Figuring out exactly what kind of clothes you’ll need can be tricky…especially if it’s a place you’ve never been. Well don’t worry friend…I’m practically an expert when it comes to figuring out what to wear in Hawaii.
Sundresses, rompers, floppy sun hats, cute sandals, you know the drill. So whether you’re lounging around a cabana poolside, hitting the beach bar, or having a nice dinner, around the resorts and resort areas are where you’ll see people the most “dressed up” in Hawaii.
If you’re snorkeling from the beach, you don’t really need anything special, but mostly I get asked about what to wear snorkeling when going out on a snorkel excursion on a boat. Here’s my routine: I wear my swimsuit, a pair of quick dry shorts, a long sleeve rashguard, and flip flops when I show up.
I don’t think you need “hiking boots” or shoes or whatever they’re called. Hawaii is not exactly a hidden destination and most of the best trails are pretty heavily frequented and maintained so you don’t need real heavy duty footwear.
If you’re planning to go up to Haleakala (Maui) or Mauna Kea (Big Island), you’ll need to dress warm, especially if you’re going for stargazing or for sunrise since it’ll still be dark when you go up.
If you’re just out and about around the island, sightseeing and what not, you’ll want to wear clothes that are cool and comfortable.
Most restaurants in Hawaii are pretty casual (and even the nicer ones it’s okay to wear nice shorts and a top), but I usually like to wear a cute sundress and sandals just because it’s fun.