These looks run from an aloha shirt over casual shorts to linen pants at dinner, and from athletic wear on the trail to swimwear on the beach.
The day’s plan decides which one you wear: sand, trail, pool and restaurant each ask for different fabric, and athletic wear in a synthetic blend beats cotton on a wet trail.
Pack by the activities on your schedule, then add the pieces that cover the evenings, where linen pants and an aloha shirt do most of the work.
1. Aloha Shirts
Matching prints work better than they sound: keep the same navy base and let the pattern do the talking. Pick a shirt with a dark ground and a mid-size print, so it reads as a shirt rather than a costume.
Wear it open over a white undershirt or buttoned at the top with chinos. For women, the same print works as a shirt, a dress, or a wrap.
2. Casual Shorts
Shorts that land at the knee are my pick for a Hawaii trip, since they look like something you would wear on any weekday. Dark navy or charcoal keeps them easy to pair with a patterned or solid button-down.
Loafers and a baseball cap finish the look without effort.
If you are shorter, a hem just above the knee keeps your legs from looking cut off. Skip anything baggy past the kneecap.
Wearing a crochet matching set in Hawaii exudes the kind of vibe that perfectly complements the island’s laid-back atmosphere. The breathable fabric allows for comfort in the hot and humid climate, so you can feel as good as you look.
3. Athletic Wear
Hiking days call for a black tank, a pair of shorts, and a cap worn however keeps the sun off your face.
Black hides sweat and trail dust better than light colors, and a sleeveless cut gives your arms room to move.
Choose fabrics that feel light and dry quickly.
Cotton gets heavy near a waterfall, so synthetic blends are the better choice for wet trails. Pack the tank in your day bag even if you will not hike.
4. Swimwear
Bring at least 3 swimsuits, because a wet pair never dries fully overnight and putting one on damp is miserable. Rotating them also keeps the look from getting stale across a week of beach days.
A bold palm-leaf print is the fun choice, and it works best when the rest of the outfit stays solid.
Pair it with one plain solid trunk in navy or black for days you want to look quieter. Briefs show the most skin, so choose a fit you feel at ease in.
5. Linen Pants
Wide-leg white linen pants are the best answer to a warm evening that cools off. The loose cut lets air move, and the fabric breathes better than cotton twill.
Layer an open light blue long-sleeve shirt over them, as above, and add leather sandals. Linen wrinkles, and I think that is part of its charm, but hang the pants in a steamy bathroom before dinner.
Keep the top and bottoms in the same light family, and let the shirt carry the color, or the outfit gets fussy.
What Not to Wear
Heavy denim is the first thing to leave at home. Jeans and denim jackets run hot and heavy in Hawaii’s humid weather, though denim shorts can work depending on the season you travel.
High heels are the second.
Most days involve the beach, the pool or a trail, and pointed heels fit none of them. If you want some height, a small wedge handles sand and grass far better.
Chunky white sneakers are the third, and they mark you as a visitor faster than anything else in your bag. Sandals or slip-on shoes such as espadrilles are more comfortable and more practical.
Loud, flashy outfits are the last thing to skip. Casual is the norm, so dress comfortably and keep it relaxed.
Packing Essentials
Start with sun protection, since the climate is hot and humid. Pack reef-safe sunscreen, a wide-brimmed hat, sunglasses with UV protection, and aloe or after-sun lotion in case you burn anyway.
Shoes need a plan. Pack one pair of flip-flops or sandals for sand and strolling, and add sneakers or trail shoes if a hike is on the schedule, since slick lava rock and red dirt punish thin soles.
A light jacket or sweater earns its space in the bag, because evenings run cooler and the air at higher elevations can turn chilly fast.
A tote or small backpack handles the day’s gear, from sunscreen and a water bottle to whatever you pick up at the shops.
Skincare and haircare belong in the suitcase too. Humid heat is hard on both, so don’t count on finding your usual products.
A loose cover-up, like a linen shirt or an open camp-collar, lets you walk off the beach and straight into a café without changing. Keep a few breathable tees and tanks for daytime, plus a smaller bag for nights out.
Frequently Asked Questions
What are some good outfits to wear to Hawaii?
Start with an aloha shirt in a dark navy base and a mid-size print, worn over a white undershirt or buttoned up with chinos.
A dark ground stops the shirt from reading as a costume, and on warm evenings I like wide-leg white linen pants with sandals.
What should I not wear in Hawaii?
Leave heavy denim, high heels, chunky white sneakers, and loud flashy outfits at home. Denim is the one fabric I’d leave at home, since jeans and jackets hold heat in the humidity; denim shorts can pass in cooler months.
Pointed heels fit none of the beach, pool, or trail days, so a small wedge is the better choice. Sandals or espadrilles beat bulky sneakers for comfort and for blending in.
