The best denim shirts for men have reached heights far beyond their humble beginnings. Popularized in the early 20th century by the ranch hands and roughnecks of the American frontier, the rugged button-up has long since earned its place in the canon of hard-wearing, easy-going menswear classics. Unlike the plaid flannel, white tee, or chore coat, the denim shirt has managed to work its way into the snooty, sartorial upper echelons of tailoring, too.
These days, some boast spread collars for tucking under a lapel or shell buttons to balance a lustrous wool gabardine blazer, but all are ready to add a hit of workwear-inspired swagger to your everyday lineup. Just look at fellas like Steve McQueen, Tupac Shakur, and Pedro Pascal, who’ve made the denim shirt an essential part of their wardrobes. (And that’s to say nothing of Ralph Lauren, who’s been schooling the world on how to wear a denim shirt with panache for over 50 years.) These days, there’s a wider array of denim shirts than ever before, from authentic sawtooth western joints crafted from Japanese selvedge to cozy flannel-lined jacket hybrids to elevated riffs done up in crisp white Italian cotton. Try one with a blazer and weathered khakis or as one-half of a Canadian tuxedo, and don’t be surprised—or remotely disappointed—if you find yourself reaching for it day after day.
Rest assured, you’re in good company. If it’s authenticity you’re after, you’d best go straight to the source. Levi's has been outfitting folks in sturdy cotton workwear since 1853, and no other brand has a better claim to establishing blue denim as a mainstay of Americana style.
Unlike their iconic dungarees, which became popular with miners and railway workers in the late 1800s, denim shirts didn’t become part of the Levi’s catalog until the 1930s, when they were adopted by ranch hands, cowboys, and city slickers looking to ape their rugged frontier style. True to those origins, this version features authentic vintage details like western pockets, pointed front yokes, pearl snap placket with faux mother-of-pearl buttons, and a just-right mid-blue rinse. As in the 1930s, there’s no better way to add a dash of western swagger to your look without going full Midnight Cowboy.
Fabric 100% Cotton denim Fit Slightly slim Washes 7 available Sizing XS-XXL Real ones know that sometimes the best shirt isn’t just a shirt. It’s one that can play different roles at the drop of the hat, from everyday button-up to light jacket to rough-and-tumble work shirt. J.Crew’s classic denim shirt has been in its catalog for as long as this writer can remember and it’s obvious why.
It’s sturdy and densely woven, but softened into a vintage feel with a few different washes. The double flap chest pockets, pencil slot, cateye buttons, and contrast double-needle stitching come together to tie in the workwear inspiration, and the relaxed-but-not-sloppy silhouette make it perfect for wearing as a light layer or on its own. It feels like the kind of shirt you’d be happy to acquire from your grand pappy, or find hidden deep within your favorite vintage store, ready to synchronize with every pair of pants you throw at it.
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