"The Prince of Wales is my Godfather. A wonderful one. But as a tomboy it was hard to forgive being asked to wear that frilly dress as a bridesmaid to him and Lady Diana."—India Hicks
photos by The Sartorialst and Peter Miszuk
"My mother has very inspiring style and when I was young, she always managed to look incredibly chic by being creative with few resources. And Lauren Hutton is an fashion icon for me as well. Both are examples of natural, sexy, strong women who really look stunning in a men’s shirt." —Jessica de Ruiter
photo from Wild World of Skateboarding
"I wanted to be better at something than my older brother—he was a star swimmer and water polo player. He couldn't even do a 360 on a skateboard."—Cynthia Whitehead
photo from tout le cine
Mike Wallace: What moved you to try so hard to get [into acting]?
Jean Seberg: When I was twelve, I saw Brando.
An excerpt from The Mike Wallace Interview, aired January 4, 1958.
photo by Michael Thompson for W Magazine
"My dad took me to all the best rock and punk shows when I was growing up."—Winona Ryder
photo by FlyingTelevision
"I was a tomboy [as a teenager] and went through a lot of different phases. When you shave your head and pierce your nose during your junior year in high school, that’ll do it." —Chloë Sevigny
photo by K-Swiss
"Alexandra dresses like a laid-back tomboy, in big shirts and tight pants, a la Keith [Richards], whose trousers [she wears] around the house. She is into casual chic, and dresses down pretty frocks with skateboard sneakers."—Plum Sykes, Vogue
"In an era in which every teen star has a stylist and a bland pop record, 19-year-old Kristen Stewart is the tough-minded, no-frills anomaly."
—Evgenia Peretz, Vanity Fair
"No boy could be my friend until I had beaten him in a race, and no girl if she refused to climb trees, leap fences and be a tomboy." —Louisa May Alcott
Photo of Michael Jackson and Tatum O'Neal in 1979 by Michael Ochs
"Tatum has a spunky personality and marvelous husky voice." —Peter Bogdanovich
"I'm like a 13 or 14-year-old boy who loves fun music and hot chicks and sport, and I like empowerment and women who are capable and humorous. I think I am extremely androgynous."—Drew Barrymore
photo by Sarah Meadows
"I'm a straight gay. I have political and emotional affiliations to one world, as well as love for it, while biology dictates operations in the other. I'll leave it up to you to surmise which is which. I consider myself to be somewhat of a blank slate, and your interpretation of my orientation tells me more about who you are than tells you about who I am." —Claire L. Evans
"Wait, am I dressing like a 14-year-old boy, or are all 14-year-old boys dressing like me?”—Sarah Silverman
"It's a good group of guys to hang out with...we play games, we watch science shows, play mini golf, and shoot machine guns."—Alison Mosshart
photo by Margaret Bourke-White from the LIFE archives
"Her hands, with their short, unpainted nails, are the used hands of a busy, creative person, but the enormous emerald solitaire looks perfectly at home guarding her wedding band. She wears other emeralds so casually that she might have been born with them."—Virginia Lee Warren (an excerpt from the September 1, 1964 New York Times article "Woman Who Led an Office Revolution Rules an Empire of Modern Design")
"She’s much more than just the torch singer leaning against the ballad with a lone spotlight on her. In a past life, she was a shouty battle of the bands teen queen in a Calgary punk band. She’s stubborn and meticulous about things like the EQ level on the stereo and her long honed guitar tone. She’s been placed in the role of the most unlikely fashion icon, but mostly she’s a tomboy who doesn’t really do make-up." —A&C Records
"Alice was known to slide miniature bottles of whiskey in her elbow-length gloves and smuggle them into teetotaling houses so she could present them to her male dinner partners. In her purse, she could be counted on to carry four essentials: cigarettes, a fertility image (no doubt sanctioned by the R.S.C.), her green snake named Emily Spinach (after her thin aunt), and a copy of the Constitution." —Stacy A. Cordery (an excerpt from Alice: Alice Roosevelt Longworth, from White House Princess to Washington Power Broker)
Heaven Can Wait by Charlotte Gainsbourg + Beck
Mr. Alan knows how to dress a tomboy.
Super Basic sunglasses ($117); Boyfriend pullover ($158); Keds ikat slip ons ($68); Fidelity waxed scooter jacket ($210); Levi's 1960 Black Tab shorts ($195); Sunshine + Shadow wrapped belt ($198); Filson original briefcase ($218); Selvedge scarf ($98).
