The Fashion Sessions

Travel

Vacation Looks - What I Wore in Hawaii

April 10, 2020
Updated May 9, 2023

My first trip to Hawaii was absolutely magical!  From the gorgeous scenery to the amazing activities and seriously good food, Maui did not disappoint!  I planned way ahead for what vacation looks I wanted to take with me.  I wanted to be comfortable but also wanted to look like a seasoned islander.  Here’s a look at what I wore in Hawaii.

Maxi dresses are perfect for so many occasions, but they are especially fitting for a beach vacation.  Here are some of my faves from our trip!

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The Experience

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I ended up taking quite a few swimsuits and cover ups with me, and I am so glad I did!  I think it’s important to have a variety of swimsuits.  What you want to hang by the pool may be different than a suit you need for fun activities like hiking to waterfalls and ziplining.  Also, I didn’t want to wear a suit again after I had worn it to the beach because sand likes to stay with you!  The good thing is that swimsuits and coverups don’t take up a lot of room in your suitcase.  So I say the more, the better!  Here’s a look at what I took.

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Highlights

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You’ll need several different looks for exploring your resort as well as for all of the activities to do in Maui.  And there are plenty, trust me!  The Road to Hana, ziplining, casual walks to order another incredible açaí bowl…each day is an adventure.  Here is what I chose for some fun, casual outfits.

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Tracy's Recommendations

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Maui was my favorite vacation ever, and I truly look forward to going back to the Marriott Wailea Beach Resort!  Everywhere you go looks like a postcard, so you’ll fit in no matter what you pack.  I hope I’ve given you a little inspiration on what to pack for your tropical getaway.  Just have fun, be comfortable, and don’t forget to say “mahalo” to everyone you meet!

Tracy Cartwright

Tracy Cartwright

Tracy is a fashion and lifestyle blogger helping women feel confident through personal style. A former CPA turned full-time content creator, she has been styling and inspiring women for over 5 years at The Fashion Sessions.

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