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Ask Chris Black: ‘I Want to Get Into Blazers. How Do I Keep It Casual?’

Photo: Tim Coleman

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.

I want to start wearing blazers without feeling too formal. Where do I begin?

It’s all in the styling, my friend. If you wear it casually, it won’t feel formal. Think ’90s movie stars in the airport: Bruce Willis, Kyle MacLachlan, Denzel Washington. No one did it better. You cannot let the blazer wear you!

This unlined mohair double-breasted blazer from Our Legacy Workshop is inherently casual and pairs well with jeans. The navy feels a little less formal than black.

Wearing a blazer with jeans seems easy, but it has to be the right jeans. If they are new, the wash has to be perfect. This pair from orSlow is based on a vintage cut and color and are made from Japanese 13.5-ounce denim.

A simple white button-down always pairs well with jeans and a blazer. This one from Stockholm’s tailoring wizards, Saman Amel, is a little looser and has a cool one-piece collar.

If a button-down feels too formal, go tonal with a T-shirt. This navy broken-in version from J.Crew (one of my employers) is the next best thing to vintage. It’s not too fitted but long enough to tuck in.

You gotta tuck in your shirt. It’s just how it is. That being said, a cool belt is important. I just got this one from Noah, and I love it. Real croc can be costly, but stamped leather works just fine. The metal tip gives it just a bit of western flair.

To be very clear, sneakers aren’t an option. You don’t want to look like a former crypto millionaire. A nice pair of sturdy boots feels very cool and less formal than loafers. This pair from Lemaire has a little western flair (like the belt) and will age beautifully.

Do I want to get into speakers? How are you listening to music?

This is a fun question because many of you have gone full audiophile nerd and need to be brought back to earth. Unless you make music professionally, you can live without the perfect Ojas system in the apartment you share with three friends. Mostly, we all listen to compressed mp3s from a streaming service. You just don’t need studio monitors to listen to NBA YoungBoy at the pregame before you hit the club with your crew. With that in mind, here are some simple and affordable suggestions.


This is what I use, and I love it. It is small enough to move from room to room, the charge lasts for a long time, and its understated design works in any environment. It also gets loud if you are into that sort of thing. You can use Airplay from your phone or computer to bypass the clunky Sonos app.

I love how this thing looks. Classic enough, but the matte-black finish gives it a more modern feel. It has some bells and whistles: You can rewind or slow down playback and choose from 35 recorded tracks designed to help you relax. It has four front speakers and bass on the sides — the aesthetic winner of the lot.

This is the smallest and most portable of my picks. You can easily throw it in a suitcase for a weekend away or just keep it at your desk. It sounds crisp, and the bass comes from the back of the speaker, which works.

How can I carry my phone — in a practical and cool way — while running?

This is a tough question. You still see people clocking miles with the see-through pouch wrapped around their bicep like a blood-pressure testing machine. We can do better.

You have to shimmy this on like a pair of underwear, which isn’t great, but its seamless design makes it more comfortable. It has multiple spaces for your phone, keys, trekking poles, etc.

This thing punches above its weight. It’s deceptively small, it stretches, and it can easily fit a phone. It’s only one zipper pocket, so adding keys, cards, etc., doesn’t work that well.

If you are doing big-boy weekend runs and need more storage for gels, water, or a banana, this heftier version from Patagonia will sort you out. The three-pocket design distributes weight evenly so you aren’t jogging lopsided.

Any styling tips for tall men? I’m six-foot-eight and struggle to find clothes that fit and look cool.

For this question, I had to tap in with my How Long Gone co-host, recovering DJ, home cook, and known tall person (he is six-foot-nine) Jason Stewart.

“I won’t give you any secret tips because you’re right. It is hard to find clothes that fit and look cool, but I’ll point you in the right direction. Look for brands that even carry tall sizes, and start there. Luckily, Brooks Brothers, J.Crew, and Ralph run tall shops, and everyone can find something from that collection for basics. Brooks Brothers are great for formal stuff, and you can search shirts by sleeve length, which is unheard of anywhere else I’ve looked. Otherwise, it’s a needle-in-a-haystack online quest for shirts with long enough sleeves and unhemmed pants where you can take them to your tailor for a false hem. Typically, any pair of trousers listed with an inseam of 39 inches or higher will be unhemmed. J.Crew is great for more casual dress shirts and plain crewneck sweatshirts, and who doesn’t love a classic polo color?”

Measure your neck and arm length and load up Brooks Brothers to find your exact size; it fits every time. There are dozens of styles, but I chose the Japanese Knit because it’s the most expensive and looks nice.

I’m wearing this crewneck right now, size large tall. My Instagram to see. I have this in black and navy, but regal blue is a nice pop sometimes.

A long-sleeve polo can help dress up a pair of shorts when you need to look more presentable at the BBQ. They come in a wide range of sizes, but the one you want is usually sold out.

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Ask Chris Black: ‘How Do I Make a Blazer Look Casual?’