The 15 Best Dress Shirts to Make You Feel Like the Gentleman You Are

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 proprietary 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.