What (Not) to Wear on Vacation

The men behind Gilt MANual answer your most pressing style questions.
Photo: Everett Digital

Couldn't 'Brewster's Millions' have purchased John Candy a better beach shirt?

Spring break, beaches–what do you recommend for attire? Linen pants? Flip-flops? What shoes do you wear to dinner?

This is a topic that still keeps me up at night. Why? Well, as a former resident of Hawaii who refused to wear any shirt with a print that could in any way be associated with Jimmy Buffett, tropical formal was at the forefront of my mind. And with a friend’s looming wedding ceremony on Oahu in the summer social calendar, it’s a quandary I’ve begun to revisit. With all due respect to the residents of Honolulu and Miami, the more formal side of dressing gets screwed up so often in hot climates that those missteps become part of local stereotypes. I mean, try not to think of pastel V-necks and billowing white linen when Miami comes up. And Hawaii? Well, they’re called freaking Hawaiian shirts (“Aloha shirts” in the Sandwich archipelago).

The beach is absolutely the only place, in the entire world, where flip-flops (“slippers,” in Hawaiian circles) are okay. That said, I fully endorse sporting boat shoes (waterproof, easily cleaned of sand) or Vans (everything-proof) instead. After a day in the ocean, you will be hungry, and toes in a restaurant is not a good look. Also, avoid baggy, hyper-graphic boardshorts that have more in common with capri pants than swimming trunks. Get something classic from Orlebar Brown or Vilebrequin that hits mid-thigh or two inches above the knee. Another thing, spring breakers—plain, gray V-neck tees. No one needs to know how “Ducking Frunk” you are.

One thing I’ve learned in my return trips to the 808 state is that visitors completely abandon whatever personal style they have back home and sport head-to-toe rayon Aloha get-ups day and night. I can’t stress this enough: Don’t abandon your personal style during a trip to warmer locales. I’d wear exactly the following: a khaki two-button cotton suit (the Ludlow from J.Crew is great place to start), a micro-floral print button-down shirt (Engineered Garments would be my choice; think a subtly-toned Liberty print), boat shoes, and not a sock in sight. In fact, that’s exactly what I’ll be wearing come wedding time.

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