please advise

Ask Chris Black: What Should I Wear on a First Date?

Photo: Cobey Arner

If you’re looking for the most powerful hair dryer or handiest chef’s knife, those things can be easy enough to find. Other objects of desire are a little more taste-based. What’s the next status water bottle or hand wash, for instance? Regular readers of the Strategist will know that we’ve previously turned to resident Cool Guy Chris Black (he’s a partner at brand consultancy Public Announcement) to help us answer both of those questions. For more of Chris’s advice, he’s now answering reader questions for us in a regular column. If you have a burning question about the next fanny pack or Noah rugby shirt, drop us an email with the subject line “Ask Chris” at

I’m getting back into dating. What types of clothes would you recommend to make a stylish (but subtle) first impression?

Leave the Balenciaga and Fear of God in the closet. You’ve got to avoid logos or anything that even looks like an attempt to scream, “I’m rich!” I’d recommend a simple, understated outfit that lets your good looks and captivating personality do all the talking.

A cotton single-pleat chino in navy from Entireworld would work well. It’s a classic look, but the single pleat lets your date know you care more about style more than the bankers in Bonobos and Hugo Boss that she usually goes out with.

If that’s too fussy, reach for you trusty Levis 501s. A home-run pair of pants for any occasion.

Photo: Arian Camilleri/Arian Camilleri

Since it’s the dead of summer, pair it with an Alex Mill slub cotton T-shirt in white. Not too thin, not too thick, and of course, fits well.

If you need something a little more formal, go for a Sunspel cotton-piqué polo shirt in navy or white. Sunspel’s polos are logo-free, and made of super-soft Pima cotton.

For your feet, I suggest a pair of classic grey New Balance 990v4s. They are comfortable, and she will like them because the sneakers remind her of her dad.

If New Balances seem too casual for a Friday night at Flora (get the purple endive salad), then pull out the Bass Weejuns (make sure they are polished). But the real key to looking good? Pick up the tab. Nothing looks worse than being cheap.

Any recommendations for a go-to (unisex) summer rain shoe? Ideally something less suffocating than a full rubber boot, and less precious than any of the sneakers or sandals in my daily rotation. But, of course, still looks nice.