ertain fashion items hold strong cultural value because they are instantly connected to a famous wearer. I can’t even look at a basket bag without thinking of Jane Birkin. Some of these items—like Paris Hilton’s Juicy Couture tracksuits—were left behind in the time when they reached their peak. Others manage to transcend decades and maintain a timeless quality because they work outside of the trend cycle. These classic items are subtly refined, and the wearers that made them famous did so in an understated yet powerful way. This form of elegance makes these pieces iconic in the truest sense of the word, and we still see their legacy continue today.
It’s been 62 years since Audrey Hepburn danced across our screens in Funny Face wearing a pair of cropped black trousers, and yet her outfit is still something you’ll likely see someone wearing on your commute to work.
No matter the season, trend or year, like many classic items, these lovely, reliable pieces will remain in your wardrobe forever. Each time you put them on, you will imbue your look with something tangibly classy. It’s like a direct boost of confidence from the women who made them legendary.
From the pieces themselves to the fabulous women who made them famous, keep scrolling to see and shop the most iconic, elegant clothing and accessories that will simply never go out of style.WHITE BUTTON-DOWN SHIRT
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Style Notes: From Carolyn Bessette Kennedy to Sharon Stone at the 1998 Oscars, a slightly oversize white button-down was a low-key rebellious cocktail piece in the ’90s. Now, with a bit of red lipstick, it is instantly an elegant win.
Everlane Shrunken Cotton Shirt ($55)BIG SUNGLASSES
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Style Notes: While tiny sunglasses have their moment every few decades, oversize sunnies are forever chic thanks to their number one fan, Jackie O.
Celine Oversized Acetate Sunglasses ($430)CROPPED BLACK TROUSERS
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Style Notes: This might have been a “casual” look in the film Funny Face, but in the world of legendary style moments, Audrey Hepburn’s black cigarette trousers became synonymous with forever cool.
H&M+ Dress Pants ($18)STATEMENT EARRINGS
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Style Notes: Through the ’60s, statement earrings loved by stars like Diana Ross and Edie Sedgwick. But it’s Nina Simone at the piano (wearing little else than her oversized earrings) that is the epitome of elegance in my mind.
Isabel Marant Hammered Disc Drop Earrings ($385)SUITING
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Style Notes: Katharine Hepburn, Diane Keaton, Bianca Jagger, Julia Roberts, and now Jeanne Damas are just a few of the awesome women who have famously owned wearing men’s suit jackets.
Max Mara Oxford Blazer ($1690)TURTLENECK
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Style Notes: From Ali McGraw in Love Story to Sade’s signature look, the understated power of a basic turtleneck is mysterious and always works.
J.Crew Perfect-Fit Turtleneck ($37)SATIN SLIP DRESS
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Style Notes: In one of her most iconic post-divorce outfits, Princess Diana pairs a simple lingerie-esque satin dress with a Dior Lady bag and pearl-chain necklace.
Topshop Lace Satin Slip Dress ($75)HAIR BOW
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Style Notes: Popular among ’60s French film stars like Catherine Deneuve in The Umbrellas of Cherbourg and Brigitte Bardot, a hair ribbon now adds a touch of je ne sais quois to any outfit.
Namjosh Velvet Bow Pony Holder ($25)TOP-HANDLE BAG
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Style Notes: Like the Birkin, when Grace Kelly debuted her royal engagement holding her Hermès Kelly, the bag world was never the same.
Saint Laurent Manhattan Medium Leather Tote Bag ($1735)WHITE JACKET
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Style Notes: I’m not sure if they were doing it to keep looking fresh, but ’90s supermodels like Naomi Campbell, Linda Evangelista, and Christy Turlington often wore white rather than black. Chic.
Mansur Gavriel Oversized Linen Coat ($850)SHEER TIGHTS
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Style Notes: When it comes to hosiery, go sheer. It instantly harkens to the late glam of the late ’80s, and they go with anything from a vintage cocktail dress to a suit jacket.
Heist The Thirty Tights ($36)CHAIN NECKLACES
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Style Notes: As an essential part of Coco Chanel’s signature personal style, layered chain necklaces carry on their elegant legacy through many fashion muses—including Loulou de la Falaise and Tina Chow.
Vintage Chanel CC Necklace ($784)
