Popularized by icons such as James Dean and Elvis Presley, the denim jacket is a timeless piece that belongs in any stylish man’s wardrobe. Beloved by all walks of life — from punk rockers to the biggest names in hip-hop — the transitional staple tends to cash in as relatively affordable outerwear, and while you’ll be familiar with the classics from brands such as Levi’s, iterations abound from workwear and high fashion brands alike.

This season, denim jacket highlights come from iconic ’90s brand Tommy Jeans, Calvin Klein, Helmut Lang, and Raf Simons, among others. Now, we’ve rounded up some of the best denim jackets we’ve come across online in recent times, with styles spanning everything from classic blue truckers that’ll go with every ’fit to bolder graphic-print options.

Scroll on and you’ll see classic designs such as an oversized Carhartt WIP jacket and cowboy-style truckers from Calvin Klein, as well as more head-turning investment pieces from Raf Simons, Y/Project, and Charles Jeffrey.

Michigan Chore Coat

Carhartt WIP


Trucker Jacket M18

Tommy Jeans


Sherpa Trucker Jacket

Calvin Klein


Denim Trucker Jacket

Calvin Klein Jeans Est. 1978


Militia Denim Jacket

Resort Corps


Denim Trucker Jacket

Helmut Lang


Black Denim Pop-Up Jacket



Blue Denim Chalk Madness Jacket

Charles Jeffrey Loverboy


Denim Jacket

Raf Simons


If you want a deeper dive into denim jackets, watch the video below.

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