Ask Chris Black: Cool Ties & Sneakers for 40

Aug 22, 2023

Chris Black (co-host of ‘How Long Gone,’ partner at consultancy Public Announcement) answers our most pressing questions; if you have one, email [email protected] with the subject line “Ask Chris.”

Chris Black (co-host of ‘How Long Gone,’ partner at consultancy Public Announcement) answers our most pressing questions; if you have one, email [email protected] with the subject line “Ask Chris.”

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 thought I was a type-A Virgo perfectionist, but you have me beat. Tie length driving you “insane” is absolutely wild. It’s a minor annoyance at worst. But, you are a teacher, a difficult and taxing job that leaves you tattered and frayed after a long week of shaping the developing minds of future generations, so you get a pass. You don’t need custom ties. You need cool ones.

I love a green tie. Looks great with a blue, white, or even striped oxford. This one, from the London-based tie masters at Drake’s, has a print composed of oval medallions with a little gold and white for brighter colors. It’s hand-rolled and made of pure silk. Even your mouthiest student will give you kudos.

A red tie takes a little panache to pull off. You run the risk of looking like the leader of a young Republican meeting. That being said, this red silk tie with small flowers from Sid Mashburn really speaks to me. The flower pattern is cheeky and fun, and the shade of red is just right.

The knit tie, for some reason, feels very appropriate for a teacher. Personally, I have always found them hard to pull off, but I have a few friends, mainly Christopher Storer and Michael Hainey, who do it right. Regardless, this one from the Armoury comes in a beautiful shade they call rust and would look great with a pair of dark jeans.

Although I hail from Atlanta and have been surrounded by SEC football diehards my entire life, I have never attended a tailgate. For the uninitiated, it’s when people get drunk in a parking lot before going to a (preferably) college football game. It’s a tradition. You can outsmart your peers by simply not wearing a Michigan jersey or flip-flops. A tasteful tailgate look can have a nod to your team’s colors, but you don’t need to paint your face blue and yellow.

Let’s keep it simple on the bottom. A nice, well-made pair of navy trousers from Beams Plus will work in non-tailgate situations too, but they are simple and hard-wearing for game day. The relaxed fit will keep you cool even if the Wolverines blow it in the red zone.

Again, this a shirt for grown-ups, but you can roll the sleeves up if gets a little warm, and you are good to go. I wear one all the time, and the fit is great, perfect for tucking. Undo the button-down collar to feel a little more casual.

J.Crew (whom I work with) collaborated with the Maine-based Rancourt & Co. on a perfect pair of suede camp mocs. This feels like a game-day shoe, not as stuffy as a loafer, not as casual as a sneaker. They will break in beautifully.

The classic logo needlepoint belt might be a bridge too far, but I think it’s a clever way to show your team pride without having to wear a jersey or a hat. Just tuck in your Oxford shirt, and all of a sudden, your allegiances are showing. Good luck this season.

What a good, simple, and pure inquiry. As we get older, our footwear choices have to mature. I don’t want to see a 40-plus-year-old man trying to rock Travis Scott Dunks or any other footwear that requires a raffle to own. I also don’t want to see you strutting in some cooked Brooks or Hokas. Don’t even get me started on designer sneakers. Yikes. It’s a fine line!

I got a pair of these several years ago when they got reissued. They have since been given the Aime Leon Dore treatment, but you should only wear this simple original colorway. It’s the perfect early-aughts running shoe, a classic sporty color combo, and super comfortable.

These are similar to the New Balance suggested above, but brown is a nice understated accent color that you don’t often see on this style of shoe. Plus, Asics are the kings right now!

The Spezial is the underappreciated cousin of the more popular Samba and Gazelle. It has a ’70s feel, and nothing beats a classic gum sole. This colorway, a mix of blues, will work with anything.

This shoe has been overdone by the small-shirt, big-pants crowd, creative directors, and Berlin types, but it is still a comfortable classic. If you don’t fall into the previous categories, then you can easily wear this all-black version as a daily driver.

By submitting your email, you agree to our Terms and Privacy Notice and to receive email correspondence from us.

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.