The License to Dress Ridiculously
When life presents the opportunity, take it.
Over the last few years, there’s been an increased emphasis on mixing tailoring with loungewear and athletic gear (I refuse to say “athleisure”) in brand lookbooks, with labels like Aimé Leon Dore and Drake’s leading the way.
Now, I’m a pretty traditional guy, but I find a lot to appreciate about the aesthetic. Sure, wearing sweatpants with a Harris Tweed jacket will strike die-hard trads as heresy, but it’s not so different from the once-radical pairing of chinos and a sport jacket. It’s just that our sportswear generally has grown more casual.
What I find most appealing about an overcoat worn over a hoodie, or perhaps a Barbour paired to New Balances, is the sense of effortlessness it conveys; one thinks of an ex-banker on the UES who’s simply thrown on whatever was on hand to run out for a bagel, and definitely isn’t going to post about it on Instagram.
However, this is where I run into a brick wall with ever putting the blended aesthetic into practice. Sweatpants, sneakers, hoodies, etc., are totally inorganic to my own sense of dress and daily life. If I were to suddenly step outside in my polo coat and sweats, it would be pretty obvious that I’m just trying to effect “a look,” and a ridiculous one at that.
Which is what makes having a legitimate excuse to dress ridiculously such a pleasure.
My first legitimate foray into ridiculousness came in the early months of 2023, when I finally began seeing a physical therapist for longstanding running injuries. To visit their practice, I had to walk about ten minutes to and from the train each way, in New England winter weather.
So, it actually made sense to leave the house in workout gear—in this case, a navy crewneck sweatshirt, gray sweatpants, and white running sneakers—but shield myself in the heaviest thing I own: a vintage camel hair polo coat from Ralph Lauren. Round it out with a red or green cashmere beanie, a pair of leather gloves and a printed silk scarf from Drake’s, and you’ll have a pretty good idea of how I was ambling about Boston once a week for close to three months.
And the truth is, I kind of loved it. With a legitimate excuse to leave the house in sweats and sneakers, I looked forward to mixing in other combinations as the seasons changed, switching it up to a Barbour jacket and baseball cap come spring.
Gradually, my time at physical therapy ended, and with it the era of dressing ridiculously. Only for it to return—with a vengeance—when our son started daycare this past fall, at a center within walking distance from our house.
Tasked with drop-off and pick-up each day (such are the perks of working from home), I had to figure out how I’d dress in the mornings. As I always take my run in the A.M., it made the most sense to just push the stroller in my running gear, and “officially” dress for the day once I’d worked out and showered after.
For those first balmy days of September, I was just a guy in short-shorts and a tank carrying a baby down the street—kind of weird, but maybe not ridiculous. Then October came, and I was a guy in short-shorts and a tank and a Barbour jacket carrying a baby down the street.
Fast forward to December, and the shorts were traded in for skin-hugging running tights and the tanks for long-sleeved merino tops. For warmth above I’d begun wearing the aforementioned polo coat, my donegal herringbone balmacaan, or even a shearling bomber jacket. To finish the full picture, add in the ever-present trainers, a printed silk scarf from Drake’s and a brightly colored cashmere beanie.
It was in such a get up that I returned home from drop-off one morning and received a terse judgement from my wife: “you look ridiculous.”
Yes, I do—and I’m enjoying it immensely, as long as I have reason to.
Cut, Make & Trim
It’s been a spell since the last newsletter, as the pre-holiday deadline crunch and the subsequent merriment put this experiment on a little pause. But I thank everyone for sticking around, and as the kids say, “we’re back.”
In the meantime, I took a trip down to Providence to meet Bao Vu, a fascinating self-taught tailor who established the bespoke business K-Zao. I’m used to covering craftspeople and tailors from afar, so the fact that there was a bespoke tailor firing on all cylinders about a 30-minute trade ride away was too interesting to pass up. I was able to write about Bao and their business last week for Robb Report.
Back in November, the fine folks from Drake’s asked if I’d be willing to appear in a new New York-centric campaign for their Perennials collection (for the record, I disclosed beforehand that I don’t in fact live in New York, but have always popped in when I can). The shoot was a really fun day packed with familiar faces—reminding me of just how tight the NYC menswear scene is—and the campaign has since gone live. Catch me looking very orange.
In other Drake’s-related news, I recently wrote up the conclusions of a year-long search to make the perfect Martini for their editorial side.
This is spot-on. The other day, I walked the dog while wearing pajama pants, hiking boots (but not socks), a peacoat and I don't even remember what else -- maybe a hoodie under the coat? I looked, as your spouse (and mine) would say, ridiculous. But for a half-hour or so, it felt glorious.