How to Dress for A Week in Hawaii: 4 Essentials

Dancing Feet

What kind of day are you planning?

Comfort is the key to keeping feet happy while on vacation. Footwear may seem like the last thing on your mind, but considering we spend much time walking on vacation, it makes sense to consider it.

Flip flops are available at several island stores, so don’t worry if you don’t have them to bring.

They offer comfort and are seen as acceptable footwear in most places. Hawaii doesn’t have a foot dress code, but it does involve some common sense.

Sneakers and sandals are always on the list of must-haves. If you plan on hiking, appropriate footwear is essential and a requirement for most tour operators. Leave the high heels back at the hotel on these days.

Some type of footwear suited to dinner at a higher-end restaurant would be next in line. If this is not your thing, leave them behind.

Our feet are essential; they carry us around all day without much consideration. If you are bringing new shoes that are not worn in yet, it may be wiser to go pack the ‘old faithfuls’ instead. Foot soreness and blisters are no fun on vacation.

From Top to Bottom

T-shirts and polos seem to be the older of the day, and for good reason. They are cool, are non-restrictive, and allow you to change in and out without issue. Both men and women are happy to wear t-shirts without too much bother, and as a bonus, they are light in your luggage.

Cotton is always the first choice as it breathes better than synthetic fabrics. Short sleeve shirts are a good choice for warm days, and ladies, bring out those linen tops and loose blouses for their sheer comfort every day.

A dress shirt for those special nights out will be handy, as you may feel underdressed if attending a particular event or resort function.

Now, what would a top be without a bottom?

Probably a good way to receive a tap on the shoulder from the local constabulary and a few grimacing looks from your stunned fellow travelers, but if that’s your thing, good luck with it.

For the rest of us law-abiding citizens, shorts seem to be the way to go. Bike pants and leisurewear are good items to take but loose-fitting and comfortable goes without saying.

A word of warning. If you are a pocket person, don’t take shorts that don’t have them. No one likes a complainer on vacation.

Know yourself.

Long pants for those cooler nights (yes, it does get cool sometimes) are always ideal, especially if you feel cold.

If you plan to hike in rugged areas, you may benefit from a pair of chinos or jeans as a cover for your legs, as many find the bushland settings aren’t as tame as expected.

Swim, Be Free

Water sports, swimming, or simply paddling through rock pools will have you reaching for the bathing costume within hours of arrival.

Choose your favorite and pack it as soon as you remember. Leave the ones at home that are uncomfortable or are saving until those extra winter pounds are gone. (it’s ok...we all have them.)

Comfort is paramount when relaxing. Choose board shorts and light shirts as cover-ups if uncomfortable walking around in a bathing suit. 

Drip-dry shirts, rash vests, and dedicated swim clothing are perfect for taking. They dry overnight and are ready to go when you are.

For surfers, a wet suit is mandatory.

Warmth In the Tropics

Regarding packing for the weather changes, you will likely need to bring a light jacket or sweater, depending on your planned activities. The nights can be cooler than the days, so it's best to be prepared if you are out and about.

Hawaii’s weather is mild throughout the year with seasonal variations, and just like everywhere else, it is subject to unseen weather patterns.

This is the tropics, after all, so don’t be concerned if you’re taken by surprise some days.

Seasonal changes aren’t like the mainland, and although it will snow in the highest mountain ranges during cooler seasons, most visitors won’t see it. Rainfall in Hawaii is not uncommon, but the tropical rain is quite different from the cold torrential downpours many of us have experienced.

Pack for warm conditions with sea breezes. Water sports will see you getting splashed on and feeling the cool water on your feet, so bring appropriate footwear if perpetual boating is your idea of paradise.

Some Tips

For those over-packers among us, we may find the suitcases a little lighter simply because heavy coats or snow gear can be left back home in the closet.

Preparing is a good thing. You never know what’s around the corner.

Here are a few other things to consider when packing for Hawaii.

• Choose Easy Care

Clothes that don’t need to be ironed are always winners when on vacation. Choosing clothes that are easy to care for and can be washed if required without needing a dry cleaner or laundry service will save you time soaking up the Hawaiian atmosphere.

• Accessories

For a night out, you may want to pack jewelry and any adornments you can’t live without. Don’t forget the sunscreen and sunglasses or they will be your first purchase on arrival. For those who wear eyeglasses or contacts, consider taking a spare. Things happen.

• Leave Some Room for Dessert

Make no mistake, you will find clothes you wish to purchase as a memento of your trip. Packing less or taking a larger suitcase with room for gifts and your now favorite Hawaiian shirt is a smart way to travel.

• Things That Hold Your Stuff

Carry bags are important as plastic bags aren’t allowed in Hawaii. Choose light fanny packs or totes to hold wallets, beach towels, and all your precious souvenirs.

Plan your chosen activities and what you know are a must-do during your stay.

A little bit of thought goes a long way. Pack dressy casual for the nights and holiday wear for the days. Coupled with light jackets and smart footwear, you will be all set for a week in Hawaii.

Ready to go? Let us show you the best of the Hawaiian Islands for your next stay. Visit us for the best advice and activities suited to you. Plan, book, pack…and go!