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When I hear Hawaii, I think skimpy bikinis, short shorts, and sun-scorched skin—it feels quintessentially summer. That all changed when I went on a recent trip right at the onset of fall; it was the absolute perfect, middle-ground weather. It was sunny, but I wasn’t sweaty.
I wasn’t prancing around in a two-piece all week, but I was able to wear shorts and minidresses and feel totally comfortable. Honestly, I can’t think of a better time to venture to the Aloha State.
Romer House Waikiki.
I stayed at Romer House Waikiki, a boutique hotel and intimate oasis just minutes from the ocean. The newly renovated, mid-century hotspot offers numerous built-in activities on the property, so I wanted to have a fitting ensemble for each occasion. From the built-in lounge to poolside sound baths and traditional Hawaiian luaus, I knew I had to diversify my looks. I was also part of a large group, so my outfits had to stand out.
While fall weather in Hawaii is mild, it still requires a more strategic wardrobe lineup. Scroll through below to check out everything I packed for my autumnal Hawaiian vacation.
Bleusalt The Perfect T Dress
Down From $200
This past year, I really aimed to elevate my airport game. When you feel stylish in-flight, it sets the tone for your trip. I recently discovered the Meghan Markle-approved brand Bleusalt, which totally lives up to the hype. The brand’s tencel modal fabric is the most comfortable fabric I’ve ever worn. The Perfect T Dress was indeed perfect, because comfort aside, it’s also designed with four percent Spandex for a custom fit, and it’s the perfect length to feel stylish and covered all at the same time. When I’m not traveling, I can easily step out in this to run errands or go on a neighborhood stroll with sneakers.
This set speaks to the lively, colorful nature of the tropical locale, but with a length that caters to cooler temps. Heading to the hotel’s tropical disco especially, I knew I wanted this paisley design to help me stand out. Dancing through the night at The Lei Stand Waikiki, I felt comfy and chic in the 100 percent cotton two-piece set.
Equal parts chic and comfy? Sign me up. These breathable, podiatrist-designed heels can be dressed up or down. It added a little oomph to my shorts and button-down duo for lunch at the hotel’s 855-ALOHA restaurant, while giving myself the ability to walk endlessly, pairing these with a long dress. They’re adjustable and fun, getting the job done.
Andie Blue Multi Abstract Floral Mock Neck Mini Dress
Another key colorful fall ensemble, this beauty stole the show when we set sail on the ocean just steps from our hotel. Even as it got chilly, I felt covered enough in this gauzy woven chiffon piece. While we hopped on the boat for a late afternoon adventure, this loose-fitting balloon-sleeve mini easily segued into night as we skipped merrily through the sand and off to our dinner destination.
Karen Millen Floral Printed Mesh Ruched Long Sleeve Maxi Dress
For our final night out on the town, I wanted to make a Hawaii splash. And that I did! Imagine a dress that truly hugs you in all the right places—this was it. I’ve got curves, and it’s easy to get frustrated when certain pieces don’t fit me the way they fit my friends. This bad boy was made for me. Thanks to a blend of polyester and elastane, I strutted through Honolulu with a sculpted waist and a colorful, show-stopping ensemble.
Parting is such sweet sorrow, and bidding adieu to the best trip of 2025 was no easy feat—but at least I got to slip away in style. Much like my arrival ‘fit, my departure had me clad in another chic black number. Designed with travel in mind, this sleek pick from Spanx had me slithering into my economy-class seat, thanks to tencel modal and breathable, four-way stretch fabric. And the cinched waist? The perfect added element of style and fit.