Annie Oakley by Andy Warhol, 1986
"My mother was perfectly horrified when I began shooting and tried to keep me in school, but I would run away and go quail shooting in the woods or trim my dresses with wreaths of wildflowers."—Annie Oakley
"Raised by her mother and stepfather (she never knew her natural father, who died in his mid-30s) in the deep south, [Hutton] was indeed a tomboy who explored the swamp behind her house with the regularity of a Mark Twain character." —Alex Simon, Venice Magazine
"I was never too interested in high school. I mean, I never went to a dance, I never went out on a date, I never went steady. It became pretty awful for me. Except, of course, I could go see bands, and that was the kick. I used to go to Cleveland just to see any band. So I was in love a lot of the time, but mostly with guys in bands that I had never met. For me, knowing that Brian Jones was out there, and later that Iggy Pop was out there, made it kind of hard for me to get too interested in the guys that were around me. I had, uh, bigger things in mind."—Chrissie Hynde
"The Breakfast Club really bothered me. This is, like, an iconic movie, and the coolest character, Ally Sheedy, goes from being this interesting, quirky girl to being made 'hot' so she can make out with frickin' Emilio Estevez? Give me a break!"—Ellen Page
"When I was a little girl I would watch old black-and-white cowboy movies on television every Saturday morning and afternoon, rain or shine. I would dream of being a cowgirl, of riding the range and roping the steers, of sitting on bales of hay and singing to the strains of guitars at evening campfires."
Talking Heads bass player Tina Weymouth in 1978
"Ex-Velvet Underground member John Cale says Tina was queen because she had that 'Jean Seberg thing going', that short-haired look of the actress who played Joan of Arc for Otto Preminger. The New Wave tomboy who hawked The Herald Tribune in Godard's Breathless. Both Jean Seberg and Tina Weymouth seemed adorably feminine because to paraphrase Seberg's lover Carlos Fuentes, 'to get those two you had to negotiate the twist and turns of androgyny and homoeroticism.'" —David Bowman (an excerpt from This Must Be the Place: the Adventures of Talking Heads in the Twentieth Century)
"She came in and the costume lady on Annie Hall said, 'Tell her not to wear that. She can't wear that. It's so crazy.' And I said, 'Leave her. She's a genius. Let's just leave her alone, let her wear what she wants.'—Woody Allen
"As far as I'm concerned, being any gender is a drag." —Patti Smith
1a. Hanes white v-neck 1b. LnA zipper pocket tee 1c. Chance classic tee 1d. Saint James striped tee.
2a. Classic red bandana 2b. Apolis + Matteo striped linen bandana 2c. Vintage Vera scarf 2d. Hermes scarf.
3a. Jeep CJ-2A 3b. Ford Bronco Roadster 3c. Jeep Grand Wagoneer 3d. Range Rover Classic
4. Hello there.
5a. Vintage British Military Rolex Submariner 5b. Nixon Time Teller P 5c. Timex Weekender 5d. Swatch Original.
6a. Coco Chanel 6b. Isabel Marant 6c. Ralph Lauren 6d. Stella McCartney.
7a. Converse Chuck Taylors 7b. Tretorn T58s 7c. Vans Authentics 7d. Superga Trainers.
8a. Seil Marschall Canoe pack 8b. Herschel Supply Settlement pack 8c. Jansport Heritage pack 8d. Fjallraven Kanken pack.
9a. Yves Saint Laurent "Le Smoking", photo by Helmet Newton 9b. Maison Martin Margiela 9c. Rick Owens 9d. Céline.
10a. Levi's 10b. Current/Elliott 10c. J Brand 10d. Acne.
11a. French Vogue 11b. Foam 11c. Garden & Gun 11d. The Gentlewoman.
12a. Randolph Engineering Aviators 12b. Moscot Lemtosh sunglasses 12c. Ray-Ban Wayfarers 12d. Persol.
13a. Chanel Le Vernis 13b. RGB 13c. Essie 13d. Butter London.
14a. L.L. Bean boots 14b. Quoddy Boots 14c. Red Wing Heritage 14d. White Mountaineering.
15a. Nantucket Rope Bracelet 15b. Tanya Aguiniga Rope Bracelet 15c. Miansai rope bracelet 15d. Missoni woven bracelet.
16a. Photo of Carolyn Bessette Kennedy wearing a classic white shirt by Ron Galella, 1999. 16b. Boy. by Band of Outsiders 16c. Madewell Wayward jean shirt 16d. Aubin & Wells Wellfield shirt.
17a. Army duffle 17b. T. Anthony duffle 17c. Filson Duffle 17d. Swaine Adeney Brigg Safari range luggage.
18a. Gucci drivers 18b. Belgian Shoes 18c. Bass Weejuns 18d. Tod's Gommino loafer.
19a. Fender Telecaster 19b. Gibson Les Paul 19c. Rickenbacker 330 19d. Hofner 500/1 bass.
20a. Billy Kirk No. 109 20b. Apolis Hoofpick belt 20c. Colonel Littleton No. 5 20d. Hermes Etrivière 32.
21a. Wm. J. Mills classic tote 21b. Artifact Bag Co. No. 105 21c. Ernest Alexander tote 21d. Tampico Bags cotton tote.
22a. Helly Hansen rain coat 22b. Grundens rain coat 22c. Patagonia Deep Wading Jacket 22d. Barbour Beadnell.
23a. Bud Heavy 23b. 21st Amendment IPA 23c. Fat Tire 23d. Guinness.