What men should wear on vacation in Hawaii? Suggested packing list [with photos]

Aloha guys!

Andy here–I make that distinction because Sheila takes care of 99% of the posts on Go Visit Hawaii. However, she’s asked me to share my tips for what guys should pack–and wear–for their Hawaii vacation.

In Sheila’s guide for what women should wear while on vacation in Hawaii, she went over a lot of basics that are good tips for us guys too–casual, breathable, and loose-fitting clothing should be high on your packing list. Specifically for us gents, here are my tips–based on a few dozen trips to Hawaii bringing only carry-on!

On the water/snorkeling

If you plan to be on a boat tour or heading out to snorkel, here’s what I would pack:

While you could keep your SPF 50 sunscreen topped up, being in the water means it will constantly wash away or get diluted. With that in mind, I recommend a long-sleeve rash guard. They are super lightweight, have SPF 50+, and dry quickly. They’ll keep the sun off you and provide a little bit of a layer for when the wind picks up.

Along those lines, a baseball cap will keep you from sunburning your head. The one shown is also quick drying, so I can rinse out any sweat (or saltwater) and it will dry quickly in the Hawaiian sun.

Sunglasses should be polarized with full UV protection. For about 5 bucks, add a retainer–which stops you losing your sunglasses while kayaking etc.

Your swim shorts are your own preference. I prefer a pair with a velcro pocket, so I can stuff a ziploc bag with some tipping money and room key. The shorts above will also look good around the poolside restaurant (see below).

Flip-flops, or slippahs as they call them in Hawaii, are the shoe of choice here. Sand rinses off easily and if they get wet, they’ll dry out in a few minutes.

By the pool/around the resort

The outfit below allows you to quickly go from the pool to the restaurant without needing a change of clothes.

While the fedora may not normally be your style, I find it works well for Hawaii. This one by Bailey of Hollywood is packable and very lightweight.

A white cotton shirt serves two purposes. First, it’s a guys equivalent of a cover-up. For those of us without 6-pack abs, you won’t want to go anywhere without it. It also immediately looks dressy enough for any restaurant in Hawaii, especially the pool side bar or cafe.

Now you can see why I prefer the dressier looking swim shorts. They look great with a white shirt and will fit in well at most restaurants in Hawaii.

Hiking in Hawaii

Hawaii is full of amazing hikes. No matter which Hawaiian island you visit, you’ll likely want to get out and explore a hiking trail. This is what I would wear:

Some key things to note here. First, you’ll likely want to go with something with long sleeves and long pant legs. If not only to keep the sun off, but because mosquitos apparently love to go hiking too, so it saves applying lots of bug spray.

Your shirt should be super lightweight and moisture wicking. If you get warm, you can just roll up your sleeves or open a button or two. I recommend zip-off pants, so if you get too hot you can cool down easily.

Another good reason for bringing zip-off pants? You’ll need long pants for horseback riding or ATVing. They also come in handy on the flight to Hawaii and if you’re departing from, or returning to, colder weather at home. You’ll also appreciate both items if you decide to take a trip to Haleakala at 4am! 😉

Lastly, some sturdy hiking shoes are recommend. While I have seen guys on hiking trails in flip-flops, they quickly regret it if it rains and the trail becomes a slippery mess. The above have sturdy soles and are meshed so they quickly drain and dry out, should I have to cross a stream.

Out to dinner/at a luau

This outfit will work for 99% of all restaurants and bars in Hawaii.

Hawaii is the one place in the world where every guy can pull off a Hawaiian shirt–or Aloha Shirt as they are called on the islands. I bring 2 or 3 different designs. I used to bring half a dozen, but then I realized two things. First, I would only wear the shirt for 3-4 hours at most, so I could easily wear each shirt twice with it getting even a hint of funk. Secondly, you’ll likely want to eat at a different place each night, so no one will notice if you wear the same shirt twice.

My shorts are from the Crazy Shirt store. They look great and have an elastic draw-string waist–which comes in handy after my 5th consecutive night of eating onolicious Hawaiian food!

I’ll mostly wear my flip-flops out to dinner. Pack some that have leather thongs and you’ll look more dressed up than the rubber “slippahs.”

That fancy restaurant

There are very, very few places in Hawaii where I’ll feel the need to dress up a little more than shorts and an Aloha shirt. For those occasions, I’ll break out that white oxford shirt and match it with some Crazy Shirt long pants. Again, elastic draw-string waist for optimum comfort! These trousers are also comfortable to wear on the flights to and from Hawaii.

I’ve switched up the shoes here. Slip ons are about as dressed up as you’ll need in Hawaii and these ones by Patagonia are my go-to favorites. Why? They are meshed and breathable and feel like bedroom slippers. They have a sturdy sole–I’ve even hiked in them–but are definitely passable for those restaurants that frown upon flip-flops.

I hope this has helped those that are panicking over what to wear in Hawaii. Obviously your style might differ from mine, and the above is certainly not the only clothing I’ll bring when visiting Hawaii. If I know I won’t be hiking I’ll skip bringing the hiking shoes etc. See more Hawaii packing tips.

If you’ve read the above advice and still have questions, fire away in the comments below and I’ll do my best to help out.