Resort wear collections are a way for brands to keep new product coming to the shelves for customers to buy, and to justify bringing out warm-weather stuff in January. I’m not the type to fly south to a beach somewhere in the winter, so resort collections have always seemed silly to me.
But in early October, I went to Jamaica to stay on a resort for 12 days with my family, and I had to think through what I was going to wear. Suddenly a resort collection made sense! As a style conscious guy, what do you pack for an itinerary of being in the pool or spending time on the beach?
Here’s how I answered that question.
3x Zip-Fly Swim Trunks
Three was enough to rotate between, rinse off, hang out to dry, then wear a couple days later.
I don’t think I can go back to swim trunks that simply pull on. J.Crew used to sell these under the name “Pool Short,” but it seems they haven’t made them in a year or two. I have a pair from Abercrombie, too, but I see no reference to those anymore either. Perusing the Internet I see Land’s End has some called the “Sunset” Swim trunk. The high-end brand Orlebar Brown makes them for $275. And Kent Wang makes them for $75.
Slim white stretch jeans
I traveled in a pair of stretch white jeans, and ended up throwing them on often throughout the week when I didn’t want to wear shorts. Mine are from American Eagle but they don’t have any that aren’t pre-destroyed. Here are some from Todd Snyder.
4x Linen button-up shirts
Button-up shirts are convenient to put on and take off when you’re not in the pool. Linen is a no-brainer (two of them were technically cotton-linen blends). The restaurants on-site at the resort we stayed had a dress code, requiring a collar on your shirt.
Christian Kimber cotton-linen bengal stripe | Spier & Mackay light blue cotton/linen shirt | Spier wide-stripe cotton-linen | Spier reverse-stripe linen | Spier cotton/linen bengal stripe linen | Spier houndstooth linen
4x Polos — three long-sleeve, one short-sleeve — and 4x tee shirts
In the evenings after being finished at the pool or the beach, sometimes it’s nice to just pull on a polo shirt. For those dress-code-required restaurants, a polo shirt sufficed; for me, a long-sleeve polo feels elevated, a little extra cool. Mine were the shirt-collar style, with one fancy “Lupo” polo from Eidos. I packed a handful of tees to throw on when poolside or when spending time in the room. Kent Want short-sleeve navy polo (not in stock right now but black looks great too) | Kent Wang long-sleeve “rugby” polo in navy (and one of mine was white) | Prologue HK one-piece-collar (similar to my Lupo polo)
Tan linen suit and mid-blue cotton-linen trousers
I wore the suit jacket or full suit everyday for a daily service (we were there observing a biblical festival). Spier & Mackay tan linen/silk suit | Spier cotton-linen trousers
Navy espadrilles and tan Sperry boat shoes
I sort of regretted this, because while my boat shoes are very comfortable, the color didn’t go with the tan suit trousers. Which meant I had to wear the navy espadrilles to not feel like a rube with the suit; but espadrilles with a suit is definitely a “look”, one which I embraced but it wasn’t quite thought-out for me. If my boat shoes were a darker brown I’d have been fine. These Sperry’s would’ve been fine (mine are lighter but now sold out) | Ropey Soles royal blue espadrilles (mine are navy but those appear discontinued)
The Watch—Seamaster 300m (Casino Royale 2220.80)
I planned to take my Aqua Terra (ref. 231.12.42.21.01.002) because I was expecting to receive the Omega OEM bracelet I’d ordered for it in advance, and I felt it would be the ideal all-around watch for the trip. It’s dressy, but sporty. Ideal, really. (Read more on that in my Aqua Terra post). But the bracelet didn’t come in in time, so I took my blue Seamaster 300m. And that was probably the coolest choice anyhow, since parts of Casino Royale (in which this reference was worn by Daniel Craig as Bond) took place in Jamaica, and indeed the original Bond novels were written by Ian Fleming in Goldeneye. And it dresses up perfectly fine, too. Omega Seamaster 300m 2220.80 (ebay saved search)
For any future trips, I’d probably add an extra shirt or two in each category. I packed only with a carry-on, and even with that restriction, I think I could have fit a little more if I needed to. We had to do some laundry for several things, but given the casual hang-out-in-the-pool nature of the trip, it overall went well. In the end, the family had a great time, we spent lots of time with good friends, and we returned refreshed having made great memories.
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