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**nicholascrawford** · September 29, 2012, 06:29 PM

Congrats!

Dress for yourself. You're on vacation and will never see these folks again. Also don't buy clothes for one trip (save for the Arctic, that's kinda specialized). Some colored shorts, prophylactics, sandals or boat shoes, a pair of khakis or chinos, prophylactics, a cotton sweater or sportcoat for cool evenings/dinners, some short sleeves, swim trunks. Nothing too complicated! Wear what you're comfortable wearing! If you're hiking a volcano or doing a tour inside Kauai (wish I had), bring hiking boots and pants ready for the trail. If you're sticking to the beach, sneakers may be the most substantial footwear necessary.

**LesserBlackDog** · September 29, 2012, 07:16 PM

Hawaii is pretty easy to dress for. Much easier than, say, the French Mediterranean. It's absurdly casual. Anything nicer than floral board shorts and a tank top is considered business casual. Bring a bunch of shorts (flat front, slim fit is best... if you don't have any, check out the Target clearance rack) and some polo shirts, simple t-shirts, and maybe a lightweight button-up for evenings out. Fit is more important than formality. The polo shirt alone will make you more dressed up than 95% of the people you'll see. A lightweight rain jacket isn't a bad idea and can do double duty as a windbreaker in case you head to higher elevations. If you plan on doing a lot of sightseeing, you will quickly discover that the leeward and windward sides of the islands can have DRASTICALLY different climates and weather patterns. It's not a bad idea to prepare for rain and wind.

Pants aren't a necessity unless you're on the Big Island and planning on trekking to Mauna Kea or Mauna Loa. Even the visitors' center, 4,000 feet below the summit, is breezy and a lot cooler than sea level.

You should definitely plan on bringing a pair of $5 flip flops (or, in Island-speak, "slippers"). Or else buy some once you're there.

When I was in Hawaii earlier this spring, I brought way more shoes than I needed - boat shoes, canvas sneakers, running shoes, Chaco flip flops, Chaco sandals. The only shoes I ended up wearing were my running shoes (for jogging and hiking) and my flip flops (for everything else). Stylish? Not especially. But, when in Rome and all that.

As far as sunglasses go, something inexpensive from Target will probably suit you in the short-term. No point in blowing a big chunk of cash on sunglasses if you rarely find yourself needing them. A $25-30 pair of Fort Knocks or Mile Highs from Knockaround will get the job done and you won't have to feel bad if you lose them, break them, or never wear them again. A pair from American Optical will be a little more expensive, but good quality and classic style for a lot cheaper than comparable Ray-Bans or Persols.

**kidsampson** · September 30, 2012, 04:16 AM

Thanks for these suggestions. This helps a lot and it's good to hear from folks who have been there, especially recently. With the kinds of clothes I will be packing, it seems like I can pack pretty light (especially with shorts and all). It will also be good to get some last extended mileage out of some of my summer wear I picked up near the end of the season, as it's already cool enough where I live for sweaters and long sleeves.

As for sunglasses, I can't seem to find any my style. I went through 5 pairs of Warby Parkers through their try at home promotion and another pair of Ray-Ban Caravans, but none really fit the bill. I'll check out your suggestions and try to find an end-of-summer sale on some cheap sandals / flip-flops (might be some good filler).

**Johdus** · September 30, 2012, 04:16 PM

Get a pair of linen (or linen-blend) pants that aren't Hammer Time genie style and you'll look better than 90 percent of the dudes out there.

I kopped a pair at H&M for $20 before heading this summer to Bermuda where formality is still the rage.

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