If we’re living in an age of hats—and a glance around New York’s bars and clubs suggests that, yeah, we are—seems now’s a pretty good time to get one that actually fits. To the rescue comes Optimo Hats, one of Chicago’s premier haberdashers, who custom-makes its fedoras, trilbies, porkpies, and homburgs. (It’s all possible thanks to a 100-year-old head-measuring machine called a conformer, which, Optimo’s Graham Thompson insists, only looks like a torture device.) Until now, getting f itted by the guy required a trip to the Windy City, but Thompson is now in NYC for the company’s first (hopefully annual) trunk show. His hats aren’t cheap—felt models begin at $600, and panama hats can rise above $1,000—but the high quality makes for versatility: Since they aren’t pressed into one shape, you can tweak the brim and shape and style them differently depending on the day. Which is exactly what you’ll want to do when you’re dropping up to four figures. Optimo fan Johnny Depp (who wore a few in Public Enemies) can probably afford a hat for every mood, but you’ll want to stick with one (to start, at least). Good news is, that one will look good—both in style and in shape—for a long time to come. It’s a hat to grow into, not out of. Your fitted ball cap? Not so much.
