ask chris black

Ask Chris Black: What’s an Airport Fit That’s Not Too Schleppy?

Photo: Jason Stewart

Chris Black has returned to the Strategist with a monthly column to answer all of your burning questions — from super-specific style predicaments and workout and tennis recs to foolproof host-gift ideas that will get you invited back to the beach house.

Airport fits that aren’t too schleppy? I need a departure from sweats and sneaks.

This is a timely question: I leave for London and Stockholm in 24 hours. As a society, we have settled into slovenly airport dressing, but we must each do our part to course correct. It doesn’t have to cost a fortune to look presentable for a long haul. The frayed SpongeBob pajama pants and Crocs aren’t suitable even for Spirit Airlines.

Everyone gets cold on the plane, so you have to wear something warm on top. A simple cashmere crewneck sweater is the perfect choice that will also most likely come in handy once you reach your destination. I would go with navy or black, but if you have a penchant for color, by all means go crazy. (Full disclosure: J.Crew are a client.)

From $175

If you need something that feels and looks more technical but still provides warmth, go with this zip-up down jacket from Montreal’s Ostrya. It isn’t too puffy to sit in, and it stuffs into its own pocket for storage.

The advent and subsequent popularity of the “jogger” has almost ruined comfortable pants for men. Luckily, Adidas still makes its classic track pants in navy. The style has a seam down the front of the leg that gives them a bit of sophistication. They also have zippered pockets, something that really helps while traveling.

If a track pant is too casual, these twill pants from COS are a nice understated option. The fit is roomier without being sloppy, which will help you stay comfortable on your journey but also let you go straight into any situation when you land.

Shiro is making the best socks in the world. Made in Italy from soft mid-weight merino, these are warm and comfortable but much more affordable than cashmere.

If you’re feeling spendy and want to wrap your dogs in luxurious cashmere, do it in a pair of navy socks from Johnstons of Elgin, which has been doing it since 1797.

I love this style of Adidas — less popular than the Samba or Gazelle but similar enough to get the same effect. This pair in tonal brown synthetic suede is very wearable.

If you must wear slip-ons because you still haven’t set aside time with our friends at the TSA to get your pre-check handled, go with the Birkenstock Boston in black leather. It’s more durable and less cheugy than the popular taupe suede.

What books did you enjoy in 2022?


A well-done satire of the food world, Hollywood, and our general obsession with celebrity culture. “S.E. Boyd” is actually a pen name for a combination of three writers who together nail the over-the-top pretentiousness of high-end restaurants, the morally bankrupt media, and fame. The wild characters are captivating and most likely just exaggerated versions of the celebrities we hear about every day. Can you be authentic and famous at the same time? I still don’t know.

The premise is that Jarvis Cocker, the front man for Britpop legends Pulp, is cleaning out his loft. He explains the significance of a vast array of ephemera, from photos and flyers to chewing gum and childhood toys. It’s a great way of organizing the tale of such a well-lived life. It stops before Pulp even breaks through, so round two is definitely in the cards.

Fitzgerald reminds me of guys I grew up with who, by nature or by choice, choose to live on the fringes for a bit. This memoir is a series of essays that touch on everything from train hopping and family to violence, porn, and body image. It’s funny and heartbreaking but done in a digestible and humorous easy-to-read style. It’s simple, he has seen and done a lot, and it’s fun to read about.

Full disclosure: Ryan is a very old friend whom you probably know from his television show Special or his turn on the Peacock reboot of Queer As Folk. His first novel is essentially about a disabled gay man who blows up his life trying to figure out who he is. It’s hilarious and emotionally complex. It’s perfectly paced, I read it in 48 hours, and you will most likely do the same.

If I’m going to splurge on birthday gifts for myself, what should they be? 

I am not one to splurge on myself; giving gifts is more fun. But if you have your mind made up, we can get into some small luxuries you will enjoy for years to come.

A handmade pair of boots will last a lifetime. This suede pair from Northampton’s John Lobb can be worn anywhere and will age beautifully. The dark-brown suede looks great with jeans, a suit, or any color. You can’t miss.

The passport holder is the ultimate gift for someone who has everything, but it can double as a splurge that, barring a fumble, will stay with you for decades. This black leather version from Tom Ford has room for plenty of foreign currency, important receipts, and other associated travel documents. It’s useful but absolutely unnecessary, a perfect splurge.

If you’re a collector, nothing is a better birthday splurge than a signed first edition. This one from artist Wolfgang Tillmans, his first monograph, expertly showcases his range of work, from casual portraits of friends to abstract images made in a darkroom without a camera. It should bring years of joy and inspiration.

How crazy are you trying to go, chief? I’m not a big watch guy myself, but this Rolex Air King could be the perfect splurge for you. It’s classic and simple and could be passed down for generations.

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’s an Airport Fit That Isn’t Schleppy?