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Ask Chris Black: Can You Recommend a Few Good (and Good-looking) Duffel Bags?

Photo: Eric Chakeen

If you’re looking for the most powerful hair dryer or the 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? Chris Black (he’s a partner at brand consultancy Public Announcement) is here to help, in the form of 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

Curious about your thoughts on good duffel or weekender bags. I liked the North Face duffel you included with your recent luggage recommendations, but I am wondering if you have more options, including some less sporty styles?

Taking bae upstate to see the leaves change? I love it. Yes, a Rimowa would be overkill; you need something you can toss in the trunk with ease. If you aren’t ready to pony up for the Louis Vuitton Keepall, I can recommend some affordable (and durable) options that will do the job.

The Filson Medium Rugged Twill duffel bag will easily fit everything you need for a weekend of apple-picking or skipping rocks on Long Island, without taking up too much space in a car or on a train. If your weekend plans require plane travel, that’s also just as easy since the duffel is designed to fit in carry-on compartments, according to Filson. It comes in a handful of colors beyond the classic tan, including olive green, navy, and a gray called cinder. Plus, it’s water-resistant, has solid leather handles, and Filson will even monogram the leather if you buy it from the brand! We love a monogram.

If your weekend away includes grass tennis courts, gin martinis, and skeet shooting, the new Classic Duffel from J.W. Hulme will do the trick. The bag is beautiful, functional (it’s carry-on appropriate and comes with a shoulder strap), lined with micro-suede, and has a U-shaped zippered entry to the main compartment for easy access. You can also get it monogrammed for an extra $10. Throw it in the back of your old Land Rover and hit the road. (If you like the look but want to spend $100 less, J.W. Hulme makes a slightly smaller Continental Duffel that has a similar design.)

Maybe your weekend away involves (gulp) tailgating. Lucky for you, the cooler gods at Yeti also make a fully waterproof duffel bag constructed of what they call high-density nylon. If your date spills her White Claw while celebrating an impressive kickoff return, you won’t have to worry about your gear getting wet.

I wouldn’t be doing my job if I didn’t offer at least one extravagantly priced, excellent option. Another nylon duffel, Prada’s black Holdall is an investment worth making. It is something you can pass on to the kids; until then, it will fit perfectly on the PJ from Teterboro to Miami.

What are good black shoes for a not-cool person who doesn’t like the look of black sneakers? I tried the Dr. Martens shoes you wrote about, but I can’t pull off the bulky shoe look.

Hey! I am sure you are cool in your own way :). TBH, I never thought of Dr. Martens as bulky, but I am happy to provide some different options. It is literally my job.

I think you should dip into the Clarks pool. The low-top Wallabee in black beeswax leather is a classic worn by all my guitar-playing British heroes, but also by, like, my Dad. If the shape throws you off, get a pair of Desert Boots in black suede. They are super-wearable and eternally cool.

Some Tricker’s brogues are perfect for every occasion and will last forever. I like the slightly chunkier sole, which makes them feel more substantial. They might seem too bulky for you, but I say try them on before ruling them out.

These zip-up Our Legacy boots also really speak to me. Black leather, Vibram sole, minimalist … seems like they could work for you? Just don’t try to wear them with khakis or something.

While we’re talking shoes: What kind should I wear with a slim pair of black jeans? I’ve worn Dickies exclusively for the last year, and I’m feeling lost with fabric in the vicinity of my ankle.

I mean, almost anything? You can never go wrong with a pair of Converse Chuck Taylor ’70 high-tops. Coke white, of course — or sunflower if you need a little color.

As you know, my household is checks over stripes forever. But, I don’t expect everyone to be as brand loyal as myself, and to those who are not, I say: Get a pair of suede Adidas Gazelles in collegiate navy to wear with your skinny black jeans.

Maybe you are trying to swag out a bit. I love these navy suede Playboy Chukka boots from Sid Mashburn. Your classic British-army shape with a crepe sole. Go off. Not ready to go full-on blue suede boots? The black pair of Desert Boots above offer a more neutral take on the look (and come at a lower price).

If you have had your biweekly pedicure (or are confident enough to do the socks and sandals thing), stunt on ’em with a black-and-navy pair of two-tone Visim Christo slides. A sandal with a Vibram sole, you love to see it! These are OG, accept no imitations.

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Ask Chris Black: Can You Recommend a Few Good Duffel Bags?