First off, full congratulations, Jud, and best wishes to your bride. Second this is a GREAT question... the beach can be a tricky place... almost the Wild West in that anything goes. You probably won't be surprised to hear that my "dressing for the beach" philosophy is pretty much my "dressing every day" philosophy, just... at the beach. Be prepared for a variety of situations, and keep it simple by limiting your choices to just a few (but the right ones).
SHIRTS: First thing I'd do is swap the t-shirt for a shirt with a collar. That'll immediately add lift, substance and even some elegance. I'd grab a couple of pique polos (they've got an open weave, a tennis tail so you can tuck it in or not, plus they come in a bunch of great colors), and a Cuban-inspired guayabera. It's made to be worn untucked and has hem pockets for your phone or keys or a beer. And I'd throw in an awning stripe shirt in the suitcase too - it's got an early-60s California surf vibe - just roll up the sleeves and go.
SHORTS: The length can make or break these... it's why ours have a 7-inch inseam, which still feels casual but looks more tailored than, say, cargo shorts. And I've got your ultimate Bahamas honeymoon shorts fabric right here: seersucker. Super lightweight, with that corrugated texture, so they breathe really well. Most of ours are solid-colored – navy, stone, slate blue - vs. the traditional stripe, so people have no idea they're seersucker until they get up close. We make them with or without belt loops, in case you want to skip the belt. So I'd bring at least a pair of those, and a pair of lightweight twill shorts... maybe stone or fog, or even a light blue or pink.
SWIM: It's nice to see guys abandoning the longer board shorts that dominated the mid-2000s... again, I think a slightly shorter length automatically looks a little neater. We do our swim trunks with either a 4-inch or 6-inch inseam depending on how short you want to go. They're not too torqued-up otherwise: drawstring waist, heavy-duty Velcro fly, pocket in the back, in both Bahamas-style brights (floral, day-glo) and quieter (navy, blue, green.)
SHOES: So I think you want to bring 3 pairs of shoes. A pair of penny or tassel loafers for dinner (also great for the plane,) an upgraded version of your college flip-flops for the beach, and a pair of clean sneakers for the places in between. (I've been into Onitsuka Tigers lately.) As for the beach shoes, my go-tos are a pair of two-strap handmade leather sandals. All-time favorites – I've had the same pair for 20 years. That said, a pair of boat mocs can be cool, too. (I am actually at the beach and wearing them today.)
ACCESSORIES: I carry a tote bag with a zipper when I go to the office, when I travel, and, yes, when I go to the beach. There's this newish one that's a great shape and size, made of very beach-friendly nylon. Inside: sunglasses, a bandana, a few masks, a pen, a notebook, Airpods, and some not-too-heavy reading material. (WM Brown and YOLO Journal are great beach reads, and Magazine B is one of my current favorites.)
SOME COMBOS TO TRY:
For the beach: guayabera shirt, yellow swim trunks, Barbara Shaum sandals, navy tote
For exploring: white pique polo, navy seersucker shorts, OT Mexico 66 sneakers, Randolph sunglasses
For going out: awning stripe shirt, conroy belt, lightweight twill shorts, penny loafers
BONUS ROUND: I'm sure I'm in the minority, but I also still take a pair of pants, a navy blazer, a white shirt, and even a knit tie with me. That way you've got something to wear for an unexpected invite – just throw on the loafers, and you'll be able to say yes to anything.Again congrats on the nuptials, Jud; you're a very fortunate guy. Thank you for your question.
