I Styled My Brother for a Week, Via FaceTime

I Styled My Brother For a Week, Via FaceTime

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If you really want to get to know somebody, I recommend dressing them for a week. I can think of at least a dozen revealing things you’d learn about me if you attempted such an undertaking. I am already quite familiar with my brother’s sartorial development, and yet talking through his thought process behind getting dressed gave me a new sense of what it’s like inside William Young’s remarkable head. For starters: his favorite color is purple. Who knew? I’ve known the guy since the day he was born, 24 and a half years ago, and I had no idea.

As we prepared for this cross-country experiment—my brother is in San Francisco and I’m in New York—William gave me an overview of how things were going over in his closet in San Francisco by way of an interview. He’d been working on revamping his style in the months leading up to quarantine, and “just as it was getting good,” he had to take his talents back to the confines of his apartment. After our conversation, I received a follow-up phone call while I was watching the new episode of Billions—an activity the subject knew he was interrupting—to let me know that he had “Kondo-ed his closet right before quarantine and now regrets it” and that I could quote him on that.

He told me that a few factors have shaped his aesthetic sense of self: the occasional shopping excursion with the brain trust that is my parents and me, complemented by an ongoing dialogue with his inherently stylish friend Rem Remmel. “Rem has given me good advice: when you’re looking at your closet and see a lot of blue or gray, the trick is to be more intentional with color,” William relays to me. “When you’re shopping, you have to go out of your way to be more adventurous.” William’s also in a dedicated Instagram DM with 5 or 6 guys, including Rem, that’s exclusively dedicated to clothes: “There’s a lot of ALD [Aimé Leon Dore] and PAA, a lot of vintage and secondhand goods, links from Hard To Get and Grailed, a decent number of Birkenstocks—which is when I consider leaving the group. Rem also opened my eyes to Corridor. Oh, look at this tote that just landed in the DM.”

While this headline reads, “I Styled My Brother Over FaceTime for a Week,” the truth is really that he allowed me some agency, but less than was initially promised in our original agreement, and so I had to find backdoor strategies for wielding my influence.

Day One

William tells me that, as a product of moving to San Francisco, he defaults to the same formula: “Every time I go out, I’m wearing a T-shirt with an unbuttoned button-down shirt over it, and I could probably spice that look up—cycle it through with less predictable combos.” The formula is a trusty default for a reason: “It’s as much a climate thing as a style thing—in San Francisco, it’s always 60 degrees outside and 75 degrees inside, so it’s good to have a 60-degree outfit and a 75-degree outfit all baked into one.” To ease into our project, we start with this familiar combination: a green corduroy button-down I helped William pick out in Montreal over Thanksgiving, paired with his “Pleasures” t-shirt.

Day Two

When I asked William if he has any style proclivities that might be women-repelling, he tells me about a tendency he had in the early years of college: “It involved wearing jerseys with plaid so multicolored it clashed with itself, and I rocked these fits with some regularity. I certainly did not know that I was repelling women, and if I could go back to my sophomore year of college, I probably would have asked you for advice.” William demonstrates the jersey/plaid combination above.

With our second outfit, we toe the line of being intentional with color without veering into outlandish territory. It is here that I’m allowed a peek through the viewfinder into William’s relationship with shoes: “Footwear is a funny thing because I don’t wear half the shoes I own, but I constantly want more shoes. My footwear aesthetic for the last 12, 15 years has been strictly basketball shoes… occasionally I will allow a loafer into the mix, or a flip-flop or two in California, but one thing that makes my style unique is that my outfits have to complement a pair of basketball shoes: My favorites are 2010 Hyperdunks, Kyrie 3s, the Harden Volume One. I’m currently wearing the Kobe 1 ProTros.” I tell William I wish we could include a supercut of every time we’ve arrived somewhere my parents would deem appropriate for dress shoes and they look down to see William still wearing his basketball sneakers with an otherwise perfectly acceptable outfit.

Day Three

Here’s another example of plaid that clashes with itself, though as a hand-me-down from our father, the at-times polarizing shirt holds sentimental value. To spiff it up, William and I agreed on this fisherman sweater from Noah, which William bought with a gift certificate I gave him for Christmas last year (one of the aforementioned quiet ways I wielded influence in this process).

Day Four

Here’s an attempt at breaking the mold of T-shirt + unbuttoned button-down, care of this fleece sweatshirt William just bought via the Hard To Get newsletter (I take full credit for introducing him to HTG, and now Blackbird Skyplane), and a genre close to William’s heart: the “event-based shirt.” He and my mom tracked down this Luka Dončić T-shirt at the NBA All-Star weekend, after it appeared to be sold out in his size. He reports that he’s also been eyeing a Grateful Dead-inspired T-shirt made for the 1992 Lithuanian National Basketball Team, from the legendary ‘92 Barcelona Olympics, which launches us into the requisite discussion of tie dye: “I really like it as a concept and find it really hard to wear in most cases that aren’t going to a jam band concert.” We agree that the wash needs to be vibrant and have a certain kind of clarity: a muddy tie dye is unflattering no matter how entrancing it seems in theory.

Day Five

Another attempt to transcend the button-down default. William had asked me, “What can I wear that pairs well for a jaunt out to the grocery store with my face mask? And because my face mask doesn’t allow me to show I’m smiling, what’s something I can wear with the face mask that brings out my eyes?” The answer lies in the unintimidating, light blue rugby shirt: We are both pleased with this Rowing Blazers x Luke Edward Hall rugby (another gift from me).

Day Six

William’s an avid surfer, so we reconsidered the various outfits he could wear or pack in his car for the beach, for maximum logistical flexibility if his presence was requested elsewhere post-surf. Transitioning from this head-to-toe OV look that we bought in the original Outdoor Voices pop-up with my employee discount, this terry cloth polo and loafer combination checked all of the necessary boxes.

Day Seven

We both agree that the red golf shirt is perfectly nice—red looks dazzling against our genetically-similar olive complexions—but to William, it seems to represent a bit of complacency, not challenging himself enough creatively when it comes to getting dressed. His counterpoint, a self-appointed after picture, comes with its own tagline: “Here’s what you wear to the airport when your next flight is in 2021.” I can barely believe he’s daydreaming about traveling for work.

Aside from the conclusion that William’s vintage-to-brand-new ratio in his closet is something I should aspire to, here’s my final takeaway: If you’d like to reboot the sartorial style of someone in your life, I think the most effective and gentle method is slowly chipping away at it, giving them gifts and advice over time, and letting them develop on their own terms, with your aesthetic two cents offered as a guardrail.

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