Summer Shirts for the Long Stretch
Breezy and easy for the time between the Fourth and Labor Day
You don’t have to go too far back in the timeline to revisit the heyday of brands like Gant Rugger and their chokehold on the menswear crowd. From a marketing perspective, they were among the first brands to really embrace digital creators — dropping them in ad campaigns, brand trips, and more. This was, if I recall correctly, during that time where we were post workwear and sort of on the downhill slope of Mad Men mania.

I was not immune to this and fell deeply for any shop that would sell me a madras shirt. So it’s no surprise that after a few years of black T-shirts for summer, I found myself on Poshmark, eBay and Mercari trying to dig up some of those preppy classics. And if Jonathan Anderson’s debut menswear lineup at Dior is any indicator, we may be on the cusp of a prep resurgence.
Truly though, prep never dies. It may lie dormant in Northeastern enclaves (my hometown chief among them) and behind country club gates, but it’s always there just waiting to be set loose among the masses again. The caricature of preppiness is easy to recognize: Nantucket red pants, critter belts, pastel ginghams draped over sunburned skin. Every style tribe can be described in such extremes.
Today, though, I’d venture it’s much more about ease — the kind inherently tied to a carefree (well-moneyed) lifestyle. You’re not trying to become a member of the club, you’re already admitted.
Linen shirts are often championed as the shirts of summer for their light weight. Linen has its place (and I’ll get to that in some other edition) but Madras has supplanted it in our house. It feels lighter with a breathable weave and by nature comes in more engaging prints. In slightly oversized variations, it is the perfect summer shirt. When paired with gym shorts (about all I can stomach to wear in the summer heat) it gives you a kind of scumbag prep look — a far cry from preppy punchlines, but still under the umbrella. Get them while you can still wear them.
Brooks Brothers: In the grander scheme of shirting, this is not subtle. But, on the madras spectrum, it’s a little more subdued than a mix of primary colors and the scale of this plaid is a little more modern than your classic variations.
Beams Plus: On the other hand, there’s this from Beams Plus. The principal bright green is very suited to leisure time and vacations. And truthfully, you could soften it a bit if matched with a suit for a summer wedding.
J.Crew: This is where I’ll caution you about fit. Because we’re dealing with prints that can easily become nerdy (this one especially), it’s best to go a little oversize. Imagine a man wearing this in a super-fitted version vs. one that’s a little boxier and cuts a roomier silhouette. That’s all you need to know.
Alex Mill: You’ll often see madras shirts come in four or five color plaids. That’s typical, but for those who prefer something a little quieter, perhaps even more elegant, there’s this from Alex Mill. (Good sale happening now, too!)
Sid Mashburn: Then again, you could go solid. And with a Sid Mashburn stamp of approval, you can’t really go wrong. (The South is not without its own iterations of preppiness.)
Brooks Brothers: As mentioned, prep doesn’t die. One of its greatest champions, Michael Bastian, who previously designed a capsule for Gant Rugger and his own hyper-luxury brand is currently at the helm of Brooks Brothers. A perfect place to start your search.
Beams Plus: Another subtle pick from Beams Plus and one of the few options that has a fair bit of neutral cream or white in the mix — which can be very useful when trying to pair with a wider mix of pants and shorts.
Polo Ralph Lauren: Similar to Brooks Brothers, you will always find madras worth wearing at Ralph Lauren. (And probably any of those old American stalwart companies.)
Brioni: Last but not least, a linen madras blend from Brioni. It’s sort of a happy medium between the two summery materials. Maybe a gateway or stepping stone, if you will.
Again, the key here is a roomier fit and styling. Do not shy away from a slightly grungier appeal here — you don’t have to wear pleated chino shorts with these. In fact, it’s best to go with something that isn’t so preppy — carpenter denim, gym shorts, etc. I personally go with vintage Umbros and dirty Vans when in the city. But to each their own. And let your chest hair free, of course.
(I had hoped to include some camp collar shirts in this but that will be the next one!)
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I’ll be ordering approx all of these
I was born, raised and educated in Connecticut and prep is in my blood. To me, the only true madras comes from LLBean (maybe Tuckernuck)