How to Style a Jean Jacket

My first jean jacket came from a garage sale in the suburbs of Iowa. Out on a scooter excursion with the child I was nannying that summer, I placed a kid’s toy and the Levi’s classic on a card table. Five dollars felt expensive, when that was about my hourly rate. “You’ll have this forever,” the woman said, folding the jacket into a plastic bag that bounced as it hung from my scooter’s handlebars as we rode home for naptime.

That woman at the garage was correct. Denim jackets are about as close to timeless as any one article of clothing can be. Variations arise with the ebb and flow of trends, but a simple, heavy version in a mid-wash looks as natural on James Dean as it does on Michelle Obama.

Of course, the Americana-inspired jean jacket is always going to be one of those classic staples that will hold timeless appeal. Just like a khaki trench, it’s an essential style item that seems to find a secure spot in our wardrobes year after year—even if it spends a little time in-between hanging in the back of your closet.

For those who may have been keeping their blue jean babies tucked away, here are a handful of no-fail tips from denim experts that are sure to help inspire a whole new era of denim jacket-wearing for you. Read on for their advice on how to style a jean jacket now.

The lived-in look

Despite the many tempting versions and inventive iterations of reworked denim pieces—like cropped jackets, full skirts, and even shoes—we can’t underestimate the power of a jean jacket in its most original form. There’s something to be said for the iconic button front with two front chest pockets and cuffs, and its wonderfully worn-in feel.

Tess Sullivan, head of design and creative at Buck Mason, agrees that a great denim jacket depends on the details, specifically, “rigid 12-13 oz cotton twill, built with authentic details, and a great lived-in wash: The more life it looks like the jacket has seen the better.” Sullivan has built the sartorial world of Buck Mason’s womenswear to feel like the kind of store frequented by your friend who’s always “stumbling” upon vintage lamps at the Rose Bowl or road tripping through Wyoming; it’s cool, but not aloof. A great jean jacket feels the same.