How to Dress Like Jack Kerouac

Guest blogger Roxana Altamirano, the genius behind Nerd Boyfriend, shows you how to get the author's look.

ca. 1957, Tangier, Morocco --- Jack Kerouac holding William S. Burroughs' cat in Villa Muneria, Tangier in 1957; text written by Allen Ginsberg. --- Image by © Allen Ginsberg/CORBIS

Credit: Corbis

Jack Kerouac was a groundbreaking nontraditional writer with a very traditional, all-American personal style. His fashion choices paid tribute to the drifters, the working men, and his brief experience in the armed forces.

In an early photo (below), Kerouac wears WWII-style, deep-pocketed, pleated khakis with a solid white tee. A decade later, Kerouac swapped the khakis for loose selvedge wash jeans, and completed the look with a newsboy cap, khaki jacket, and rugged work boots (above).


Credit: Corbis

Carhartt Twill Jacket in Khaki.

Naked & Famous Heritage Selvedge Wash Jeans at Karmaloop.

Rugged Red Wing Boots at J.Crew.

Stetson Bruce Newsboy Hat at HatsintheBelfry.


Credit: Corbis

Vintage-Inspired Khakis from Bills Khakis.

Velva Sheen domestic cotton crew neck tee in white at Hickorees.

About the Author: Even for the most skilled dressers, assembling a killer outfit sometimes requires a little more inspiration than the average online shopping experience provides. Enter Roxana Altamirano, the genius behind Nerd Boyfriend, the style blog that offers step-by-step instructions for re-creating ensembles worn by icons ranging from Michael Caine to Tom Hanks (see full list here). Now she's guest blogging on every week. Have a hero you want to see featured? Leave a note in the comments and we'll see what we can do.

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