Lost Password?

A password will be emailed to you. You will be able to change your password and other profile details once you have logged in.

What to Wear in Hawaii: Tina’s Guide to Hawaiian Chic & More

read about what to wear in hawaii for vacation outfits

by Tina Boomerina (Christina Gregoire)

What should you wear in Hawaii? Well, there are no hard and fast rules about what clothes to pack for your Hawaiian vacation, but after you’ve been in the islands a while, you’ll develop a feel for what outfits work best. So, I'll try to explain my thoughts about what clothes will make you look chic and what clothes will make you look like a Haole tourist dork.

Tip: You don't HAVE to wear an aloha-print shirt or muumuu, but you'll look perfectly acceptable if you do.

what to bring to hawaii for holiday vacation outfits

Pack a Long Sleeve T-Shirt or Hoodie

Bright Hawaiian prints that feel out of place on the mainland look fabulous in the intense light of the tropics.

All I ask is that you and your spouse don't wear matching aloha prints... There’s just something weird about seeing all those older couples in matching aloha-print shirts and muumuus walking down Kalakaua Avenue together. I guess that’s how they find each other if they ever get separated. (Of course, those couples are usually wearing matching red sunburns, as well... but they won’t notice THAT until they get to their hotel rooms to freshen up for their early-bird buffet dinners.)

Yes, I’ve Lived in Hawaii:

What do I, a Seattle native and current resident of Eastern Oregon, know about muumuus and aloha shirts? Well, I’ve lived on Oahu twice, once in Kailua and once in “town” (Waikiki). Also, I’ve been to the islands so many times on so many vacations I can’t count them all.

My first trip to Hawaii was a stay at the pink palace (the Royal Hawaiian Hotel) at the age of four or five. I’ve seen the old Polaroids of myself in a baby-bikini and a little grass skirt. And, that's the only reason I “remember” that first trip. All the rest of my jaunts to Oahu are one big blur.

What to Pack Depends on Location:

I’ve been to several of the outer islands, but the only ones I’ve spent any time on are Oahu and Maui. However, I know as much as almost anyone about what clothing looks right in Hawaii.

Hey, any person who's explored Hawaii knows that people are more laid back in windy Kihei (Maui) and rainy Hilo (the Big Island) than they are in high-density, nightclub-packed Waikiki. Oh, in case you don't know, Waikiki is basically a neighborhood of Honolulu. Waikiki refers to the small, touristy part of the city where most of the big hotels are.

Well, except for the five-star resorts (with their own little worlds... that I know nothing about), you will want "comfort" to be your mantra while packing. Hawaii is always warm to hot, depending on what part of the world you're coming from, so you should bring a lot of loose, casual clothing.

Local Girl Kay Kerns Says: Pack Something for Rain:

While it's often hot, you should remember that the weather changes all the time in the islands. Former local girl and current Boomerina, Kay Kerns, offers this tip,

  • “When it was cold or rainy in Hawaii, I used to wear long-sleeved t-shirts or a sweatshirt. A lightweight cardigan is good too, or a light rain jacket with a hood. A friend who still lives in Hawaii says it rains more now."

Thanks, my friend, for the tip! I always think of the sunshine and I probably should remember to pack a hoodie or a rain poncho the next time I go... I hope I go back... it's so beautiful in Hawaii with all the tropical flowers making the air smell like perfume... and the beautiful beaches... sigh... daydreaming... need to find a way...

And, you're so right, Kay, I know there's a 50/50 chance I'll see some kind of rain, but I've never brought a sweatshirt or cardi with me. Duh.

*** Note: Kay grew up on Oahu, so we should probably listen to this smart chick. If enough of us beg, we might be able to get her to tell us her favorite beaches and the other things she knows about the island.

If you don't have anything that fits right or looks right, don't worry. You don't need to spend a lot of money to get the right clothes. And, we won't tell if you wear the same couple of comfy outfits over and over.

Even if you bring fancy duds, I'm tellin' ya... you're only going to wear the stuff that feels good.

