This article was last updated on April 16, 2022
Queen Hatshepsut — Queen Hatshepsut of Egypt took ruling as pharoah to a new level. Donning traditional Egyptian king garb (yep, that includes the uraeus, a traditional false beard, as well as a shendyt kilt and khat head cloth) and adopting a male version of her name, Queen — or shall we say, Pharoah — Hatshepsu went to grand lengths to legitimize her reign. Just check out that falsie!
Queen Elizabeth I — With a taste for over-the-top jewels, exaggerated shapes, and if-you’ve-got-it-flaunt-it pieces, Queen Elizabeth I changed the course of both women’s and men’s fashion, bringing higher ruffs, decorated bodices, and wider skirts and sleeves into fashion. Her bodacious fashions were often done with strategy in mind: Powerful statesmen and nobles from other nations had to be seduced by her as well as fear her power, so her “man-repelling” ensembles were meant to repel most while attracting only those who were worthy of her attention. Talk about a statement outfit!
Amelia Bloomer — While the other ladies were choking themselves with girdles, bodices, and corsets, Amelia Bloomer championed looser-fitting clothing and a new silhouette that involved flowing tops, short skirts, and ballooning pants. Later on in the 20th century, famed costumer and designer Paul Poiret made bloomers a high-fashion staple.
Coco Chanel — With her nearly all-black wardrobe, penchant for baggy silhouettes, pants, traditional dockworker design elements, and tanning, Gabrielle Chanel was definitely an iconoclast against the backdrop of a fit-and-formed, ultra-feminine era. Coco bent all the rules, and began a revolution in womenswear — one that lives on to this day.
Elsa Schiaparelli — In an age of black and white, Elsa Schiaparelli brought color, Surrealist whimsy, and humor into the fashion scene. In hues like Shocking Pink, Schiap’s wares were definitely not for weak, but rather, the lion-hearted.
Rhoda Morgenstern — Mary Tyler Moore may have been the star (at first), but it was her friend, Rhoda, who shone most brightly in our eyes. Master print-mixer, lover of headscarves, and champion of the boho-gone-corporate look, Rhoda taught us that bravery in the office (in both our outfits and our work) can go a long way.
Barbra Streisand in The Way We Were — The curly-haired, bombastic counterpart to the era’s Ali MacGraw standard, Katie Morosky (played by Barbra Streisand) is the fiery, “complicated” girlfriend of straight-shooter Hubbell Gardner. With her business-only attire and elegant ’70s separates, Babs showed us that there was nothing “cute” about being an independent woman. And being the “lovely” woman certainly didn’t have to be the standard.
Annie Hall — Diane Keaton portrayed smart-mouthed Annie Hall in Woody Allen’s ’77 movie of the same name, and showed how bowler hats, three-piece suits, and wide-leg trousers could be just as seductive as a slinky LBD (if not more so). Besides influencing scores of modern-day collections, Annie Hall set the standard for menswear-as-womenswear — and all the ladies who treat blazers as a go-to know who to thank!
Vivienne Westwood — Punk was a fringe, men’s-only movement when it began, but Vivienne Westwood helped bring studs and spikes into the mainstream womenswear market. With her trademark carrot-orange hair, inky-red lips, and Victorian-gone-Vice regalia, Vivienne helped bring skulls, BDSM gear, and lost-and-found items (like toilet chains and dog collars) into high-fashion so gorgeous, not even the most buttoned-up women could resist.
Grace Jones — With her androgynous hairstyle, bodybuilder physique, and from-the-future style, Grace Jones was the anti-diva in a sea of powerful, ’80s entertainers. Dressing in angled menswear suits, spangly leotards, and loads of glitter, Grace Jones built an aesthetic that was genderless, fearless, and completely inimitable (though many have tried!).
Helena Bonham Carter — Walking the red carpet is a big deal for celebrities, and we find it so inspiring that Helena Bonham Carter really just doesn’t give a flying F. Notoriously blasé about fashion and red-carpet affairs, she’s been known to wear mismatched shoes, prom dresses, and Beetlejuice hair in lieu of current-season haute couture… and we wouldn’t have it any other way.
Ghost World‘s Enid and Rebecca — In Docs, cat-eye glasses, ’50s waitress uniforms, and hair bows,Ghost World‘s Enid and Rebecca embodied the f-off disenchantment that was acutely felt by so many suburban teens in the ’90s. And they did it in Riot Grrrl-appropriate zebra stripes, feathered headgear, and ringer tees.
Carrie Bradshaw — While Carrie’s professional life revolved around men, her main obsession was fashion. Despite the multitudes of dudes she dated, she never let a single one come between her and her attention-grabbing outfits (remember her wearing a fur coat to a baseball game or those gigantic silk flowers?). We even wager that she probably spent more time at Barneys than in Big’s arms.
Sofia Coppola — Sofia Coppola may just be ballet flats’ biggest champion, choosing them over stilettos time and time again on the red carpet. Despite what the best red carpet experts will tell you about the magical leg-lengthening, body-slimming effects of a vertiginous heel, Sofia refuses to convert. Flats, FTW!
Lady Gaga — Lady Gaga and her fleet of “Little Monsters” have made standing out and looking weird supremely cool, and Gaga’s taken every opportunity to go for the strange, appearing at the 2010 MTV VMAs in a dress made of meat and forgoing pants, every opportunity she gets. It’s not sex appeal she’s after, it’s shock appeal.
Leandra Medine — Though the concept’s been around forever, Leandra’s the one who’s responsible for coining and popularizing “Man Repelling” as a style. With her magpie philosophy toward accessories, mismatched tastes, and bold silhouettes, Leandra’s one of our favorite people because she literally wears her personality on her sleeve.
Illustrations by Naomi Abel
Research by Michelle King
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