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.

$94 at Entireworld

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.

When it rains in New York City, I see a lot of people wearing Converse Chuck Taylors. A shoe I genuinely love, but makes absolutely no sense for wet conditions. A new method I have noticed is wearing a sandal, and honestly, it makes sense. A pair of streamlined and durable black Chaco Z/1 Classics lets the feet breathe (get a pedicure before wearing), and the lack of socks prevents soggy, wet cotton from ruining your day. At $100, these aren’t cheap for a dedicated rain shoe. But you can wear them on hikes (the straps are secure and provide excellent support) and to the beach. Multi-use sandals are always a solid investment!

If the sandal doesn’t work for you, then you must go with something more HIGH TECH. You need Gore-Tex®, the fabric of the gods, to protect your dogs from those pesky puddles. The La Sportiva Akyra GTX Trail-Running Shoes look incredibly cool and are lined with Gore but engineered to still breathe. Plus, you can comfortably break into a full sprint to make it to Whole Foods before it closes. If you’re not into the black-and-green style, it also comes in a bright blue–and-green version, too.