Closet Constructor: How to Pull Off a One-Outfit Vacation

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Welcome to Closet Constructor, a weekly series where I (a style editor) help you (a well-meaning person who likes clothes) discover new, interesting and affordable ways to really start dressin’.

I, like a good many folks, am a chronic over-packer. Three pairs of loafers? Need ’em. A full Sergio Tacchini fleece tracksuit for a two-day stint in Cancún? Stuff it in there. At one point, I might have felt some semblance of shame or embarrassment about this fact, but I’ve traveled with enough overstuffed duffles and heard enough stories about peers doing the same to have become desensitized.

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But I don’t need to tell you that traveling with a tonnage of apparel and multiple bags has its pitfalls. The already-shitty travel becomes that much more arduous, for one, and the checked bag fees are no joke. There’s the fear that any souvenirs or holiday purchases might push your already-bulging Tumi over the edge. And worst of all, I don’t even wear half of the things I pack.

The sensible takeaway here is to pack one less pair of jeans and be done with it…but I’m admittedly intrigued by the urban legend that is the inverse, the guy who packs so monkishly light that all of his wares can be easily crammed into a backpack or tote. Just the clothes on his back, a toothbrush and maybe, if he’s really feeling hygienic, a spare pair of boxers. The type of guy your hardened midwestern father claims to be before he chucks the George Foreman in the XL suitcase for the annual trip to Fort Lauderdale.

As it turns out, the one-outfit vacation isn’t as much of a myth as I thought. Menswear legend Aaron Levine recently dropped a Rick Rubin-esque packing list that featured a truly twisted single outfit for an entire weeklong St. John trip. How Long Gone host Chris Black similarly copped up to packing light for a stint at a Jamaica resort on a recent pod, suggesting that a swim trunk and a dusty polo was all he ended up wearing every day. Downright aspirational, if you ask me.

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These anecdotes got me thinking; should one want to attempt the one-outfit vacation for oneself, what’s getting tossed in the personal item? Obviously, versatility and breeziness are of the utmost importance, but specific throughlines between the aforementioned examples really center around two major staples — a pair of sharp swim trunks that you won’t feel self-conscious wearing beyond the pool, and a highly versatile button-down shirt that can dress up for any dinners requiring shoes.

As far as the former goes, my answer has to be Orlebar Brown. The brand’s signature Bulldog short is both InsideHook- and James Bond-endorsed, with a crispy quick-dry fabric and primo side-buckle detailing that really dresses ’em up. Button-downs tend to skew dealer’s choice — the range of preference for size, texture and collar shape are highly subjective — but for my money, Buck Mason’s Breeze Cotton-Linen Work Shirt is one of those rare joints that sits in the middle of the dressy-comfortable-casual-rugged Venn Diagram.

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Two items down. Looks like you still have a ton of tote to play with. A pair of open sandals, or better yet, woven loafers, make sense as a do-all pair of footwear, and some fold-down linen trousers should ensure you get secure a table at even the fanciest Osteria without too much trouble. (If they require a sports jacket, you probably don’t want to go there anyway.) Stuff a hat and however many pairs of briefs you can into whatever modicum of acreage you have left and you’re good to go, chief.

There you have it: the four-piece capsule I’d jet to pretty much any warm-weather destination with if I could ever find the time. You’ll just have to go in my stead — post-closet constructor haul, obviously. Enjoy the weekend.