What to Wear in Hawaii

Hey hey, Fledglings! I’m back to blogging after the honeymoon! I hope you’re all having a great summer and enjoying whatever bodies of water are closest to you.

We honeymooned in Maui, and if you’ve ever thought of going there, trust me on this: Go. There is no reason not to, if you have the resources to get there. The weather is stunning, every view from every angle is breathtaking, the people are friendly, the food is just life-changing…we’re already planning a second trip, that’s how good this is. I’m not normally a fan of repeating trips, because I could travel somewhere new instead, but for Maui? Oh yeah, I’ll go back.

Pictured: Heaven.

If you’re considering hitting up America’s 50th state at some point, you’re probably wondering what you should pack. After all, we’ve already discussed how wasteful oversized-luggage fees are and how we really don’t need them in our lives. Today, you can learn from my experience and minimize your packing, so that you can maximize your snorkeling/swimming/dining/awesomeness.

  1. Don’t stress about looking amazing. We went to some VERY fancy fine-dining establishments, and every one of them had a dress code of ‘resort casual.’ What’s that? It means don’t show up in your soggy swimsuit, but other than that, you’re pretty much fine. It’s an island thing; nobody dresses up. Capris or shorts and a floaty top, or a sundress and flip-flops, are more than fine. For dudes, shorts and a Hawaiian shirt or polo shirt are perfect. There are no suit-and-tie restaurants in Maui – at least, none that we went to, and some of the places we went were hosting wedding receptions. Where all the guests were in the kind of attire I just mentioned. Put your mind, and your wardrobe, at ease.
  2. It’s HOT. Okay, it’s not ‘Texas in August’ hot, but the summer weather in Maui consists of temperatures in the mid-80’s, high humidity, and lots of wind in the afternoons, and you will be out in it. Because of the year-round mild weather, most buildings are open-air to some extent, and the AC in closed buildings is kept mild, not the arctic blast of mainland big-box stores. You’re not going to be comfortable in anything clingy or structured, so dress for maximum airflow with sarongs, sun dresses, and sheer coverups. Learn from me, Fledglings: I went out in leggings exactly once, and I felt like my legs were going to suffocate. Maximum airflow, guys.
  3. Don’t stress about looking ridiculous, either. Are you worried about ‘looking like a tourist?’ Don’t. You’re gonna be surrounded by them, and the locals are going to be dressed fairly similarly. Bright, loud, busy patterns are de rigeur for men and women, so you’re going to feel more out of place in basic black than you will in a bright floral pattern. My advice: embrace the touristy cheese! The brighter the better, who cares? You’re not going to see these people again, and like I said: they’re all going to be dressed like tropical birds too. Oh, you’re sunburned and you feel pudgy? So were we! So was Every.Body. Else. I promise, if you’re doing it right, you’ll be having way too much fun to feel self-conscious, right along with everybody else.
  4. Buy some clothes while you’re there. Don’t bring one outfit for each day. First, you’re likely to spend several days wearing your swimsuit and nothing else, so you can absolutely re-wear your dinner clothes. Second, there are tons of kitschy general stores and tourist stores that sell the aforementioned floral coverups and sun dresses. Go get some of them! Get some Hawaiian shirts and some tank tops that say ‘I ❤ Maui.’ Why not? They’re fun, comfy, and then you can bring them back as souvenirs.
  5. You need fewer shoes than you think you do. Your flip-flops are fine for nice restaurants. They’re fine for the beach. They’re fine for shopping. Really the only things they’re not fine for is jogging and hiking. If you intend to do either of those, bring appropriate shoes, but if you don’t, just bring a couple pairs of sandals! I brought way too many shoes, because I was really ambitious about all the hiking we’d do. We didn’t hike at all. Pretty much all our activities were water-based, and we wore sandals. I had a pair of nicer flip-flops, and a pair of waterproof Teva sandals for the beach, and that’s all I should have packed. Shoes you can hose off are a MUST. You don’t want to track sand into stores and restaurants, but it’s going to cake onto your feet and you will need to use those little beach showers to rinse off, even if it’s just your feet.
  6. Keep one outfit for the flight back. Alllllll your stuff is going to get sandy. Hawaiian sand is like glitter; it just hangs around, no matter how much you wash your stuff. Keep one comfortable, clean outfit in your bag or in the hotel drawer so you’re not sandy on the long flight back.

Packing for Hawaii is really easy, if you don’t overthink it too much. Keep everything light and flowy, buy some stuff there, don’t pack too many shoes. That’s it. Don’t go to Maui to impress anyone or to look like a baller; you’ll have a way better time if you go there to cheese it up tourist-style, to relax, and to take it all in.

Next week, we’ll talk about wedding dress codes, WTF they mean, and how to be a polite wedding guest by dressing appropriately. We’re in high wedding season, and some of this is going to be relevant to your lives. Stay cool, Fledglings!


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