What to Wear to Hawaii

by Kirsten on April 17, 2010

HawaiiIn light of my trip to Hawaii in a little more than a week, I thought it would be a great time to kick-off my “what to wear to” posts. Over time I will post about various destinations, complete with items you must have with you, as well as some suggestions on where to buy them. Hawaii fits the bill of a typical tropical destination. Rarely do you need to be concerned with cold weather – a perfect reason to pack lightly.

Hawaii’s average temperature hovers between 75-85 degrees throughout the year. Formal attire is very rarely needed, and resort-wear is what you will find most people wearing. The key to not having to check your bags is smart packing. Most women (yes, I am included in this) have a very hard time not over-packing. For some reason we have this idea that we “may” need those cute boots, or a few pairs of jeans, or seven pairs of heels. Honestly, you do not. A good rule of thumb, especially if you are a newbie to traveling – take what you set out to bring, and get rid of 2/3 of it. I KNOW! What the hell am I talking about? But, I am serious, you won’t need it, particularly on a tropical trip.

On a trip to the tropics, you definitely do not need to check a bag. One rolling carry-on, a nice big tote or handbag, and you are good to go. I promise. Here is what to wear, as well as what to bring to Hawaii.

Victoria's Secret Bikini Mix Match

A Few Bathing Suits

This is your new uniform while in Hawaii. They don’t take up much space in your suitcase, and if you buy a few different bikinis, you can mix and match the tops and bottoms. Three bathing suits now turn into nine separate combinations! If showing this much skin isn’t your thing, pack a couple tankinis, or perhaps a few one-pieces. I love that single-piece bathing suits are really in right now.  I currently am on the hunt for a really cute monokini.

My go-to choice for bathing suits: Victoria’s Secret (they win by far with their huge selection, varied prices, and selections based on body type)

The current bikini is only $30 and comes in 12 different colors for tops, and 24 different colors for bottoms.

Kenneth Cole Swim Tunic

A Swim Tunic

Swim tunics are both functional and stylish. Not only do they provide a great cover-up for your swimsuit, paired with a cute metallic flat sandal, they can pass for walking around downtown and also for grabbing a quick, casual bite to eat. Also you could pair it with a cute pair of cropped white leggings!

I like that the current tunic is a solid color without many embellishments. You can easily spruce it up and change the color scheme by adding some statement necklaces and bracelet bangles. I do love the tunics with beading as well, but I find simple pieces work best for transitioning them across multiple outfits. A perfect choice when you don’t want to pack too much.

Kenneth Cole REACTION Cover Up, Tunic Women’s Swimsuit. Comes in both white and black for $54 at Macy’s (yes, I know, a tiny bit over $50)

Madden Girl Embellished Sandal

A Couple Pairs of Sandals

A couple pairs of sandals will go a long way. Bring an embellished pair and a couple solid color flimsy flip flops (Old Navy is best for these, I love the metallic ones – gold and silver, they go on every vacation with me). These shoes don’t take up any space in a bag and with  flip flops, I can shove them in the side pockets of my bag, and you would never even know they were there.

Madden Girl, Creative Sandals Women’s Shoes Find these at Macy’s for $49

Victoria's Secret Jersey Dress Racerback

Jersey Knits

I ADORE jersey knits in hot weather. Hell, I adore jersey knits at any time. I am an extremely tactile person, so anything I wear, it has to feel good against my skin. Call me sensitive or call me picky, I know what I like. Jersey is the best knit to bring when traveling as it takes us so little space, and can easily be dressed up or down. Even Diane von Furstenberg agrees – read more about her packing tips here. A jersey knit maxi dress is perfect for a night out if you want to dress it up a bit.

This particular Victoria’s Secret dress I love. They always have a ton of jersey-knits available, in many different styles.

Pick this one up for $45 in either fuschia or olive here.

VS is always known for great sales and coupon/promo codes. If you need help finding one – shoot me an email!

Victoria's Secret Boyfriend Short

Denim Shorts

You know I love my denim. Although I don’t have experience with Victoria’s Secret’s denim line, I do love this style and am pining after a pair of Joe’s Jeans boyfriend shorts as we speak. But for the price, this is a steal. I love the boyfriend fit as it works with so many body styles, fits comfortably, and is casual-chic. I also love that they don’t show any butt-cheek. That is not cute. Also, they aren’t so tight around your leg you get that horrible fat-bulge where your shorts end. Yes – we can all get that, and it ain’t pretty.

