve liked since 1945 that fit any occasion.”