We’re here to help you plan Hawaii vacation outfits for any activity!

Do you look forward to vacations but hate packing? The night before your flight, you’re standing over an empty suitcase, wondering about the weather, how to dress, and what you’ll be doing. 

Don’t let the pressure of Hawaii vacation outfits dampen your pre-trip excitement. Check out all our info below so you know what to pack, where to shop, and how to plan for Hawaii’s weather. 

Hawaii Outfit Tips 

Before we get too far, let me say this: I love planning outfits. Clothes are fun to me, and vacation clothes are even more fun. I love to feel comfortable AND look camera-ready during a tropical hike. I pull out my brightest and most colorful outfits for time at the resort. And layering for microclimates is an exciting challenge. 

But we’re not all like that – I get it. And even fashion enthusiasts can stress over vacation outfits. I’m here to help!

Before we get into the weather and create a packing list, let me offer up a few tips that will help you feel confident as you load up your suitcases. 

#1 Start Packing Early

You don’t want to be scrambling the night before as you realize that your only pair of comfortable shorts has a big hole in them. Or the swimsuit from last season doesn’t fit right now. 

Start packing a week in advance. That way, if you need to make a last-minute shopping trip, you aren’t doing it totally last minute (like the night before your early flight). 

#2 Try on Outfits as You Pack 

If you’re traveling to Hawaii in the winter, you may need to try on some of your summer clothes to make sure they fit. This will also help you pack full outfits instead of an assortment of pieces. Instead of packing 6 shorts and 6 shirts, I try on a full outfit together: top, bottoms, and everything in between. 

That way, when I’m enjoying a relaxed vacation, I’m not figuring out what goes with what. I’ve already tried it on, like the way it looks, and am ready to go. 

#3 Separate Your Hawaii Vacation Outfits

I have this as #3 because I’m going in chronological order, but really this is my #1 packing tip. 

If you’re going on a vacation, separate your full outfits into ziplock bags. 

This helps save space when packing AND keeps clothes organized during your trip. No more rummaging through your suitcase, wearing the wrong layers, and ending up with fewer clothes than you thought. 

I put my underwear and socks in the bag with my outfits so that once I’m in Hawaii, I don’t have to put any thought into the day’s outfit. 

#4 Plan for a Wash

If I go anywhere for more than 4 days, I plan to run a load of laundry. This is especially important now that I have kids who go through clothes SO fast. But even if you’re just managing your own Hawaii vacation outfits, this could simplify your packing. 

Wear the same outfit for your arrival and return flights. Don’t stress over tons of socks. Enjoy wearing your favorite shorts twice during your trip. 

If you give yourself the chance to do a load of laundry, you’ll save time and space as you pack your suitcase. 

Hawaii Vacation Outfit Packing List

Ok, I’ve shared my top packing tips, now it’s time for you to know exactly what to pack. Everybody has different plans for their trips, but here’s what you’ll likely need while in Hawaii:

• Swimsuits – at least 2 
• Swimsuit cover-up
• Hiking outfit – something comfortable that can get messy 
• A rain jacket – just in case!
• Comfortable, light clothes for Hawaii driving tours and sightseeing
• A light jacket or sweatshirt for cooler microclimates or chilly air conditioning
• A heavier jacket and long pants IF you’re going to Haleakala or Hawaii Volcanoes National Park
• A nicer outfit (resortwear) for each nice dinner or lunch out
• Comfortable layers for your flight back home
• Flip flops / sandals
• Sneakers / walking shoes
• Underwear and socks, and all those other essentials
• Pajamas

Choosing What to Pack

Not sure how many clothes to pack for your Hawaii vacation? An itinerary will be the ultimate guide. Your itinerary doesn’t have to be exact, but it will give you an idea of how many times you will likely go swimming, hiking, or to a nice restaurant. 