For those that have tried their denim, leave a comment below and tell us what you thought of them!

So check these shorts out at VS – again, look for a sale, or ask me to help!

Tom Ford Whitney Black Sunglasses


Sunglasses are a must for any vacation. I have two pairs that I adore, two very different styles. Some days I am feeling a bit more glamorous, and go for the large framed Jackie O style, other days I am feeling my Ray Ban Aviators. No matter what your personal style is, it is important to bring a pair that you love, and that fits your face.

Online sample sale sites are the best way to find designer sunglasses at a fraction of the price. I am currently waiting for the next Tom Ford sale for the pair pictured to the left. (They are frequently available on these sites as well as Gucci, Guess, Marc Jacobs, Coach, etc.)

Some of the best sample sale sites for sunglasses: (click each for my invite code, as they are member’s only sites)

ideeli —   Beyond the Rack –  Row NineRueLaLa

Jessica Simpson Floppy Hat Collapsible

Collapsible Floppy Hat

A hat is a very important item to bring. It helps keep the sun off your beautiful face, saving you from those yucky wrinkles later on in life. Many hats are collapsible and can fit perfectly in luggage without taking up too much room. I think this one is adorable and comes in both black and tan!

Jessica Simpson Hat, Floppy Find it at Macy’s for only $39!!!

Also bring -

  • few feather-weight tanks and tees,
  • a cute tote (I would use the tote as one of my carry-on bags and then later use it to bring stuff to the pool/beach)
  • a clutch so that you don’t have to drag around a huge purse (perfect when you go out at night)
  • loads of sunscreen
  • self-tanner (read my post on the best picks for 2010)
  • a pair of tennis shoes (if hiking/walking for a long time, I like the Nike Free, they are super lightweight and compact down nicely)
  • a shawl or wrap (this is perfect for night time if it gets a little chilly and also a cute accessory for an outfit)
  • some cheap jewelry – statement necklaces, bangles,  chandelier earrings etc (don’t bring your expensive stuff, I’d hate to see it go missing!)
  • a pair of capris – whether denim, linen, or cotton – one pair is plenty

Remember, less is more when packing for a tropical trip! If you need to bring a pair of heels, that’s fine – choose a cute wedge for the tropics. Remember – it is a casual location, stiletto’s are just not the thing to wear. Enjoy your trip never forget to always travel in style! Update – Thanks to reader Natalie, she mentioned that there are some places in Hawaii where people love to dress up. With a jersey dress in a stand-out color, perhaps turquoise, hot pink, or an orange (I also love black), you can really find some ways to dress it up. If you must bring a pair of heels for that night out – only one pair of sexy shoes are needed. Find a pair that you can wear with multiple outfits! God, how great would it be if they could come up with collapsible heels!!! I better patent that, quickly!)

Love, K.

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{ 4 comments… read them below or add one }

Natalie April 17, 2010 at 5:31 pm

OMG! I’m so excited for you! I go to Hawaii once every year because my cousin lives there! One though that I noticed was that some people really really dress up there. Shopping is a dream come true there and the ladies who shop? They’re dressed to the nines! Me? I was the slob sitting on the beach with my pina colada…ahhhh….have a great trip!

Kirsten April 17, 2010 at 9:15 pm

Hey Natalie – This is a good point. Depending on what you are going for, an outfit to dress up in is very important. The jersey dress – perhaps in a standout color, turquoise, hot pink, maybe even black would be a great option. The key is to find something that will allow you to not take up too much space in your carry-on. Thankfully a cute little dress – those never take up too much space! And like I mentioned before, if you must, pack one set of heels, don’t go overboard! Thanks so much for the advice! Much love! xK

Australian Work Visa May 19, 2010 at 7:37 pm

One of the most important things to remember is that when you’re in Hawaii, you’ll be outside much of the time. So prepare for the sun, pack or wear comfortable foot-wear and clothes for walking, snorkeling, sailing and swimming.

Jos June 4, 2011 at 9:38 pm

Great website K…Very helpful!!

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