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).
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.
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 Details.com every week. Have a hero you want to see featured? Leave a note in the comments and we'll see what we can do.