Many visitors will check the weather before their Hawaii trip, which is definitely worth the time. But don’t worry about checking in again and again. Temps here are pretty consistent, and rain is rare. Plan for low eighties in the winter and high eighties in the summer – and lots of sunshine year-round. 

Another way to know what to pack? Consider what you enjoy wearing. If you enjoy style and fashion, feel free to strut your stuff in Hawaii. But most people here dress casually and comfortably. So bring along the clothes you like to wear, and you’ll feel at home during your Hawaii vacation. 

Do You Need to Buy New Outfits for Hawaii?

If you live somewhere that sees true summer temperatures, then you likely have everything you need for a Hawaii vacation. 

Of course, if shopping for vacation is a fun activity for you, then this is a good excuse to get some new outfits. A fashionable resort outfit, a new swimsuit, or a comfy pair of hiking pants could be just the thing to help you feel confident and fun while you’re here. 

But don’t feel like you need to spend a lot to prepare for your trip. 

Shopping for Vacation Outfits in Hawaii

Hawaii has great shopping. You can go to Walmart or a department store for any forgotten essentials. Or you can pick out a new favorite outfit at a local boutique. 

If you enjoy shopping, here are a few things you might like buying while on island:

• Aloha wear, like a floral print shirt or dress – get this at Walmart, a souvenir store, or the Aloha Stadium Swap Meet. 
• A tshirt from your favorite activity or town – get this in local souvenirs shops or the activity’s check-in area.
• Upscale resort wear from a local boutique – Hawaii’s small towns often have locally owned boutiques with unique items (plus you’re supporting local!).
• Sandals or flip flops – you can get some from Walmart or local surf shops
• Swimsuits – these are fun to buy at surf shops and local boutiques

FAQs About Hawaii Vacation Outfits

Still have questions? We have answers! You don’t want to be guessing about what to wear during your Hawaii vacation, so we’ll help you plan for a fun and fashionable trip. 

Does it get cold at night in Hawaii?

I’ve found that it rarely gets uncomfortably cold at night in Hawaii. It’s still a good idea to bring long sleeves or a light sweater along. You MAY need it in the evenings, but you’ll likely need it for air conditioned stores and restaurants. 

Can’t I just buy my outfits in Hawaii?

It’s definitely possible to buy your vacation outfits once you arrive, but you could end up wasting precious vacation time shopping. So don’t sweat any forgotten clothes, you can get something to wear here. But try to arrive fully packed, so you don’t end up stressing over clothes when you could be lounging by the beach. 

What does resort wear mean?

Some nice restaurants in Hawaii require resort wear as their dress code. For men, this is a button up shirt with slacks or nice shorts. For ladies, it’s a floral dress, skirt, or jumpsuit. Think lightweight, breezy outfits that still look dressy. 

What is an Aloha shirt?

An Aloha shirt is a button up shirt with a floral or tropical print on it. On the mainland, these clothes are often called “Hawaiian shirts.” In Hawaii, we call them Aloha shirts. 

Alohawear includes dresses, shorts, and other pieces in the same tropical or floral print. 

Do I need to pack a suit and tie?

You’ll rarely see suits and ties in Hawaii, and you likely won’t need it in Hawaii. For nice dinners, an Aloha shirt or other button-down shirt will work fine. 

How do people dress in Hawaii?

You’ll see all kinds of outfits in Hawaii. Vacationers are typically in comfortable shorts and shirts, and residents wear something similar during any downtime. Around your hotel, you’ll see swimsuits and relaxed coverups, alohawear, and casual outfits. 

Men in Hawaii will wear swim trunks during any casual activity, and I like to layer a swimsuit under my outfit if there’s any chance I’ll want to take a dip. 

Trip Planning

Focus on your Hawaii vacation outfits, not the logistics of travel! Let our team of local Hawaii travel agents help you plan a vacation full of fun and adventure. We have easy-to-book packages, custom itineraries, and budgeting tools to help make planning a breeze. 

So pack a swimsuit and flip flops and get ready for an amazing Hawaii vacation.