Outer Islands and Most Places:

You'll want to go low-key, Hawaiian-style casual (something like flip-flops and shorts or a floaty beach dress) in places like Hilo and Kauai. I think the vibe is a little more hippie in the small towns of Kihei and La Haina, so break out your Birkenstocks and your most comfortable boho caftan or your softest, washed-out denim.

Your swimsuit, plus a tee (for a guy) or a pareo (for a girl), and a pair of flip-flops (slippers) will take you to 97% of everywhere during the daytime and 73% of everywhere at night... on any island. (If you're old and flabby, you may want to disregard this statement and kit yourself out at someplace like Hilo Hattie's... with a comfortable muumuu or aloha shirt.)

what to wear in hawaii and what not to wear... i think can't remember what i wrote

These Outfits Will Take You Almost Anywhere in Hawaii, With the Exception of the Swimsuit

If you're staying in Waikiki, things are a little more urbane. You may even have a chance to get all decked out in a slinky dress or a "real" suit jacket, depending on your plans. But, even in the "big city", you're still in the tropics, so outfits are pretty laid back compared to the mainland. Guys wear aloha shirts to "white collar" office jobs downtown. Women don't wear heels (or nylons) unless it's a job requirement. Yes, women sometimes wear heels for a big night on the town... or maybe that's just me... trying to look taller and thinner.

Casual comfort is the norm EVERYWHERE in Hawaii... and, that's the way we like it.

tips what to wear in hawaii & tropical cruise

Yes, Yes, No: Hawaiian Shirts

Anyway, I’m going to make some generalizations that will help you look a little more like a “worldly jetsetter” than a “lost tourist”. And, I think these generalizations will help you “fit in” on any island.

Of course, there’s no way you’ll pass for kama’aina (a Hawaiian resident who grew up on the mainland), but you don’t want everyone to think you or your man are provincial Haoles who've never been outside of Wichita.

Does it Really Matter if You Wear the Wrong Clothing?

No, it does not really matter if you have the perfect vacation outfits. You could wear summery mainland clothes and you'll survive.

Everyone will know you’re a tourist no matter what you wear… but what kind of tourist?

Hey, you'll have a great time in Hawaii even if you're wearing old rags. But, if you have a choice between a cute outfit with the right "feel" and some other outfit that looks a bit too "mainland", you should pack the outfit that makes you look tropical (or bohemian), so you'll look perfect in your Facebook photos... right?

I mean, the locals won’t care what you're wearing (especially if you're a teenage girl in a bikini) as long as you are nice (it’s called the “spirit of aloha”) and as long as you tip when appropriate. Hey, Hawaiians often work two… sometimes three… jobs to survive in paradise. But, you'll never understand what I mean unless you've tried living there, yourself. I don't know how people with families can afford it.

Well, Hawaiians and other locals may not care what you wear, but I do (somewhat) because you represent all mainlanders.

And, I have spent much of my life “people watching” in Hawaii (and elsewhere), so I can often spot different types of tourists by their attire. The following stereotypes are mine. They are NOT the opinion of anyone who works in the Hawaiian hospitality industry! So, let me know if you think I’m wrong… because I’m just a bystander watching things from the “outside”. And, as always, stereotypes and generalities have many exceptions.

Don't Be an Ugly Stereotype (Tourist):

Californians: Tourists from California usually wear nice, up-to-date, resort wear from better brands. And, Californians are, in my opinion, the best dressed, most beautiful people in Hawaii, with the exception of the locals, who have their own natural charm. However, the other thing I've noticed, on occasion, with Californians is their attitude of entitlement. If you're from L.A, you may need to learn how to relax. You don't need to be pushy in Hawaii. It will all work out... even if it takes a few extra minutes. Just breathe deeply and get your mind on Hawaiian Time.

Midwesterners: Tourists from the Midwest somehow seem to fade into the background. However, you can usually spot the males by their black shoes and white socks (or white shoes and black socks), which make a perfect counterpoint to their perfectly creased shorts. The hipper heartlanders sometimes wear white socks and sandals... well, at least they’ve got the sandal part right. And, women from the Midwest often wear summery tops and fitted dresses with small floral prints, which makes them look uptight and ill-at-ease in tropical Hawaiian climes. (In case it's unclear, you should try to avoid most of these Midwestern-tourist looks. Aloooooooo-ha!)

