ICON | Kathy Kohner

Photos by Allan Grant, 1957

"Some people have Alcoholics Anonymous, Starbucks, church...I had Malibu."—Kathy Kohner (the real-life inspiration for Gidget who started surfing at the age of 15, sometimes trading her peanut butter and radish sandwiches for chances to ride)

SCENE | Sun Valley, Idaho

photos by George Silk, 1958

SCENE | Fall Football

Photo by John Loomis, 1971

"Football is all very well as a game for rough girls, but is hardly suitable for delicate boys." —Oscar Wilde

ICON | Princess Cecile of Bourbon-Parma

Photo of Princess Cecile of Bourbon-Parma after flying her glider over central France by Loomis Dean, 1959

"Princess Cecile holds a pilot's lisence and as a daughter of Prince Xavier of Bourbon-Parma, her interests include social work, agriculture, philosophy, folklore, hunting and a variety of sports." —LIFE, Feb. 8, 1960.

UNIFORM | Misfits t-shirt

Chloe Sevigny on a skateboard by Moe Jackson, via Happenstance.

"There aren't that many girls who can pull off wearing a Misfits shirt while riding a skateboard and pull off wearing a Proenza Schouler dress at the Met Ball. I love how Chloe Sevigny can effortlessly do both." —Haydee Sentianin

CONTEMPORARY | Freja Beha Erichsen

photos by Cass Bird for Dossier

"The intrigue of androgyny has been a style-staple throughout the twentieth century— think of Saint Laurent's Smokings, Chanel and her Matelot jerseys—today, that whole 'boy-girl' thing retains its undeniable allure. Illustrating this point perfectly is fashion's favorite 21st century tomboy, Freja Beha Erichsen." —unknown source

ICON | Claudine Longet

photo of Claudine Longet in Japan via the Hulton Archive/Getty Images, 1968.

"In Blake Edwards' 1968 film The Party French yé-yé girl and actress of unfortunate notoriety Claudine Longet plays Peter Sellers' demure love interest, Michele Monet. Starting out as just another winsome waif in a mini-dress, Michele dives into the pool to save a drowning man, changes into a pair of teenage boy's blue denim jeans, a loose-fitting, collarless, heather-gray Love thy neighbor sweatshirt, and instantly has sexy, carefree wet hair. Her social restraints and shoes have been tossed aside, and riding a baby elephant victoriously, she is the life of The Party." —Sarah Maher, Refinery29

ICON | Joan Baez

photo by Ralph Crane, 1962

“I generally like to get to the point.” —Joan Baez

SCENE | Santa Barbara Sports Car Racing

photo by Allan Grant, 1960

SCENE | Aspen in the 70s

photo of Mary Duffey in Aspen by John Dominins, 1971

"For me, skiing is a physical necessity. I have a need for risk." —Jean-Marie Messier

SCENE | Colby College Mountain Day

photo by Yale Joel, 1950

ICON | Jacqueline Bisset

photo of Bisset in Malibu, 1967 courtesy of Mirrorpix/The Everett Collection

"A mode of conduct, a standard of courage, discipline, fortitude and integrity can do a great deal to make a woman beautiful." —Jacqueline Bisset

SCENE | The Snake River

photo by Alfred Eisenstaedt

"By the time I had turned thirty, I'd realized two important things. One, I had to fish. Two, I had to work for a living."—Mallory Burton

CONTEMPORARY | Lissie Maurus

photo by Alan Wild

"I generally do wear jeans and a t-shirt. I don't wear a ton of makeup. I show up on stage and I sweat."—Lissie Maurus

ICON | Ethel Skakel Kennedy

photo from LOOK Magazine, 1968

"Ethel Skakel was a bubbly, headstrong young woman who loved to tease and who wanted, as much as any Kennedy, to win. She greeted everyone, "Hiya kid," and distracted the nuns at Manhattanville with her gags and practical jokes. A tomboy, she had been indifferent to boys. Working with Bobby in East Cambridge that June, however, she developed a crush. Bobby did not reciprocate. He was more romantically inclined towards Pat Skakel, Ethel's older sister. Ethel was determined to win him anyway...More athletic and outgoing than Pat, she "turned the tide," Jean Smith later reported. By the time Bobby was at law school, he was regularly flying up to visit Ethel on the weekends. At Hyannis house parties, Ethel, sporty and joshing and ebullient, became difficult to distinguish from the Kennedy sisters." —Evan Thomas, author of Robert Kennedy: His Life

UNIFORM | Brooks Brothers

photo by Nina Leen, 1954

"Although Brooks Brothers is generally identified with impeccably conservative male plumage, the staid New York store has recently become a shopping haunt for sophisticated women. This trend was started when the store opened a counter, placed discreetly at the rear of the main floor, where tweedy young women from college or the suburbs could buy the Brooks Brothers man's shirt many of them had begun wearing. Given this opening, more and more women have encroached upon the whole store, greedily discovering other items of male apparel that they can take over for themselves." —LIFE magazine, 1954

ICON | Peggy Lipton

photo by Vernon Merritt Iii, 1970

"Elvis was a good kisser, but that was about it." —Peggy Lipton

ICON | Carole Lombard

photo of Actress Carol Lombard wearing sunglasses for skeet shooting at gun club by Alfred Eisenstaedt, 1938

"I can’t imagine a duller fate than being the best dressed woman in reality. When I want to do something I don’t pause to contemplate whether I’m exquisitely gowned. I want to live, not pose!” —Carole Lombard

SCENE | The Rodeo

photo by Martha Holmes, 1948

"The way to avoid housework is to live outside." —Sandra Blacksmith, 1900