20 Dress Shirts to Make You Feel Like the Gentleman You Are

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Say dress shirts, and “The Son of Man” instantly comes to mind—at least for some. It's a painting by René Magritte, reputedly a self-portrait by the famed Surrealist, that depicts a gentleman standing erect in front of a wall, looking forward, his face covered by an oversized green leafed apple. He wears an unmissable bowler cap, gray overcoat, red tie, and a dress shirt, this one with a point collar. It is a representation of civility meeting temptation, a work that reflects one man and every man. Fans of The Thomas Crown Affair remake will understand what we mean.

The character doesn’t waver, covered in a crisp white top that comes near his jaw line. This is the prototypical dress shirt: a button-upw, a symbol of propriety and decorum. But by the mid-'60s, when the painting debuted, changes in manners and fashion arose. Collars and silhouettes became oversized or shortened, and bright colors and patterns became prominent. Also, men started dressing down their button-ups. Temptations abound.

Now, there's a variety of dress shirts: some rakish, some louche, and others completely laid back (Benjamin Bratt displays all these vibes in this Esquire spread). But even with these mutations, the style overall is still a class apart. Over the tee, tank, polo, turtleneck, and every other top except the tuxedo shirt, it is the dress shirt, even if cast in pink and unbuttoned to the navel, that remains the most gentlemanly of the bunch. And we have 20 of the best for work, for dining, or, if you’re so inclined, stealing eight-figure paintings from The Met.

Slim-Fit Herringbone Non-Iron Dress Shirt

Calvin Klein, the brand that ushered in minimalism in the '90s, continues to offer unfussy styles that'll work for one and all.

Venture Long Sleeve Dress Shirt

Few—and we mean very few—can surpass Lululemon's ability to offer sleek, uber comfortable styles meant to move with you. This, of course, includes its stellar collection of tailored pieces.

Slim-Fit Traveler Stretch Dress Shirt

Levi's is to jeans as Van Heusen is to affordable dress shirts. That pretty much sums it up.

'Dr. No' Blue Cotton Dress Shirt

From Sean Connery to Pierce Pierce Brosnan to Daniel Craig, Turnball and Asser, England's premiere shirtmaker, has outfitted the top three actors to play James Bond (sorry not sorry, Roger Moore fans) in its dress shirts. And here is the same style that 007 wore in Dr. No, which makes it a definite yes.

White Double-Cuff Cotton Dress Shirt

The center of the shirting world is located in a six-story townhouse on the Place Vendôme in Paris, the HQ of Charvet, the oldest and the best shirtmaker in history. Need we say more?

Super Non-Iron Slim-Fit Long-Sleeve Shirt

You don't have to break the bank to look expensive and sleek, as Uniqlo proves. This dress shirt is simple, classic, and just under 40 bucks—the ultimate trio, if you ask me.

Wrinkle-Resistant Grid Check Shirt

Gone are the days of your dress shirt being ill-fitting, wrinkly, and just all-around uncomfortable. Stantt is changing the game with its completely customizable, wrinkle-free shirts. Plug in your collar and sleeve size, preferred fit, and preferences for a collar, cuff, buttons, front, and pocket, and voilà: a completely custom, personalized dress shirt is yours.

Tailored Slim Premium Poplin Dress Shirt

When it comes to dressing up, a quintessential fabric to keep in your rotation is poplin. This slim-fit option from Banana Republic has a tailored look, so you'll always feel your best in it.

Solid Navy Stretch Dress Shirt

Dressing up doesn't have to mean you feel stiff and formal. Thanks to a stretchy fabric that allows for all-day movement and comfort, this elevated option from Canali is one of our favorites.

Oxford Shirt in Standard Fit

No frills, no fuss—Gap has a simple, timeless white dress shirt that you can style under a blazer or a sweater, or even over a tee, if that's your vibe.

Jetsetter Stretch Dress Shirt

Bonobos is a household name in the world of dress shirts, and for good reason. The brand's iconic Jetsetter shirt is comfortable, stretchy, and infallibly chic.

Dress Shirt

We live in a day and age where you can get a Tommy Hilfiger dress shirt for around 30 bucks on Amazon, and boy am I glad for it. Tried and true, this gingham option is a reliable choice that effortlessly pairs with chinos, khakis, jeans, or dress pants.

Roan Kent Slim Fit Foulard Print Cotton Button-Up Shirt

From BOSS comes a tailored-look that keeps things a little bit playful, too. Don't be afraid of a little print or pattern!

Aston Striped Tailored Long-Sleeve Dress Shirt

If England has Turnball and Asser, the U.S. has Ralph Lauren Purple Label, a collection of pieces that are made of the finest materials and tailored to the nines.

Striped Cotton Shirt with Pocket

Gucci is celebrated for its ornate collections, filled with looks that crank up the volume. But break them apart, and you have some incredibly tailored, incredibly well-made styles that impart quiet luxury.

Ludlow Premium Fine Cotton Dress Shirt

At this point, J.Crew's Ludlow needs no introduction. But if you need a refresher, it is the umbrella name for the classic suits and shirts that will work for business meetings, barbecues, weddings, dates, what have you.

The Organic Oxford Shirt

Everlane offers timeless pieces—including this not-too-dressy dress shirt—that won't fail you. Plus, it's made from organic cotton.

Commuter Shirt

Rhone is an activewear brand that offers dressier styles with such ample stretch and comfort that you might want to work out them. (Probably don't, though.)

Classic-Fit Twill Dress Shirt

This one is infallible. Clean, dressy, and sleek, it makes for the perfect companion to just about any jacket or suit.

Trofeo Checked Cotton-Poplin Shirt

In a chic pale pink, Zegna's spread-collar, poplin shirt looks as good as it feels.

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