Pacific Northwesterners: Tourists from the Pacific Northwest usually try to fit in with the island look, but Northwest natives are not known for their fashion sense… so you never know what they’ll wear. Anyone who’s severely underdressed (and it’s hard to be underdressed in Hawaii) is a possible suspect. However, you can always spot recent arrivals from Seattle and Portland by their ghostly white skin… and their penchant for lying on the beach until they turn into rock lobsters.

aloha print shirt men hawaii what to wear

Yes, Yes, No: Hawaiian Shirts

Easterners: East Coast tourists seldom undertake the long, 10-hour flight from New York to Honolulu, but it’s becoming more common as potential visitors hear about the beautiful beaches, the non-humid climate, the cooling tradewinds, and the wonderful “aloha spirit” of the local people. Women from the East Coast can sometimes be spotted by their white or pastel capris, although this look is also worn by retired Southerners and Arizonans. And, a dead giveaway that a man is from New England (or a one-horse town) is his short-sleeved plaid shirt... which usually looks all wrong in Hawaii. If you must wear plaid, wear a bright or faded Madras plaid shirt like the California surfer dudes wore in the 60s. (p.s. I’m not talking about the males of the hipsteristic persuasion because you guys have your own set of rules.)

Anyway, locals are used to tourists (from the Mainland, from Japan, from China, from everywhere on earth) clogging up their roads, taking over their favorite beaches, and driving up the prices of real estate… but without the tourists, locals would have no jobs.

Well, I guess my point is that you should try to look like you are vacationing in Hawaii rather than a cabin on Lake Michigan. And, of course, you should not laugh when locals speak Pidgin English, especially if you’re talking to one big Samoan. You are a guest on their island, after all. And, you'll pick up what they're saying after a while.

Relax… be nice… have fun. You’re in the most beautiful place on earth.

Well, on to more info about the types of clothing you should pack.

read about aloha print beach clothes

Multi-Tasking Beach Clothes

Tropical, Casual Hawaiian Chic:

They say that Hawaii is warmer in summer than in winter. Bah! It’s always warm and tropical unless you go up in elevation (Haleakala on Maui, the mountain on the Big Island). I mean, when I lived in Hawaii, I would get cold when it went down into the low 70s, but you won't get cold... unless you're really old and skinny and you're always cold.

You might, however, get wet.

It seems like almost every part of Hawaii gets a quick sprinkle or two every day. Sometimes you even get downpours that are like walking through a (fairly warm) waterfall. But, don’t worry. You can walk through those torrents by taking off your shoes and wading through the streets as necessary. You may be dry by the time you get where you’re going or you may be soaked, but either way it’s no big deal. And, that’s because…

...the main fashion look of Hawaii is windblown and casual.

plus size resort & cruise wear

Plus Size Clothes for Hawaii Vacation

Windblown Casual Fashion:

You never know what the weather will do. And, you should never care what the weather will be… it’s Hawaii! I’ve seen it rain for three weeks in November. I’ve seen it when it's totally dry. I ALWAYS have a good time whenever I'm in Hawaii... no matter what. Showers at any moment… no big deal. You can always go upcountry if the beach is soaked.

With that unpredictable weather in mind, unless you’re going out clubbing (maybe), you should forget straightening (or curling) your hair, you should forget the hairspray, and you should remember your younger days when you embraced the natural look. Because, unless you never go outside (and what fun is that), your hair is going to do its own thing. And, the creases in your trousers are history. So plan accordingly and try to get a wash-n-wear haircut. Or pull your hair back in a ponytail or make a bun and hold it in place with a pencil or a chopstick.

Women’s Clothing for Hawaiian Vacations:

Look for clothes that embrace wrinkles… or that don’t wrinkle. Remember that casual casual casual is normal. You don’t have to wear old and sloppy stuff, but easy-to-pack, loose-fitting, casual dresses and shorts – or pants - outfits are perfect for women… especially if made of a natural fabric like silk or cotton. Polyester is a possibility but it can stick to your skin and heat you up… although I’ll admit to wearing polyester in Hawaii quite often and living to tell about it.

evening dress resort tropical vacay

You Can Dress Up if You Want

I never get cold in Hawaii, but some women like to wear a cotton cardigan or a lightweight jacket when eating at an open-air restaurant on the beach at night. And, there’s a good chance you’ll be doing that.

