please advise

Ask Chris Black: What Would You Wear to a Wedding?

Chris Black in Thom Browne. Photo: Daniel Hall

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 turned to resident Cool Guy Chris Black (he’s a partner at brand consultancy Public Announcement) to help us answer both of those questions, and to get 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

Question: What would you wear to a wedding (formal but not black tie)?

Funny you ask. I recently attended a very chic wedding on Harbour Island in the Bahamas. I caught a wild hair and decided to wear a Thom Browne shorts suit. (Full disclosure: I work with them at Thom Browne.) It got some interesting looks and inquiries, but overall it was a hit.

When I’m not going to a Bahamas wedding, I also have a comfortable navy wool Calm Twist suit from Ring Jacket. I would suggest J. Press or Sid Mashburn as well — two strong, timeless options.

The rest of the outfit I keep pretty classic: a fun tie from the masters at Drake’s, a crisp white shirt from Sid Mashburn (or Charvet if you have it like that) and vintage Alden longwings.

As you can tell, I tend to stick to navy suits (black suits can feel a bit waiter-y), but I always add some ~cool~ accessories to make it fun. An indigo dyed pocket square from 45RPM, a colorful lapel pin from RTH (which of course you can’t get online), or maybe just a vintage plain-Jane (plain Jack?) Cartier Tank with a croc strap. If you are feeling wild and flush, make a call and get something custom from Bode.

Question: What are the best black jeans?

Lately, I have been seeing some anti-jean rhetoric online. I, for one, will NOT stand for it. I wear (and will continue to wear) jeans all the time. I like a classic fit — slim but not skinny, button fly, no accoutrements. That’s not necessarily what everyone wants to wear, but it gives you an idea of where my tastes lean. The best advice I can give is to avoid pre-distressing, paint splatters, or a frayed hem. Unless you have a Hot 100 Billboard single featuring Drake, you will look like you are trying too hard.

Levi’s are a time-honored staple, a pillar of any man or woman’s wardrobe. Levi’s basically invented jeans; they make so many versions that everyone can find one that works. The 501 is my choice (mid-rise, button fly, straight leg), but maybe you would prefer the 505 (mid-rise, zipper fly, straight leg), just gotta go try them all on.

I don’t really stray from vintage Levi’s, but A.P.C. makes a really good pair, too, if you prefer something skinnier. RRL (not online!) also.

This version from The Row is really speaking to me right now, but I would have to get special permission from my financial institution to spend $650 on jeans. Oh well.

The Strategist is designed to surface the most useful, expert recommendations for things to buy across the vast e-commerce landscape. Some of our latest conquests include the best acne treatments, rolling luggage, pillows for side sleepers, natural anxiety remedies, and bath towels. We update links when possible, but note that deals can expire and all prices are subject to change.

Ask Chris Black: What Would You Wear to a Wedding?