What to Pack for a Tropical Vacation

A mere month ago I was playing on the beaches of Oahu with my wife, my family, and no kids. I love my children, but learning the difference between a trip and a vacation was enlightening. I’m going to have to make it a point to do an annual trip without them and let them get their own mini vacation with grandparents and cousins.

As can be imagined, my typical clothing choices for a March in Salt Lake City are very different from what should be worn in Hawaii. Here’s what I packed, along with what I realized a didn’t need to bring, and what I wished I had.


Left to right from top to bottom:

Nike Trainers: One of my favorite parts of the trip was getting the chance to exercise outside. I played around with bodyweight exercises most days and never pushed myself as hard as I do in the gym, but having some shoes that are great for a workout were still necessary.

Ventoso Driving Shoes: These drivers were a perfect way to dress up a bit without looking like I was on the island on business. When we wanted to go out to eat they were an easy slip on and they were great in the airport. I always recommend a shoe that will come on and off easily while having your fourth amendment rights violated by the TSA.

Hollister Flip-Flops: I’ve owned these for eight years. It’s a testament to how little they get worn that they’re actually still in great shape. I recommend getting something cheap and expendable because you never know when they’ll get lost, stolen, or destroyed.

Cabana e Fogo Swim Trunks: Shorter than most guys are comfortable wearing, but some great trunks. These were my go-to pair last year and I was grateful to have them on the trip.

Bluemint Swim Trunks: A new edition to the wardrobe for this trip. These are some high-quality trunks that fit great, dry quickly, and perfectly straddle the line between too short and too long. What’s the point of working on that quad definition if you can’t show it off?

Taft No-Show Socks: I’m friends with the guy who started this company and he’s done very well for himself. If you’re ever inclined to go sockless (and I highly recommend it) this is the most sanitary, sanity-saving way to do it.

Olivers Apparel Athletic Shorts: Just like the Nike’s above, I wanted a good pair of gym shorts. However, with packing space being minimal, I also wanted something that I could wear when not at the beach. These transition excellently from the gym to the streets and are very comfortable in both environments.

H&M White Chinos: While I do like shorts, there’s something a bit more grownup to wearing a pair of pants. White fits the environment well and communicates some intentionality.

Docker’s Lightweight Alpha Khakis: Because we spent a decent amount of time in locales other than the beach, a second pair of tropical-weight pants was a necessity.

Target Tank Tops: Cheap, fit well, great for the beach, the pool, or a workout.

H&M Black Ball Cap: As tempted as I was to take a Panama hat, I was more active than having that hat would have allowed for. While we spent the bulk of our time on the sand, more of it was used playing frisbee, wrestling, or skim boarding than just lying around, so I wanted a hat that could stay on with the activity.

Forever 21 Oxford Cloth Shirt: Great as an open layer over a tank top, or a little more dressed up when buttoned up and worn on its own.

Forever 21 Madras Shirt: Lightweight and great for exploring on the island when not in the water.

Beckett & Robb Oxford Cloth Shirt: This was my airport shirt. The long sleeves help with temperature regulation on the plane and it worked great with a more dressed-up flight ensemble.

Most of this stuff was picked up on the cheap, and that was intentional. With a vacation like this, especially one with more of a focus on beach time and playing than on museum visits or fine dining, I wanted clothes that I wouldn’t miss if something happened to them. While I do advocate paying the best for things like Staples and dress clothes, there’s always a time and a place for cheaper, lower quality items.

That said, neither my shoes or swim trunks came cheap. Drivers are versatile for so much more than just a vacation and a quality pair of trunks should last a very long time. The great thing about those BlueMint shorts is their quality, cut, and classic styling mean they could be something I own and wear for decades. The cost per wear on a pair of trunks like these is significantly less than replacing cheap board shorts every year.

So what did I bring that I wish I hadn’t?


J Crew Oxford Shorts: Even when using limited space, it is possible to over pack. These didn’t get worn once. I had enough by way of pants and swim trunks that there was no real need.

Jewelry: Man this was a rookie mistake. I have my daily wear of stuff that I figured I’d keep on rotation while on our trip. After the first night, none of this ever left my nightstand until we left. Even when we got a bit more dressed up to go out, it was unnecessary.

H&M Espadrilles: These aren’t great for the beach and fell into the over packing territory for anything else. Any environment in which they would have been worn was better served by either the flip-flops or the drivers.

And lastly, what did I not bring that I wish I would have?


Forever 21 Sweatshirt: Simple. Athletic

MyVice Sweatpants: Simple. Athletic

While the temperature difference between Utah and Hawaii was significant, that didn’t mean Hawaii was without its cold nights. I also learned, the hard way, that spending an entire day in the cold water, could lead to some pretty low body temps when coming back onto land in overcast conditions. Even just lounging around our house at night would’ve been more comfortable and enjoyable with a little more body heat retention.

All in all, I believe I did pretty well. That being said, I know what to include and what to omit for the next trip to make it all the more enjoyable.