You can wear beach dresses almost everywhere during the day (with or without a swimsuit underneath). The shoe of choice is a pair of flip-flops (cheapo brands or fancy rhinestone styles) because you’re never too far from a beach. Any kind of slip-on sandal is good, but closed shoes get sand in them. Teva-style sports sandals or sneakers are good if you’re going hiking. Shorts and a tee are always fine. And, you can stash everything you need in a beach bag… get the idea?

Even if you hate swimsuits, you should bring at least one. You WILL wear it... even if you only go for a dip in the pool… because you’re afraid of waves and sea turtles. And, a swimsuit cover up is an absolute necessity. I like pareos (big scarves tied into skirts) and sarongs (big scarves tied over the chest like a strapless dress). If you don’t have anything fancy, you can always tie a big beach towel as a sarong like the locals do. (Tip: Towels are easier to wrap when damp.) And, don’t forget to pack a hat, sunscreen, and sunglasses... obviously.

You can dress up a bit more in the evening if you want to, but you don’t have to. Heck, you can wear a caftan or a muumuu to almost any restaurant. (I look better in sundresses, so that's what I usually wear.)

If you have plans to paint the town, starting at a swank restaurant like the ones I mention in the next section, you’ll want to pack an elegant (slinky?) dress, which you can wear with nice flats, wedges, or high-heeled sandals… depending on your balance after drinking a few glasses of wine. Sequined and beaded evening gowns are a bit too much (in general), but no one will ever turn you away for being overdressed.

You might want to read about resort or smart casual for cruises because high-end restaurants in Hawaii are similar.

read about resort wear

Don't Tuck In Hawaiian Shirts

Casual Men’s Clothes for Hawaii:

Men love Hawaii because they get to dress like six year olds... like that ding-dong Charlie Sheen in his bowling shirt and shorts.

Yes, you can wear shorts, a tee (or an aloha shirt), and some flip-flops almost anywhere in town. If you'll be hiking, you might want to pack Tevas or tennis shoes. And, of course, you'll want to pack a few pairs of swim trunks. (Not Speedos. Speedos will make you look like a crazy Sicilian, so wear regular trunks that can pass for shorts.)

The real-life, traditional, Hawaiian male outfit of shorts, Hawaiian-print shirt, and flip-flops (or leather sandals) will take you almost anywhere, any time of day, except for the fanciest of fancy restaurants and a few dance clubs. Personally, I think you should wear long pants at most dinner places and at most clubs... but I'm not you... and I'm not young... so I could be wrong.

Restaurants With Dress Codes:

Many good restaurants have a “resort casual” dress code for dinner. I don’t think any restaurant requires a tie, and unless someone tells me otherwise, I wouldn’t even pack one. The most common dress code for men usually consists of:

  • Shoes (This means no flip-flops, but nice leather sandals, slip-on boaters, and sometimes sneakers are okay.)
  • "Collared" shirt (This means no T-shirts, but aloha shirts are fine.)
  • Long pants (Khakis are fine.)

Most places just don't want you to look like you dragged yourself in from the beach.

read about travel clothes tropics

What to Wear to Dinner in Hawaii

High-End Restaurants With Dress Codes:

If you're the last of the big time spenders (my husband is not) and you have reservations at a high-end joint, such as La Mer (long-sleeve shirt, slacks, dress shoes, jacket... which they may provide), Alan Wong's, Michel's (I've been there), or Hoku's (at the Kahala), I would check with the restaurant or with your concierge.

Resort casual means different things at different places. And, some restaurants don’t enforce their dress codes to the letter as long as you and your chickadee look well heeled… but don’t sue me if I’m wrong. (Notice that they seldom have to tell women what to wear.)

Other than those few exceptions, almost all summer clothes (except for plaids IMO) are perfect. You may want a windbreaker if going out on a catamaran, and you should bring a hat or baseball cap and a pair of sunglasses.

Aloha Prints for Men & Women?

