UNIFORM | Levi's Corduroys

Levi's advertisement from the September 1964 issue of Playboy via Vintage Ads and Stuff.

"Never, under any circumstances, let a girl borrow your White Levi's of Cone Corduroy. If she says she's going to a costume party and wants to go dressed as Huckleberry Finn, turn a deaf ear or lend her an old shirt. But don't part with your Levi's. Girls find long, lean, well-tailored Levi's irresistible. Especially in extra heavyweight corduroy. And if yours happen to be softened with age, so they look and feel like old leather, you're a goner."

MOMENT | Jessica Miller as Jane Birkin

Photos of model Jessica Miller posing as Jane Birkin for the March 2007 issue of Vogue Paris by Peter Lindbergh. Found via Milk.

NOISE | Warpaint

Photo via The Spielster

GEAR | Mirrored Sunglasses

Photo by Henry Groskinsky, 1977.

UNIFORM | Father's Oxford

Photo via Mister Mort, 2009.

"She wears her father's oxford shirt with cut off vintage Levi's cords and carries a vintage L.L. Bean tote." —Mister Mort

MOMENT | Ad Hoc White House Car Wash

First daughter Susan Ford washing her car outside The White House in 1975 (via The Ford Library).

SCENE | Yearling Row

Ronald and Nancy Reagan at their Malibu Canyon Ranch “Yearling Row” in the 1950s.

"And so when Ronnie bought Yearling Row, his first ranch in Malibu, I went out and took it upon myself to paint his picket fences. That was no small job: It was a 360-acre ranch! I painted into the sunset, until there wasn't a single streak of light left in the sky. At the end of each day, I'd take off my blue jeans and they'd be so caked with paint that they'd almost stand up on their own. My skin would be in similar condition. One day my makeup man at Metro said to me: 'I have to tell you, Nancy, this is a first: I've never had to make up an actress at Metro and first remove paint from her face.'"—Nancy Reagan in an excerpt from I Love You, Ronnie: The Letters of Ronald Reagan to Nancy Reagan

I want to note that Nancy Reagan really wasn't a tomboy by any stretch, but in the context of their ranch life, I think the First Lady is owed some credit for convincingly, as a good actress would, playing the role. Happy Presidents Day. —LGM

SCREEN | Love Story

Film still of Ali MacGraw and Ryan O'Neal in Love Story via screenshot.

Oliver Barrett IV: Well what makes you so smart?
Jennifer Cavalieri: I wouldn't go out for coffee with you that's what.
Oliver Barrett IV: Well what if I wasn't even gonna ask you to go out for coffee with me?
Jennifer Cavalieri: Well that's what makes you stupid.

I had been thinking about this movie for a while, I can't believe in 1970 MacGraw was 31 playing a college student. Flawless. Thank you to reader Josée Wang for reminding me about Love Story!

ICON | Elle MacPherson

photo via RolexMagazine.com

"The young Australian was, by her own confession, a tomboy who preferred climbing trees to playing with dolls." —Hello! Magazine

ICON | Chan Marshall

Photo by Erich Schlegel for The New York Times.

"She wore a faded green shirt, bluejeans, and black Christian Louboutin heels." —Sasha Frere-Jones, The New Yorker.

As I collect photos for the book, I keep coming back to one person again and again: Chan Marshall. She embodies the style, the spirit and the soul.

SCENE | WWII furlough

Photo from the LIFE archives.

UNIFORM | Elden Slip-On Oxfords

Photo via That Kind of Woman

Got a have a pair.

SCREEN | Mogambo

Photo of Ava Gardner in a scene from the film Mogambo by Peter Stackpole, 1953.

SCREEN | Two-Lane Blacktop

Film still of Dennis Wilson, Laurie Bird and James Taylor, 1971 via The Selvedge Yard.

ICON | Katharine Ross

Photo of Katharine Ross with Robert Redford and Paul Newman on the set of Butch Cassidy and The Sundance Kid, 1969 via allstarpics.

ICON | Jane Goodall

Photo of Goodall by Hugo Van Lawick/National Geographic, 1974.

"I was never, ever told I couldn't do something because I was a girl." —Jane Goodall

ICON | Emmanuelle Alt

Photos of French Vogue's new editor-in-chief via Jak & Jil.

ICON | Gene Tierney

Photo of Gene Tierney and friend Maturin Waldo lighting her cigarette behind the stables of the Fairfield County Hunt Club in Westport, CT. by Hart Preston, 1940.

SCREEN | The Misfits

Marylin Monroe on the set of The Misfits, 1960 (via MPTV images).

SCENE | British Columbia

Photos of William and Brenda Holden on vacation in Canada by Allan Grant, 1949.

UNIFORM | Bass Weejuns

Photo of Grace Kelly wearing Bass Weejuns via Film Noir Buff.

G.H. Bass & Co. has been making this simple and uncluttered tomboy staple since 1936.

*Thanks to the anonymous Tomboy reader for the great suggestion.

SCENE | Muzzle Loaders Club

Photo by Wallace Kirkland, 1948.

GEAR | Rolex Oyster

Photos of Mercedes Gleitze, the first British woman to swim the Channel, by E. Bacon, 1927; image of 1930 Rolex Oyster catalog via Time & Gems.

"Miss Mercedes Gleitze carried an 'Oyster' throughout her recent Channel swim. More than ten hours of submersion under the most trying conditions failed to harm its perfect timekeeping. No moisture had penetrated and not the slightest corrosion or condensation was revealed in the subsequent examination of the watch." —London Daily Mail front page announcement, November 23, 1927.

SCENE | Porsche Time Trials

Photo of Mrs. Bickerson behind the wheel in 1960, via 12 paws and frogs.

ICON | Joanna Shimkus

Film still via Nostalgie Zoe.

Love those jeans.

ICON | Rose Kennedy

Photos of Rose Kennedy and granddaughters Caroline and Courtney by Leonard McCombe, 1970.

"Better broken bones than broken spirit." —Rose Kennedy

SCENE | Sweet Briar College Lacrosse

Photo of Sweet Briar College lacrosse practice by Peter Stackpole, 1951.

After a brief grace period, when she would be called a tomboy and allowed to play second base, a girl has traditionally been subjected to heavy social pressure to withdraw from athletics. "Sports was the laboratory where they turned boys into men," says Penn State Psychologist Dr. Dorothy Harris. "As for girls, they were supposed to stand out in the hall, quaking in their tennis shoes. The penalty for daring to take part was to be labeled unfeminine, a social deviant. What is considered healthy psychological development in a man—aggressiveness, independence, ambition, courage, competitiveness—was viewed as unhealthy in a woman. Yet it is precisely those qualities that are found in every athlete, male or female. Whatever it is that works for little boys also works for little girls." —an excerpt from Comes The Revolution, Time Magazine, June 26, 1978.

SCENE | Pheasant Shoot

Photo by George Silk, 1950.

"Women never look so well as when one comes in wet and dirty from hunting." -Robert Smith Surtees