“As the saying goes, a gentleman should put on his clothes with great care, and then forget about them entirely. Nowhere is this more true than the anxiety-inducing first date: figuring out how to pronounce that intimidatingly priced bottle of Burgundy is hard enough without having to worry about the puff of your pocket square.


First step: skip the tie. It’s a date, not a job interview. Do wear a sportcoat, though. You can’t fail with navy or camel, and both pair perfectly with dark denim (save the distressed look for the third or fourth date). If you go with a navy blazer, try a subtle, blue gingham pocket square; a dark tartan—like black watch—works well with camel. Stick with a flat fold. You don’t want the shrub popping out from under your lapel to distract your date.

You want a point-collar or spread-collar dress shirt. They’re sharper than button-down collars, and sharp is a good thing on a date.

Obviously, you’ve made plans to hit up a casual, insider spot where you’d fit in with a clean pair of versatile, unfussy, suede desert boots. If chukkas are too informal for you, try a sleeker version of the traditional penny loafer.

Either way, a pair of striped socks lets you peacock—but subtly. So does a scarf. And don’t get all matchy-matchy with your belt; the one above works with both pairs of shoes.

Now, just try not to spill anything on yourself.”

(Spotted at Park & Bond)