How to Dress Well Without Regretting It
Not rocket science, but a longevity-minded foundation for your best-dressed self.
When I used to work in a more “fashion-forward” sphere, getting dressed was a much more important part of my life. In that era of style and the internet, there a ton of pressure to have photo taken at fashion week or at Pitti Uomo or something.
If you played your cards right, you could become a micro industry-celebrity. That cache could translate into real opportunities for your career or as a certain type of influencer. (Anybody who says different is lying.) Today, that same pressure is rooted in dressing for likes, etc.
That pressure makes it all too easy to spend frivolously on trend-forward pieces. Of course overindulging in that creates caricatures that trade style for attention. Those attention-grabbing items are still out there, and they pique my interest, but I just don’t have the strength to keep up with it anymore. I don’t know who does. I don’t know who can afford to.
I rely on a few pieces that I’ve had now for years — maybe even decades. The plain truth is I haven’t found anything better to replace them. They’re all pretty timeless and while I refuse to buy into “capsule wardrobes” as a concept, you could think of them in that way. They’re building blocks that can be a blank canvas waiting for an accent, but can also stand as a simple masterpiece. Buy them now, wear them forever, regret them never.
The T-Shirt: Every five or six years, I have to replace my t-shirt arsenal. Designs change, so every cycle I have to do more research. Fit-wise, I like them to be gently boxy for a more forgiving silhouette. Usually I go with a mid-weight for comfort and a sturdy but not wispy drape. I wear these almost every single day. (You can roll the sleeves and then drop them down if you want to style it a little. Or break the neck seams.)
Some notes: There is no universal “perfect” t-shirt, no matter what any magazine tells you. But these three strike a nice balance of weight, proportion and quality. When you’re t-shirt shopping you’ll see tons of materials to choose from. But my advice is to keep it exceedingly simple: 100% cotton is your friend. The more “features” (moisture wicking, etc) a product has, the more it tends to degrade the quality. (This is purely based on my experience).
The Jeans: I know that this is the most basic of basic items, but as I’ve written before, they’re very tricky. One person’s jeans are another person’s nightmare. The pair I’ve found that seems to be almost universally flattering comes from Alex Mill, which I like to think of as a “thinking person’s store.” They’re roomy but not baggy and pay homage to the carpenter pant without being too like workwear. I have white, blue, and black pairs. (Honestly ditto for their chinos as well.)
The Coat: Anybody who has followed my writing knows that outerwear is my weakness. You get more mileage out of outerwear than most other items in your repertoire and the designs tend to be a little more exciting than your other menswear staples. About ten years ago, I went bananas over a coat by Tomorrowland. I still wear it almost religiously and it’s held up remarkably well. It is a quintessential topcoat — long, double breasted, and with a handsome PEAK lapel. The real kicker though, is the material: a Loro Piana fabric with a subtle weave of two shades of navy blue. It will make nearly any man more handsome. A few neutral and timeless optins that are similar.
I can appreciate that these are perhaps higher ticket than most items. But, if there is a place to splurge it is here. A well-styled coat can elevate a hanes t-shirt and faded jeans to vertigo-inducing heights. Also, the Banana Republic camel coat stopped me dead in my tracks. There’s a lot of discussion about brands being “back” nowadays but Banana has been quietly fantastic. Of all of these, I’d get that one.
The Jacket: Shorter jackets — denim or suede truckers, for example — are another important building block. When worn smartly, they provide a layer underneath a topcoat and let you have strike a more casual note and cut a more “rugged” silhouette. Plus, if you’re particularly proud of pants and want to show them off or want to show off your squat legs, they won’t cover the goods the way a topcoat would. My personal preference here is denim, but any version of the below will suit you just fine.
On the resale market, flagging that this Dior jacket is the best denim jacket I have ever owned and it’s rare to find one for sale. It has the added bonus of a nice insulated interior so you can wear it a little more throughout the year. I’d buy it to replace mine if it were my size, but for $210 it’s a steal.
The Oxford: It’s boring, I get it. But an Oxford shirt is becoming on almost every man, provided you’ve got the right fit. I prefer them to be a little more “leisure life at Camelot” fitting, so tend to go for shoulder seams that are maybe half an inch too big and try to make sure the silhouette is a smooth and steady slope when viewed from the side. Sleeve rolls always. It’s anti-purist, but a little stretch in the material goes a long way.
The Sweater: I’ve written about my love of navy blue sweaters before, but of all the things in my wardrobe, these guys work the hardest. You need a good one to throw on with gym shorts on some days or to lounge around your house in. It doesn’t have to be 100% cashmere, but it should be soft. It should have some room but not be too big — you can save the oversized plays once you’ve hammered out your basics. My favorite one is an old Acne 70 Cashmere/30 Wool blend that has a natural texture to it that almost hides any pilling. If you’re looking at full wool sweaters, try to go for something brushed for added softness, or a merino.
The Sneakers: I am a minimalist when it comes to sneakers. My daily life doesn’t require “nice” shoes to wear to an office. I work out in sneakers, I go out in sneakers and I rarely deviate from this course of action. When I do, it’s for loafers (which I’ll get to next). In my opinion, there’s no better option than a white tennis shoe. And if you’re going to do a tennis shoe, best to go with the one made famous by legendary player Stan Smith. Runners up would be the Achilles by Common Projects and the Nike Air Force 1s, both which are just part of menswear canon these days.
I’ll also note that these can be a little hot during the summer, so best to switch them out with a pair of Vans ($80). I buy one pair every year and wear them to absolute hell.
The Loafers: While most of my life is now spent in sneakers, I do rely on a good pair of dressier shoes for the rare occasions where I need a suit. I wore loafers I’ve had for almost a decade to my wedding and sometimes with jeans. The classic is of course the Gucci 1953, but the price has gotten out of control. They were at least $300 less when I bought them — highway robbery! Black is slightly more versatile than brown, but as long as it matches your suit and you can wear it to both a wedding and a funeral you are okay.
This is far from exhaustive and admittedly these aren’t the most exciting pieces out there. But everything linked here has longevity so your chance of regret is…minimal. If you get the classics down, you can fill them out with more trend-forward pieces.
The other thing you have to think about here is styling, which is an art. Rolls, tucks, cuffs, scuffs, wear and tear — all these things add up to a greater sum that lets you add your own vibe to the mix. More on that later, though.
Until next time.
JJ
My favorite common projects story is a man getting dressed down by his wife/girlfriend for wearing them to the Ritz in London for high tea and being denied admittance, meanwhile my boyfriend had worn blundstones and gotten in…
Copy link ➡️ iMessage ➡️ Husband ➡️ “so good pls read”