The Best Button Down Denim Shirts for Men

You could very well call the Levi’s Barstown Denim Shirt “the original and best” as far as denim shirts are concerned – the company helped pioneer denim in the United States, after all – and you’d be right on the money.

It’s a certified classic for a reason, hitting on all the right notes, from the pointed shoulder yoke detailing to the V-shaped front chest pockets. The Light Wash color is classic and makes for a solid style purchase when paired up with dark blue, black or grey denim, and it helpfully retails for well under $100.

Some of the best denim shirts are so cool and utterly rugged, they look like Clint Eastwood or Steve McQueen wore them right off screen and into the real world.

The RRL Type 2 Denim Jacket leans into Ralph Lauren’s classic Americana designs in a major way, reinventing the famed Type 2 Trucker Jacket style for the modern man.

It’s made from tough selvedge denim that will wear in handsomely over time, and the use of Japanese cotton fabric puts it a cut above other denim shirts on the market. In short: It’s worth the higher price tag.

The best denim shirts call to mind another time and place, like the vintage appeal of Taylor Stitch and its distinctive take on the Western shirt.

Organic cotton selvage denim delivers both softness and standout durability (the shirt is washed for a lived-in feel), while the faded color itself looks like you’ve had it for years.

When paired up with contrast stitching, slanted Western-style chest pockets and YKK Western snap buttons, it’s a perfectly executed take on the denim shirt. Bonus points for the fact that you can wear it open over a Taylor Stitch tee, or buttoned up beneath a shawl cardigan.

For a brand that was originally inspired by the rough-and-tumble, hard-working factories of Rust Belt cities, it makes perfect sense to carefully craft one of the best denim shirts on the market.

All the bells and whistles you could ask for in a denim workshirt are front and center, be it the indigo yarn-dyed denim (in a layering-friendly 7oz. weight) or the double-needle felled seams for long-lasting durability. Side seam gussets (a fabric patch designed to improve mobility) make this a proper workshirt pick for the garage or the shop, but the rich denim color is stylish enough to serve as an off-duty shirt jacket, too.

The denim shirt is such an all-American staple (thanks to brands like Levi’s – keep scrolling for more) that it only makes sense that one of the country’s current top designers would offer up his own remarkable take on the style.

100 percent Japanese cotton denim – some of the best fabric on the market – elevates this denim overshirt in a major way, while oversized melamine buttons and two chest pockets give it a tried-and-true shirt jacket feel. It also comes in a raw Japanese selvedge, but the Stone Wash iteration is casually cool and pairs nicely with dark blue jeans.

“If it ain’t broke, don’t fix it” is an adage that could very well apply to this iconic denim shirt from another lauded all-American menswear brand.

The Shoals Denim Shirt is a longtime favorite of the Alabama-based designer, who’s carried it in his namesake line for nearly two decades. The details have remained largely the same, from the eye-catching angled front snap pockets to the antique brass snap buttons.

Reid himself loves the shirt, and it’s not hard to see why: The soft denim fabric is comfortable as a shirt on its own, yet easy enough to layer over a henley shirt in cooler weather.

Channel the OG workwear roots of the denim shirt with this trusty, reliable number from Flint and Tinder. The look and feel of the shirt falls right in line with other rugged style moves from Huckberry’s in-house brand, like its Waxed Trucker Jacket, but it’s a better move if you want a lightweight workshirt to throw on at a moment’s notice.

The mid-weight cotton denim should prove especially easy to layer over T-shirts and henleys in at least three seasons, while the pleasantly faded real indigo dye is only going to show off more distinct character over time. Front flap chest pockets deliver crucial workshirt EDC storage, and cool contrast stitching delivers a nice stylistic touch.

Want a classic denim shirt that more closely rivals the casual, cool flair of your favorite Oxford shirt than a Western shirt? Orvis is right on the money with its Wrinkle-Free Denim Shirt, a lightweight 4.5oz. cotton denim shirt in a deep indigo blue color.

That color gives it a dressy look and feel that could even work well with tan stretch chinos and brown leather chukka boots in a business casual office setting. Plus, this shirt’s details are subtle and timeless, like the buttondown collar and a single button chest pocket.