Jack Kerouac: Style Icon of the Beat Generation

The Effortless Cool of Writer Jack Kerouac: Just Don't think Black and Berets...

              

               Imagine yourself hunched over a typewriter in your apartment, tapping away on a 10-foot-long scroll of paper, going through endless notes you've written in an attempt to finally get your damn thoughts out. As prolific as he was, that was Kerouac's way of working. And, although he was originally met with criticism and had trouble finding a publisher, he would eventually become the voice of a generation — the beat generation.

He published often, but On The Road still stands out. Sections on drug use, homosexuality, and various taboo subjects (at the time, at least) made it that much harder for Kerouac to get the work published once he finished it in 1951; it didn't help that the manuscript was one continuous paragraph on that very long sheet roll. But once it eventually hit shelves in 1957, the author became an instant celebrity — something he never wanted and, reportedly, didn’t really enjoy. For one, people started paying a lot of his attention to his casually elegant style, a way of getting dressed that still feels modern today...

Get the look: The "Kerouac" brand of nonchalant cool 

Jack Kerouac is one of the most well-known male writers of all time, and for good reason. Kerouac’s novels embody the mystique of a nomadic lifestyle, and sparked a romanticism for the road in countless generations of American men. Perhaps the most intriguing thing about Kerouac’s writing is that his lifestyle was very much in line with what he wrote about, with little to no pretension or fabrication injected into the final product. Kerouac exuded cool, and certainly dressed the part. For men who are looking to embrace the philosophy of the open road, it’s important to have an idea as of how to dress. Kerouac’s style was effortlessly cool, and any fashion-forward guy can emulate it with success without having to try too hard. The following are just a few tips to help you dress like Jack Kerouac,
Caution: Achieving this type of Beat Generation cool may cause you to suddenly take up chain smoking, buy a vintage typewriter or develop a sudden Benzedrine addiction...in some cases worship of jazz music via the 1950's can appear.  

 Kerouac certainly found himself in and out of creative circles, the hippie-dippy floral prints and bright colors that are so often associated with this era were the exact opposite of his M.O. In fact, Kerouac had perfected "homeless chic" long before the Olsen twins. Often dressing in layers of long jackets, untucked shirts, scuffed jeans, perfectly unperfected lose ties, blazers and various accessories such as hats, classic pea coats and that ever present cigarette. He had a way of always being slightly unkempt, disheveled and road weary, yet this effortless "just woke up and put together to catch a train to Mexico City" look exudes the kind of cool that even cool people covet: he literally wore whatever he had handy. He didn't care about how cool he looked, or how he dressed...he was too busy being cool!

Despite the lack of trying, Kerouac's ragged, simple layers came across as both unique, bohemian and attractive in manner. Jack's novels wrote of adventures and elaborately stylish "Beat" scenes in places like San Francisco; but the sleek, artful creatures clad in all black depicted in his literature had nothing to do with the Kerouac brand of style.

Kerouac: Embodying the Modern men's style of today

Kerouac: Fit for Gap or JCrew ad? Flannel and Oxford shirts: 

The slightly wrinkled, untucked, half buttoned brand of button down you see on all the men's displays at the mall (those of course were made to look that way) was a trademark Kerouac piece.
Khakis and Layers:
Kerouac was very often seen wearing khaki slacks; his go-to pants. The writer preferred slacks not only because they were comfortable, but could easily be paired with a variety of different ensemble elements. For example, the right pair of slacks looks fantastic with Oxfords, Polos and flannels, not to mention a great deal of other shirt styles.
Embrace the Bomber Jacket
It’s true that Kerouac was most often seen wearing flannel shirts and denim work shirts, both of which served as crucial pieces that made his look what it was. When the temperatures started falling, however, Jack Kerouac preferred to throw on a bomber jacket, which not only helped to keep the cold at bay but added a whole new element to his look. A lot of guys are hesitant about trying to wear bomber jackets, and for good reason; they often don’t look right when worn by the wrong person. That said, the bomber jacket will fit in nicely with just about every other element of Kerouac’s style, and shouldn’t be overlooked. For something slightly different, consider pairing an olive-green bomber jacket with black slacks; an urban look that’s difficult to beat on a fall day.