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’ll get you invited back to the beach house.
I’m 29 and turning 30 soon. Currently, I almost exclusively wear navy-blue Vans, mid-calf Nike black socks, Eddie Bauer shorts (not cargos), and Vans short-sleeve button down shirts. What are the essential pieces I should acquire as I move into my golden 30s?
Welcome to hell, baby! I am kidding. Aging is the best. You seem to be wise beyond your years because you are already considering how to dress your age — something most people fail to recognize until it’s too late. Let’s get you outta that Vans shirt, though!
I am a diehard shorts guy myself, but my excuse is Los Angeles heat and lack of an office. We gotta get you in some pants. I recognize your desire for comfort, so I am suggesting you cover your legs with a pair from Gramicci. This style has been around since 1982 and features a built-in belt. They could not be easier.
Like it or not, part of growing up is investing a pair of jeans. Some may overthink this, but you gotta just stick with a classic. This straight leg pair from A.P.C. will work in all situations, and they don’t have any ornate details that would make you look like an NBA player begging for attention.
You aren’t afraid of a button-down, but you have been wearing the wrong ones. You gotta stick with the classic, this blue and white striped mid-weight version from Wythe is just casual enough to wear anytime without looking like an off-duty money manager.
I would like you to introduce sweaters into the rotation. A cashmere crewneck is a must-have, and J. Crew makes some of the best for the price. (Full disclosure: They are a client.) If you want to get wild with color, you can, but this tan is a nice contrast to the usual black or navy.
You will need a blazer and your first one should be affordable; you ain’t ready for the big leagues yet. Thankfully, our friends at Uniqlo have it covered. This two-button number is made with light and soft tweed fabric so it won’t feel too restrictive.
Footwear is where we gotta spend money, chief. I assume you have a job, so start stashing those pennies away for some big boy shoes. The beauty of well-made footwear is that with proper care, it will last forever. Your Vans are still good, but we need something with a sole for all of the important occasions adulthood will bring. This pair of derbies from Tricker’s could be perfect for you. They are handmade, and the suede is a perfect shade of brown. You can dress them up or down. Invest in some eye cream and a good accountant, too. Aging isn’t that bad!
What are some hostess gifts for the holidays besides wine or a candle?
Natural wine is over — so no more $40 overly designed bottles you had to buy from some snob in Silver Lake. Candles will forever be a great gift, but we can push further.
John Derian is a wonderful store in my neighborhood that is chock-full of stuff. A maximalist’s dream, it’s sometimes too much for my tastes, but it is the perfect place for a hostess gift. This set of organza napkins in a perfect shade of blue would make anyone happy. If this color isn’t right, there are plenty others to choose from. Make sure you have them wrap it.
What if we went meta with a book about decorating? This new tome from legendary hostess, style icon, and queen of understated elegance Catherine “Deeda” Blair covers it all: menus, recipes, table settings, and even some charming stories about her life. Perfect!
A modern candle alternative, the humble room spray is often overlooked, and this one from Aesop never disappoints. I wish I could describe it myself, but Aesop does such a good job, so I will just repeat after it: “A union of enlivening florals and Tobacco, Istros stimulates the atmosphere with aromas of the bazaar.” Oh, baby.
As I said, natural wine is over, and you can’t show up with a six-pack of Modelo. Time to graduate to the big leagues. Nothing says “I am happy to be here” more than a simple bottle of Dom. Salud!
I’m the only finance guy at a trendy interior-design firm. Any recommendations on footwear?
You don’t need Margiela Tabi boots to fit in. We can find you some appropriate, cool — but not too cool — footwear options to fit in with your Issey Miyake-clad co-workers.
I am predicting a return of the iconic Tod’s driving shoe. They are low profile, feature no unnecessary bells, and whistles, and can be worn with almost anything. This full-grain leather pair in a nice navy blue would be perfect with a suit or jeans.
The office-ready version of the too-popular Blundstone, these Chelsea boots from Australia’s R.M. Williams are made with a single piece of leather and hard-wearing Goodyear welted soles. They are just dressy enough without being dainty.
If you want to keep it a bit more trad, I love these all-black boat shoes from Sebago. It’s a classic style, but this monochrome version feels more Monday morning all-hands meeting than weekend on the Cape on your father-in-law’s sailboat.
This is probably the best simple white sneaker that can be worn anywhere. It’s been around for 50 years for a reason. I wouldn’t play tennis in these, but I would definitely wear them in a relaxed office setting. For this price, get two pairs just in case.
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