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’m addicted to Crocs and dad shoes. Upgrade my style but with comfort, please.
Crocs are easy and comfortable but should only be worn when doing light chores around the house. They have taken hold in a way I would never have expected. Everyone wants to be comfortable, but there are better ways than looking like a child at the pool.
Sorry, these (and most of my recommendations) will have laces. Mephisto is a classic “Old Guys Rule” comfort brand, but the Match has been worn in fashion circles for years. They look good, and the comfort is next level. Stick with tan or black textured leather.
One of the best sneakers of all time, I have kept a simple gray pair in my closet for over a decade. The look is simple enough, so they feel more versatile. They also come in several widths if that is something you need.
This style from Salomon is super lightweight and very comfortable. They land somewhere between a shoe and a slide, a hybrid to help you easily wear real shoes without sacrificing comfort.
I am feeling generous, so I will throw you a bone. If you cannot escape the warm hug of a plastic mold, at least wear the only passable Croc. The Dylan Clog is a little mature (you can’t decorate it with charms).
Best oxford shirts for men?
A subject that is close to my heart. I have been wearing oxford shirts since I was a kid and maintain that nothing is more versatile. You can wear one loose and free or tucked in with a tie. Just do your best to avoid looking like a menswear nerd from 2012.
J. Press is as old-school as possible without going to Brooks Brothers. This shirt is made in the USA and has an unlined button-down collar. The regular fit is nice, a throwback to a time before “slim fit” and Untuckit.
First, I love this color. It’s a fun twist on the traditional blue and white I recommended above. Wythe, an emerging New York City brand, has mastered shirting. This is no different. Somewhere between trad and formal, this works for the weekend or the office.
I have this shirt (they are a client) and I wear it all the time. The oversize fit is casual and cool and the color is slightly left of center — best worn untucked with a looser-fitting pant.
I often wear one of these because it’s built like a tank. The Torcas shell buttons are substantial, and the length is just right for staying tucked in without a struggle. It has broken in nicely, too.
My sock game needs a refresh. Any recs?
This is something I have been dealing with lately. We need the right socks for boots and cold weather as winter continues, but not something so thick and warm that it makes your feet sweat. With sneakers, you just want something plain and versatile. There is a lot to consider!
This unfortunately named style from the sock kings at Falke really work with boots. Made from thick (but not too thick) organic cotton, they stay up and come in a wide array of colors to fit your mood.
I got a few packs of these and love them for the gym. The Nike logo is on the front, and the Stussy logo is on the back, a nice and subtle change from the double side Swoosh. This is the best affordable everyday sock on the market.
Simple, soft, comfortable, and durable Smartwool is the real deal. These have a subtle tonal cable-knit pattern and are the perfect all-season weight.
I am not sure, but I love these. Yes, they have a cut smiley face on the bottom, which the brand affectionately calls “happy heels.” I have given and received these as gifts, and they get worn often. They aren’t cheap, but they sure are fun.
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