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.
My husband wants to upgrade from boat shoes for summer casual. What’s a good option?
The boat shoe might be making a comeback. I actually wear an all-black pair from The Row pretty often. But if hubby wants a change, I am here to help! We can keep things in a similar vein but throw in a few wild cards just in case.
He is obviously quite familiar with the boat shoe, but let me introduce you to the canoe shoe. Maine-based Quoddy sews each shoe by hand in a traditional moccasin construction. They slip on easily and mold to your foot over time. The brown pebble leather with the Vibram sole is my favorite.
The Stan Smith is a classic, and this version is made to the original specs out of much more premium materials. They are authentic and easy, like Common Projects, but not corny and expensive.
It’s been a few years — any updates to your Ivy Sport look for summer?
Ivy Sport is a look birthed on the idea that at any moment, you can start a jog or hit the tennis court with a quick footwear change. Preppy but not stuffy. You don’t want to look Equinox-ready. The key elements can shift depending on the weather and your mood. Let’s look at some easy additions to the classic lineup that will work in most summer settings.
I am a known polo wearer. My default is the well-priced Uniqlo two-button. But the long-sleeve polo is underrated. The originators at Lacoste do it well, especially in this shade of green. It works with shorts or pants, and if the temps rise, pushing up the sleeves looks just as cool.
Doek has been making shoes in Japan for 140 years. This oxford is more substantial than a classic pair of Vans and comes in this perfect Ecru shade that will age well over time. Worth a little extra money. I could hit a few forehands in these if I had to.
A high-end wedding gift for the creative couple with no registry?
I am leaving this week for a wedding in Italy and the couple in question hasn’t provided a registry, so this one hits close to home. I like to lean into something useful but luxurious, something they will have for a lifetime. An envelope of cash works, but we can do better.
Using this thing properly will take a little time, but giving the gift of espresso to the newlyweds seems like a no-brainer. It looks amazing on the counter, and if they are true coffee drinkers, they will use this every day and think of you. Imagine waking up to a double-shot almond-milk latte in bed; that’s true love.
If the couple in question likes to partake in a celebratory glass of Champagne on special occasions, this set of flutes from Baccarat will be the perfect gift. Sleek, sophisticated, and handcrafted, I can hear the cork popping now!
This print from New York–based artist Dike Blair would look great in anyone’s home. The photorealistic drawing depicts a couple of hot dogs and a can of Coca-Cola, a little slice of Americana. As a gift, it feels special and well considered.
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