Not everyone wears aloha-print clothing, but I've never been anywhere (including swank restaurants) where Hawaiian prints weren't allowed. Men and women, both, wear lots of florals. It just feels right.

Just in case you don't know what aloha prints are, they are usually bright patterns of palm trees or palm leaves or pineapples or hula girls. And, they almost always have hibiscus (or orchids or plumeria) in the pattern somewhere.

If you don't like Hawaiian prints, try these:

  • Plain Colors: Bright blue, fuchsia, red, light pastel, white, or navy dresses, shirts, pants, tunics, and shorts are always chic in the tropics.
  • Black: Black is perfect for women's swimsuits and slinky dinner dresses. Black slacks and/or jackets look a bit stuffy on men (to me)... although you won't be turned away.
  • Asian Prints: Any type of Asian print (Oriental for those in London) looks fabulous in Hawaii. Typical motifs include bamboo, birds, lotus, chrysanthemums, cherry blossoms... and you can usually find outfits where the print is just a subtle component of the look.
  • Ethnic Prints: Batik, paisley, ikat, and some tribal prints look great in Hawaii.

Well, even if you have to wear plaid, you HAVE to go to Hawaii. There's so much to do... hike in the jungle, lie on the beach, sip a Mai Tai at sunset, snorkel at Molokini, surf the North Shore... or just fall in love while some local dude with a ukelele sings, "I want to go back to my little grass shack in Kealakekua, Hawaii".

Main Things to Remember: Don't overpack. Make sure your clothes are comfortable. Stay casual... and have the time of your life. Aloha wau ia Hawai'i.

More Articles for Chic Women Travelers:

Best Sites for Women's Travel Wear: Wrinkle Free Clothing

How to Look Chic in a Bathing Suit

Best Brands for Apple Shapes -- Women Over 40, 50, 60

What to Wear to a Beach Wedding: 8 Tips for Women Guests

resort wear

Main Photo: Hawaiian Clothing

Photo Credits: Prshots.com. Many of these outfits, but not all, are available. Some are on sale, though not available in all sizes.

  • Main Photo: DorothyPerkins, M&Co, East, M&Co, LongTallSally.
  • Pack a Long Sleeve T-Shirt or Hoodie: X-two.com.
  • These Outfits Will Take You Almost Anywhere in Hawaii, With the Exception of the Swimsuit: WhiteStuff, LaRedoute, NewLook, LongTallSally, Asos, Asos.
  • Pack This, Not That: East, Asos, Apricot, Asos, Apricot, Veramont. (None of these dresses would be BAD to wear in the tropics. I'm showing what I think is better.)
  • Yes, Yes, No: Hawaiian Shirts: Debenhams. If unavailable, try Tommy Bahama, Nordstrom, or Macy's.
  • Multi-Tasking Beach Clothes: M&Co, M&Co (skirt if pull it down, dress if pull it up), Asos (beach kimono or wrap for evening).
  • Plus Size Clothes for Hawaii Vacation: Evans, Joe Browns Plus, Evans.
  • You Can Dress Up if You Want: Asos plus.
  • Don't Tuck In Hawaiian Shirts: Debenhams.
  • What to Wear to Dinner in Hawaii: Asos, Lipsy, LaRedoute, Evans.

What do you think of this article? I may have ruffled a few feathers, but no one else seems to tell the real story about what to wear... so I try my best. Tina

Share on Google+0Pin on Pinterest1,577Email this to someoneShare on StumbleUpon0Share on Reddit0

Tina Boomerina (AKA Christina Gregoire) is a Baby Boomer born at the end of 1952. Her mission is to make the internet a kinder and gentler place for Baby Boomer women around the world. Tina's specialty is fashion for women over 50.

Follow Me on Pinterest Follow My Boomer Lifestyle Blog on facebook

Related Posts

2 Comments

  1. Tina-Boomerina

    Kay, if it doesn't make you too homesick, I would love to hear about what you like to do in Hawaii. I should have had you write this whole article... what was I thinking?

    Tina

  2. Veronica

    Loved your article it was a big help, I didn't know about your tip about us eastternes and our capris. (CHUCKLE) What about white jeans or shorts?