15 Affordable Menswear Upgrades for Your Next Vacation

Okay, so it's technically $5 over our highly scientific, not-at-all arbitrary price threshold, but given the wear you'll get out of Miansai's bracelet wherever you head next, we'd be doing you a grave disservice not to include it. Pony up the extra five bucks and your wrists becomes a big fit in and of themselves.

Looking to pack light on a warm-weather getaway? Start with these hauraches, which wear like sandals when you need sandals, and loafers when you need loafers.

The best kind of vacation pants move seamlessly between situations. Madewell's roomy linen trousers, for example, will look great in basically any OOO-related context they land in—inside, outside, poolside and everywhere else you'd like to disassociate.

Bucket hats don't have to be goofy—or a Hunter S. Thompson-level commitment. This one boasts a brim big enough to keep the sun at bay, a cool lil' daisy chain around the outside to keep the vibes strong, and will look right at home on a camping trip or one that's decidedly more beach-focused.

In case you haven’t noticed, sunglasses are getting a lot chunkier these days. We’re not mad at all the extra heft—especially when they look like these (expensive) and somehow clock in at under $100.

We're sworn devotees of carefree loose-knit shirts regardless of our OOO plans, but they hit different when you've put some distance between yourself and any rote responsibilities. Abercrombie's vintage-inflected crochet number is as carefree as they come.

Think of Salomon's RX slides as vacation-ready convertibles with off-road bona fides. Or, more specifically, enough sneaker-like elements to handle any rogue physical activity you'll encounter when the primary goal is relaxation.

We love a pair of swishy do-it-all shorts as much as the next guy (hence the Patagonia Baggies below), but we also love shorts that can help you clean up post-beach in a pinch. Shorts that look great with sneakers or leather sandals, hit somewhere around the mid thigh, and are, of course, exceedingly lightweight. Shorts, in other words, exactly like these.

Birkenstocks are some of the best sandals on the planet, but they tend to have a serious aversion to water. This gloriously cushy EVA riff solves that problem, and for those who like to pack options, also weighs basically nothing. (Seriously—you might wanna toss 'em in a bag if it gets windy.)

Fair warning: If you buy this shirt—which is more laid-back than a lounge chair, and far more portable—for an upcoming jaunt somewhere warm, you’ll want to wear it well before you get on the plane. (You should let yourself, by the way. It'll look great with jeans and loafers.)

This might go without saying, but the tote you haul on the subway every day isn't the bag you should bring when you're headed anywhere but the A train. Samsonite's packs down to a crazy-small size, is tough as hell, and features a few convenient zipper pockets as a welcome bonus.

If you normally rock a pricey ticker (or one with sentimental value), pack a cheap, cheery alternative to ensure you're not fretting over your wrist while you’re supposed to be relaxing. At the very least, Timex's handsome, hardy model gives you one less reason to check your phone.

If, for some awful reason, you can only pack one pair of shorts on vacation, pack Baggies. They swim as well as they hike, they're relaxed but not sloppy, and they'll lend your fisherman sandals and Oxford shirts a dose of old-school outdoorsman energy. Packing more than one pair of shorts? You should still pack Baggies.