In 2018, I spent four days in Positano looking like a grease fire. I had bought this ‘luxury’ resort shirt from Ted Baker—it was a navy floral print, very ‘vacation vibes’—but it was a 100% polyester blend that felt like wearing a Ziploc bag in a sauna. By 11:00 AM, I was dripping. I remember sitting at a cafe near the water, feeling the sweat pool in the small of my back, watching some guy in a simple, rumpled white shirt look perfectly cool. I hated him. I hated my shirt. I ended up buying a basic cotton tee from a tourist trap just to stop the itching.

That trip broke something in me. I realized that 90% of what brands market as ‘resort wear tops’ is actually just overpriced plastic designed for Instagram photos, not for actual human bodies existing in 90-degree heat with 80% humidity. Most of it is trash. Total garbage.

The linen lie and the 145-gram rule

Everyone tells you to buy linen. ‘It breathes!’ they say. ‘It’s the fabric of the Mediterranean!’ they shout. Well, I’m going to say it: I might be wrong about this, but I think most linen tops suck. Unless you are spending $200+ on high-grade European flax, linen feels like wearing a burlap sack that’s been soaked in starch. It’s scratchy. It wrinkles the second you look at it. And honestly? It’s not even that cooling if the weave is too tight.

What I mean is—actually, let me put it differently. It’s not the material; it’s the weight. I’ve started weighing my vacation shirts on a kitchen scale before I pack. I’ve tested about 12 different tops over the last three summers, and I’ve found a hard rule: A resort top should never exceed 145 grams. Anything heavier than that is a jacket, not a shirt. If you’re looking at a ‘heavyweight linen,’ run away. You want something that feels like it might float away if a light breeze hits it.

Real resort wear shouldn’t feel like a costume. If you feel like you’re playing a character in a movie about a guy who owns a boat, you’ve already lost.

I used to think linen was the only way. I was completely wrong. Now, I’m a total convert to Tencel or high-twist cotton voiles. They don’t have that ‘I just slept in a dumpster’ look that linen gets after twenty minutes in a car.

The part where I get petty about brands

I have a specific, probably unfair hatred for Orlebar Brown. I know, I know. Every style influencer treats them like the holy grail of resort wear. But I bought one of their Terry toweling shirts—the ones that cost like $175—and I looked like a giant, depressed Muppet. It held onto water like a sponge. If you actually go near a pool in one of those, you’re carrying five pounds of chlorinated water around your neck for the rest of the day. Never again.

And don’t even get me started on J.Crew’s recent ‘Giant Fit’ obsession. I tried one of their camp collar resort shirts last month. I’m a medium. I put it on and I looked like I was wearing a sail. There was enough fabric in the sleeves to start a small colony. I understand the ‘boxy’ trend is in, but there’s a difference between a relaxed silhouette and looking like you’re wearing your dad’s clothes from 1994. It’s lazy tailoring disguised as ‘fashion.’

If you want something that actually works, look at Portuguese Flannel. Their Tencel shirts are incredible. Or Alex Mill, though their sizing is a bit of a gamble. I own three of the same cream-colored cotton-silk blend shirts from a random boutique in Greece I found years ago. I don’t care if they aren’t ‘on trend.’ They work.

How to actually pick a top without losing your mind

When you’re shopping for resort wear tops, stop looking at the patterns. Patterns are a distraction. They’re how brands hide cheap fabric. Instead, do these three things:

• The Light Test: Hold the shirt up to a light bulb. If you can’t see the silhouette of your hand through the fabric, it’s too thick. You will die in the Caribbean heat.
• The Button Check: If the buttons are cheap, shiny plastic, the shirt is probably trash. Look for mother-of-pearl or at least a matte urea button. It sounds snobby, but cheap buttons usually mean the seams will rip after three washes.
• The Collar Construction: A ‘camp collar’ (the flat one) is the only acceptable choice. Anything with a stiff, button-down collar at a resort makes you look like you’re about to give a PowerPoint presentation on quarterly earnings.

Anyway, I digress. I once spent an entire dinner in St. Barts trying to subtly unstick a cotton-poly blend shirt from my chest with a butter knife. It was the most humiliated I’ve ever felt in a public setting. That’s the stakes here. It’s not about ‘style,’ it’s about survival.

I know people will disagree. Some people love the weight of a heavy linen. Those people are probably lizards who don’t sweat. For the rest of us, thin is king.

Is the ‘Matching Set’ thing over?

I’m seeing a lot of guys wearing the matching shirt and shorts combo. The ‘cabana set.’ I have a very strong, very biased opinion on this: unless you are under the age of 8 or currently on a movie set playing a 1950s mobster in Havana, don’t do it. It’s too much. It looks like pajamas. You walk into a hotel bar wearing a matching pineapple print set and everyone knows exactly how much effort you put into ‘looking effortless.’ It’s a paradox that fails every time.

Keep the top interesting. Keep the bottoms boring. That’s the whole trick.

I still haven’t found the ‘perfect’ shirt. I have a closet full of 7/10s. Maybe that’s just how it is. We spend all this money trying to find the garment that will finally make us feel relaxed, but relaxation is a state of mind, not a fabric blend. Or maybe I just need to stop buying clothes from brands that spend more on their Instagram ads than their stitching.

Buy one good white Tencel shirt. Wash it by hand. Don’t overthink it.