By Trip Styler, on March 15, 2016

Style guide: What to wear on Maui

Spoiler alert: You don’t need to pack much for Maui (or any Hawaiian island)! With a 75°F average and year-round sun, what to wear in the tropics is as easy as throwing a dress or an aloha shirt over your bathing suit.

As a former overpacker, I used to spend way too much time agonizing over the right hat, dress, or shade of lip color for every getaway. After a three-hour stint attempting to select the “right” clothes, I’d get frustrated, find the biggest suitcase in my home, and throw everything in. Fail.

Yet, what to wear in Maui has never baffled me because the island has no fashion pretense or “scene-y” dress code. People wear what’s comfortable—I know a few locals who don’t even own pants—which is a testament to the Valley Isle’s casual, come-as-you-are culture.

After 20-something trips to Maui’s sugary shores staying in every kind of lodging from basic beachside apartments to posh properties, here’s how I suggest you pack for Maui from top to toe with style, speed, and savoir faire.


Ball caps for the beach or wide-brimmed hats for the pool work wonders at providing shade from Maui’s constant rays. I usually pack both—one for jogging or hiking, the other for lounging. Word to the wise: Consider a hat’s fold-factor to avoid toting extra things in transit that won’t fit into your case (such as a structured straw hat). My biggest chapeau consideration, aside from fashion and function, is that it has to fit in my carry-on, which is why I favor caps with enough spring to handle being crushed in my suitcase.

What to pack: two hats.


Whether you’re traveling for five days or two weeks, my top tropical-themed packing tricks are:
1) Pack more tops than bottoms (ladies: this rule applies to tops or dresses).
2) Four days of outfits yields enough mix-and-match potential for any length of trip.
Since you’ll be in your bathing suit most of the time anyway, you’ll only need a few tops to get you from your stay to the sand by day, and another set for nighttime outings. As a starting point, look at a long oversized button-up as a plane top that converts into a chic pool cover-up. Otherwise, a few tank tops and T-shirts are a sure “fit.” Men: In addition to the casual tops mentioned above, three short-sleeve, linen, or lightweight chambray dress shirts will suffice.

What to pack: one oversize button-up shirt for plane-to-pool, a few tank tops, and T-shirts (men: two or three dress shirts and T-shirts).

What to pack for maui


Ladies: Dresses are the easiest garment to bring to the tropics because they’re an all-in-one outfit. For daywear, flowy frocks can be worn to breakfast, to the beach or pool, or out and about. When the sun dips down, opt for something cinched, structured, or sleeveless to amp the wow factor.

What to pack: three flowy frocks and three structured cocktail dresses. 


Since the tops and/or dresses you pack will do the heavy lifting wardrobe-wise, go light on the bottoms. A pair of casual denim shorts, a pair of sleek shorts (or skirt), and a pair of pants—preferably the ones you wore on the plane—are all you need. And yes, you did read that right; I only mentioned three bottoms. Remember: Your bathing suit will get the most mileage in Maui.

What to pack: casual shorts, sleek shorts (or a skirt), and a pair of pants.

Viewfinder Tip: Once you’ve selected what to pack, lay it out to see everything in context, do one final edit, and then place it into your suitcase as if you’re laying bricks.


Flip-flops, or “slippers” as Hawaiians call them, are considered everyday footwear—so common they can be worn to casual restaurants (unless you’re headed to an upscale eatery in Wailea or Kapalua). Shoes take up the most real estate in your suitcase, so edit, edit, and edit again when it comes to selecting the right pairs. Thankfully, flip-flops barely make a dent in your packing density, so bring two pairs. Otherwise, a gorgeous and multipurpose pair of neutral sandals are a solid “sole mate,” and if you want to hike or jog, throw in a set of sneakers (bonus points if you can wear them on the plane to save space in your bag).

What to pack: one or two pairs of flip-flops and standout sandals (men:  opt for loafers, canvas espadrilles, or cotton slip-ons instead of sandals).


While I never suggest overpacking, feel free to go crazy with bathing suits because they are compact. Other than this, undergarments, belts, sunglasses, a scarf for AC, a wee amount of jewelry—but never wear it in the water—and toiletries round out the accessories you’ll want to complement your top-to-bottom threads.

What to pack: bathing suits, undergarments, belts, sunglasses, a scarf, jewelry, toiletries, and a good beach read.

Et voilà! You’re ready to hop aboard the Pineapple Express without the packing stress.

What garments do you pack for a tropical trip?