When it comes up that I write about style for a living, I’m often asked some version of the following: What [insert clothing article of choice] should I buy?
A better man might answer with something more worldly or interesting — the best shirt is the one you feel most comfortable in — but, sadly, I tend to try my best and throw out something judiciously considered and helpful. Regardless of the retail price, I’m typically met with an exasperated follow-up, post-cursory Google search: Why is it so expensive?
I fully understand this line of reasoning. Putting aside the conversation around how much it should cost, clothing has, on the whole, gotten pricey, especially in recent years. Worse, pricey clothing is not always good, whereas plenty of more accessible clothing is, or at least serves to perfunctorily plug a wardrobe gap.
Still — and this is a hill I will die on — some pieces are worth spending on. As the pseudoscience of cost-per-wear dictates, there are certain features worth the premium many times over; leather footwear and time-tested work jackets don’t come cheap, but they’ll last you forever and look good doing so. (The ROI on a good pair of jeans, for instance, is through the roof.)
I’ve spent the better part of a decade figuring out what’s worth investing in, and what you can farm out to the Gap (no longer a derogatory statement). Below, some thoughts on what in your closet you should (and shouldn’t) spend the money upgrading.
The workwear jacket has been around for centuries in one form or another, but it’s only in the last twenty-ish years or so that it’s really been cemented as the casual layer of choice. That being said, given its recent promotion to mandatory purchase and inherent functionality across three and a half seasons, it’s one of the few areas where I recommend going all in.
There are plenty of quality options to pick from — a chore coat from Le Mont St Michel is forever a solid purchase — but for my money, nothing beats the indestructible, 100% cotton deck jacket from RRL. Ralph Lauren’s rugged sublabel packed the style with all the best bits of the category: a grosgrain weave that stands up to weather and patinas beautifully, a half-lined interior for multi-season use, a workwear look that distinguishes you from the hordes of denim truckers and never goes out of style. $700 is expensive, but for a multi-decade investment, it’s more than worth the cash.
A workshirt may seem like an odd splurge, given that most of us aren’t reaching for a reinforced number at the crack of dawn to assist with a hard day of manual labor. But having a button-up that you can pull on every day of the year, rain or shine, regardless of whether you’re headed into the office or out for dinner, is worth its weight in gold. Wythe’s western-inspired version is particularly unique — cut from a custom-developed tickweave fabric that’s silky and a bit gauzy but built to last for years, it’s got the durability of a proper workshirt without the weight and scratchy feel.
Until recently, I would’ve told you that, given the average amount of wear one gets, T-shirts weren’t worth the extra expense. (It remains the case that — from Buck Mason to Kirkland — there are plenty of more affordable styles out.) Copenhagen-based brand Son of a Tailor changed my mind.
While the brand’s cotton tees are priced at a premium, its highly customizable sizing offers a fit that’s as close to bespoke as an off-the-rack tee can get. Throw in the buttery soft, long-staple 100% Supima weave, and you’ve got a product I’ll happily shell out $75 for.
As a rule of thumb, if you’re pulling on jeans more than twice a week, upgrading to some high-quality denim is a no-brainer. But to tell you the truth, I always tell people the same thing: Put in the work and shop for high-quality vintage in person.
That being said, not everyone has access to a shop that carries orange tabs, and for those who can’t or won’t make the pilgrimage to Sorbara’s or want an entirely personal patina, OrSlow is the next best thing. Created by Japanese designer Ichiro Nakatsu and directly inspired by archival styles, its straight-leg offering is the closest thing to a pair of ‘90s-era 505s I’ve found.
It’s conventional wisdom that leather footwear is one of, if not the, most important purchases a man can make, and while the Paraboot derby is an all-time menswear classic, I’d argue that, in today’s sartorial economy, you get much more bang for your buck out of a simple black loafer.
Historic labels like Gucci and J.M. Weston tend to suck up much of the oxygen around the craftsmanship conversation, but I’ve always been partial to Yuketen, which hand-makes all its footwear here in the States with the best materials money can source. Its casual horse-bit loafer, built with a softer camp sole, offers the most versatile and, candidly, more comfortable option currently on the market.
Sunglasses are a controversial improvement, understandably so: They’re expensive, delicate and very, very easy to misplace. That being said, they’re also a product where the improved version isn’t just noticeably better, but an entirely different experience altogether. (And isn’t that the true definition of an upgrade?) I’ve been wearing the Kinney from California-based Garrett Leight — a wayfarer-adjacent style that’s, like most of GLCO’s offerings, made in Japan and practically weightless on the face — for half a decade at this point: despite having to replace them twice on account of my own negligence, I don’t plan on going back any time soon.
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