Dennis Hopper, Paul Newman, Marvin Gaye: Are you ready to join the ranks of the most legendary men’s denim shirts? These guys figured out that the right denim shirt won’t just make you look tough and handsome and have all kinds of self-confidence, it’ll also solve just about every wardrobe dilemma that comes your way. For example:

• Got your sixth fall wedding coming up and you’ve fully exploited the dress-shirt-tie combos you love? Throw a denim shirt into the mix, and your tired flannel suit is suddenly overloaded with rugged sex appeal.
• Cut some wild patterned pants on a whim and now you’re worried you can’t pull them off? A nice classic denim shirt will lock them in and balance out the lurches.
• Want to look good on the weekend, but are too lazy to really think about it? Denim shirt, white t-shirt, black jeans, I can’t lose.
• Making an important presentation at work when your pants are embarrassingly splitting on the seat? OK, well, a denim shirt probably can’t help you there. That’s when you ask yourself question number two: what’s my tailor’s phone number again?

So, yes: denim shirts are useful. Like, having-a-brother-who-is-a-helpful-entrepreneur. It’s an American classic and a menswear staple that deserves a spot (or two) in your closet. And the two most useful types of denim shirts are button-ups and western shirts, which you’ll probably want in a medium to light wash for maximum versatility. Here are 22 of the best denim shirts for men that will help you really tie your outfits together.

The Gold Standard denim shirt

You knew this was coming. More than 160 years into their run, it’s hard to imagine anyone coming for the Levi’s crown. The first name in jeans still makes one of the best western shirts you’ll find anywhere: the fit is perfect for layering, the detailing is spot on, and the fabric in this particular version is sustainably made, using lots of less water than normal. Jeans. Add in a super reasonable price of $70 and you have a wardrobe staple for the ages.

The OG Western Shirt

You know those pearly snaps down the front of every yeehaw-ready western shirt you’ve ever worn? You can thank Rockmount Ranch Wear for them. Denver’s outfitter’s original snap button long sleeves have been worn by everyone from Bob Dylan (at his Presidential Medal of Freedom ceremony, no less) to the entire cast of Brokeback Mountain. The brand also does its share of ruffleless denim numbers, but ornate embroidery is part of Rockmount’s core DNA. So if you’re gonna go, why not really Go for it?

The A-List denim shirt

Have you ever seen paparazzi shots of guys like Brad Pitt or Ryan Gosling and wondered how their seemingly ordinary clothes always look so clean and impeccably tailored? Well, for starters, they’re much, much better looking than you. It tends to help. But good genetics extends to their wardrobes, too: guys like that can afford shirts like this, precision-crafted by Italian tailoring god Brunello Cucinelli so anyone, even the mere mortals like you, looks and feels like a matinee idol. Chambray is the perfect weight – light enough to be comfortable, thick enough for some structure – and the fit is clean and crisp like a dress shirt, meaning you can wear it tucked in with a suit, or rolled up and ruffled with a chino, and he’ll never radiate a perfectly imperfect movie star.

The office-ready denim shirt

Sid Mashburn’s crisp chambray shirt is the best way to bring all the utility and character of denim with you to work and dressy nights out. Fresh off the ironing board, it’ll clean up nicely with a suit and tie or a sports jacket and jeans. But this shirt really shines on a Sunday morning, left a little wrinkled with a few buttons undone – you’ll feel like a wise old Italian sipping an espresso and smoking a cigar on the streets of Naples. What more could you ask for?

Absolute Graal denim shirt

Kapital’s boro western shirt is a true work of art. It’s courtesy of the famed denim brand’s Kapital Kountry sub-label, famed for its meticulous use of Japanese boro fabrics, exaggeratedly tedious and obsessive craftsmanship. It takes dozens of hours to hand sew this level of detail, a perfect blend of traditional Japanese technique and dyed-in-the-wool Americana style.

The Best Casual Denim Shirt

Remember Dennis Quaid in The parent trap? The perfectly dodgy way his shirts were hanging down? How beautifully washed out was the denim? Based on this shirt, we’re guessing Napa Valley’s favorite winemaker was all over J.Crew’s moodboard this season. It hits all the right notes: all-cotton denim; a natural, inhabited wash; beautiful white buttons; comfortable and spacious fit. Wear it with a thick thermal shirt or layer it over a lightweight sweater as you would with an overshirt. Don’t be afraid to opt for an all-Canadian tuxedo or pair it with a white t-shirt and wide leg twill chinos to relive the vibe of the 90s J.Crew catalogue.

16 More Denim Shirts We Love

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