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Ask Chris Black: If You Had to Dress Business-Casual, What Would You Wear?

The author, who is currently in Istanbul, keeps it fresh with a “traditional Turkish shave.” Photo: Alix Rutsey

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

If you were forced to wear business-casual attire to the office, what would your work wardrobe look like? 
Absolutely, positively, could not be me, TBH. But for the sake of this column, we can pretend. This is an excellent opportunity to flirt with uniform dressing. Keep the palette simple and the cuts flattering, baby!

Photo: Courtesy of the vendor

Start with some navy pants from Acne. They’re easy to wear with a button-down — straight-leg cotton twill is not hard to pull off — and surprisingly well-priced, considering that Acne stuff typically holds up for several years. On days that are more business than casual, these will also pair well with a blazer worn over your shirt.

Often overlooked, a traditional roll-neck would work great is most offices (sorry finance bros). This cashmere one from Uniqlo is useful in almost every color, but I would go with navy or black. If the roll-neck seems too much, I say live a little. If living a little seems too much, you can always go with one of Uniqlo’s more traditional cashmere crew necks (I am a big fan of the brand when it comes to affordable, presentable basics).

Of course, you’ll probably want — no need — a good button-down or two. I’ve already gone in on my favorites, but for your purposes, I will reiterate my praise for Brooks Brothers’ Regent Fit Oxford Sport Shirt, which comes in light blue in addition to white. It is heavy-duty (meaning it will last) and cut slimmer, which is always a good look for a button-down.

If you need an extra layer, Uniqlo’s fluffy cardigan made of so-called Sherpa fleece is perfect for staying warm when your boss refuses to turn down the air-conditioning. Keep it tonal.

The Dr. Martens Adrian tassel loafer in smooth black leather has a nice chunky sole, but can still pass for business casual. I think? The shoes are cool, regardless! Now go hang out by the water cooler in style.

What are your thoughts on leather jackets?
They seem to work well for basic girls that work in “marketing” and have unlocked black status on the Sweetgreen app. They also work for anyone who rides a motorcycle or has a personal shopper at John Varvatos. For me, I can’t. I don’t own a Harley or a Telecaster.

Still, when done right, a leather jacket can look very cool. The Schott Perfecto is really the blueprint for this stuff. It came out in 1928, introducing us to the signature asymmetrical zipper and large snap-down lapels. It has been worn by every male icon you can think of, from Lou Reed to Marlon Brando to Kanye West to Bruce Springsteen. If you can do it, justice and godspeed. Rock and Roll High School is now in session!

Photo: Courtesy of Vendor

I have always liked a leather version of the timeless, hard-wearing trucker silhouette, like this one from Helmut Lang. The simple cut makes it much more approachable in black leather.

The shearling trimmed leather bomber strikes me as particularly wearable by most guys. It’s cool, but not extreme, and works well in colder climates. The large front pockets can hold your personal effects, and the cut is slightly roomier than a lot of leather styles. This updated version from Mr P. is a slick update on the ’80s classic.

I realized I have no beanies for the coming season. What are some good options outside of the par-for-the-course Noah logo beanie?
Ah, yes, the beanie — or as our friends from Canada call it, the toque. An essential part of anyone’s winter wardrobe. The fit is crucial as we all must avoid the dreaded Saggy Beanie™, popularized by Los Angeles–based club promoters and out of work actors. Allow me to assist.

The well-priced Carhartt has been absolutely murdered by suburban Urban Outfitters shoppers. We must move on. For a simple logo version with a lot of color options, go with some Stoney, bruv. I love it green, but it also comes in orange, gray, and navy.

Keep it traditional with this chunky lambswool cable-knit beanie in oatmeal from Scottish label Inverallan. It will warm your dome during those chilly winter walks on the beach in Nantucket with your father-in-law.

Another cozy-looking option, this pink lambswool number from Howlin’ is the cheerful pop of color we all need for the dreary winter season. It is the perfect shade to garner some grins!

If you are looking to make even more of a statement, this “One Day at a Time” beanie in safety orange from Groveland will do the trick. The color guarantees hunters won’t mistake you for deer while hiking through the woods to observe fall foliage. If you know, you know.

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Ask Chris: My Office Is Business-Casual. What Should I Wear?