Say dress shirts, and "The Son of Man" instantly comes to mind—at least for me. 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 I 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-up, 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 buttoning down their button-ups. Temptations abound.
Now, there are 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 15 of the best for work, for dining, or, if you're so inclined, stealing eight-figure paintings from The Met.
Lavender Twill Dress Shirt
You're going to love the way you look in this Joseph Abboud dress shirt.
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.
Easy Care Checked Stretch Slim-Fit Long-Sleeve Dress Shirt
Uniqlo, per usual, offers a quality style at a price point that's almost too good to believe.
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.
The Standard Fit Performance Dress Shirt
Everlane offers timeless pieces—including this dress shirt—that won't fail you. I've said it many times before, but when something is this good, it bears repeating.
Slim-Fit Ludlow Dress Shirt
At this point, J.Crew's Ludlow needs no introduction. But if you need a refresher, it is the name of classic suits and shirts that will work for business meetings, barbecues, weddings, dates, what have you.
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 Commuter Dress Shirt
Like Lululemon, 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.)
Stretch Milano Slim-Fit Dress Shirt
A.P.C.—the master of easy, elevated dressing with a French bent—has a linen shirt that'll truly make life a breeze.
Modern-Fit Solid Dress Shirt
Takes some style cues from George Clooney, a man who consistently shows how a boss wears a black shirt, preferably from Armani.
'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.
Aston Striped Tailored Long-Sleeve Dress Shirt
Ralph Lauren Purple Label
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.
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 I say more?
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 imbue quiet luxury.
Barry SamahaBarry Samaha is the style commerce editor at Esquire, where he covers all things fashion and grooming.
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