Welcome to the Investment. These are the pieces—a little pricier, a lot nicer, and entirely worth the money—that our editors love and respect. The picks with a story to tell and a real reason to exist ...

The Gucci horsebit loafer is an icon. Not just because Esquire said so—though we did, and we even made a whole video about it—but because the design has proven itself again and again over the ...