For men, wearing a jean jacket is like shaving with a straight razor: The high degree of difficulty scares away the faint hearted, but those that do it well appreciate the air of nonchalance it affords them, and the stylishly-iconic company they find themselves in.

Lately Mr. West (pictured above…not the prophetic Princeton Prof.) has been seen wearing a vintage Big E Levi’s jacket…. Now, while the bowtie is a bit avant garde for your average lunch meeting at California Pizza Kitchen, we are of the mind that the time is right for every American man to buy the denim jacket he’s always wanted, but wasn’t sure he could pull off.
Men: Appreciate the history of what you’re wearing. The more you know the more comfortable you’ll feel about wearing it, and the more confidently you’ll rock it. You think Kanye knows his jacket is a “Big E”?…. You’re damn right he does..


The earliest denim jackets came to be around the same time as the development of the classic 5 pocket blue jean. They were called “Work Blouses” and were worn more as a heavy weight shirt than as a jacket. The high waisted pant and shorter jacket were favored by cowboys as they were more saddle ready than the high-backed bib overalls worn by their mine-bound blue collar counterparts. The jackets had pleats in the front that were often let out by their cowboy owners, so heavy wool sweaters could be worn comfortably underneath. Jean jackets were the worn for work because they were durable and comfortable. Remember those key points when you put yours on… Are you exuding rugged confidence yet?


Great American men have worn denim jackets as far back as they’ve worn chiseled jaws and broad shoulders. But for the street, you’re aiming for Steve McQueen (see above), not Roy Rogers. Buy your jacket raw, dark and stiff. It should fit trim and smart. Start yourself off with the idiot proof look: Dark denim jacket, white t, Khakis and Jack Purcell’s. It’s no fail, and you can wear it often to get the break in on your jacket started. Once you’ve got a little wear on your jacket, you can brave the waters into hot denim on denim action. Keep you jacket and jeans at least three shades off from one another. A dirtier lighter jacket with darker, newer jeans at first…. Brand new, dark jackets with old faded jeans can be a little awkward sometimes, tread carefully. Perhaps even more importantly is that you wear your jacket like it’s YOURS. Throw it on to add an extra layer to whatever you’d otherwise wear. DON’T fall into the dude ranch trap and add in any more western wear that you’d otherwise put on. Keep it simple, keep it classic.

Remember guys: Your goal is to look like you got dressed purposefully and deliberately that morning, and you haven’t given what you’re wearing a thought since then. Good Luck!

This post was written by Madeline Harmon of Chucks Vintage in Los Angeles and Bill “Broken Twill” Sack


  1. It is about time…The decline of people wearing denim jackets are over. What a great article & love the pictures.

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