We’re all about investing in the best menswear for multiple seasons, and in this case, the kind of workhorse pieces that can carry you through the dog days of summer and on into fall.
While every rotation of the best men’s shirts should have multiple options at the ready (think a classic Oxford shirt for Zoom calls or the office, a lightweight linen shirt for summer, a durable flannel shirt for fall), what if you really want a shirt you can wear as the seasons change—without missing a beat? Let’s be more specific: Right now, you need a rugged denim shirt to close out summer and cross the finish line at Labor Day, then keep on going right through the weeks ahead.
The best men’s denim shirts offer wearability with lightweight chino shorts and canvas sneakers just as readily as they can team with your favorite henley and black denim as the leaves start to change. Designer and luxury-minded options abound, as do more affordable denim shirts you can add to your wardrobe this instant. When you want a cool-as-hell shirt you can throw on and look great wearing, you want one of these denim shirts.
Billy Reid Bleach Wash Denim Shirt
One of America’s foremost menswear designers offers a laidback, rugged-yet-cool-as-all-get-out take on the denim shirt, featuring a pleasingly summer-friendly bleach wash, antique brass snaps, contrast stitching and the ability to pair up with chino shorts (for summer) or black denim (for fall). Crack a Miller High Life for happy and call it a day. $195
GAP Slim-Fit Denim Shirt
Consider an affordable denim shirt that toes the line between summer and fall the kind of workhorse shirt you can wear darn near all the time through August into one of the best seasons of the year (in our humble opinion). GAP delivers a lightweight, bleach wash chambray for expert pairing with dark denim and brown leather chukka boots. $38
Todd Snyder Indigo Denim Buttondown Shirt
This Portuguese-made Italian top is one of the more premium takes on a denim shirt we’ve seen, complete with a front-button chest pocket for more visual interest. You can wear it with darn near anything from summer into fall, including olive chinos and classic beeswax leather chukka boots. $148
Wrangler Icons Denim Shirt
Style and sustainability is the name of the game when it comes to this classic Wrangler denim shirt. It’s made with the brand’s Indigood sustainable dyeing process, featuring 100 percent less water usage, to go along with 60 percent less water and 60 percent less energy than the conventional process. $89
Levi's Barstow Western Shirt
It only makes sense that Levi’s makes a rugged denim shirt in a classic Western-style cut. It’s the ideal pairing with—yes, you guessed it—slim Levi’s jeans in an inky dark blue. For August, you should also feel free to wear it with tan chino shorts and that pair of canvas sneakers you’ve rocked (stylishly) all summer. $70
Brunello Cucinelli Washed Denim Shirt
This slim-fit washed denim shirt is as premium as it gets, made to exacting standards and featuring a dressy cutaway collar, the sort you can pair with a tweed jacket this fall. And in the interim, wear this handsome denim dress shirt up until Labor Day with white denim and brown suede loafers. $495