What To Wear in the Cayman Islands

When it comes to style, the Caribbean is an eclectic blend of luxury, casual beach vibes, and local island flavor. With all these seemingly contradictory tastes, it can be hard to know what to wear in the Cayman Islands. By no means am I well-versed in the world of fashion. However, I have identified eleven island girl essentials that have become staples in my Cayman wardrobe. I believe these could be welcome additions to your Caribbean closet as well. Whether you are preparing for a move, planning a visit, or are already living in this tropical paradise, I hope this essential list infuses your life and your attire with practical yet stylish island vibes.

# 1 Linen Pants

Effortlessly elegant, linen pants are a Caribbean wardrobe essential. I found the below featured pair at the Humane Society Thrift Shop (a recurring theme when it comes to my island attire). They are light, comfortable, and seem to pair with everything. Whether you’re chilling on the beach or adventuring around the island, these linen basics are a must have when you’re planning what to wear in the Cayman Islands!


# 2 Shades

Here in the Caribbean, we would be nothing without our sunglasses. Their practicality combined with serious style factor make them an invaluable accessory for island life. It is no secret that they can also be a great prop for a shameless brunch flex as well as the standard selfie. My featured shades were purchased in Camana Bay at De Sunglass Man.


# 3 Collective Swim Suits

When I was living in the Midwest, I literally purchased ONE swimsuit a year to wear throughout the few fleeting summer months. Here in Cayman, it is a very different story. There seem to exist infinite opportunities to parade around in swimwear. Even my frugal self has numerous rotations of one pieces, tops, and bottoms. My go-to bikini is Collective Swim’s black Kittiwake (named after the Grand Cayman shipwreck). Designed in and inspired by the Cayman Islands, I would recommend Collective Swim to any local or visitor looking for something uniquely Cayman and readily available on island.


# 4 Wide Brim Beach Hats

We love beach hats for the same reasons we love sunglasses — they are practical and timelessly chic. Something you probably did not know is that in a pinch, they make great shopping baskets! Warning: the cashiers may laugh at you but just tell them that you were inspired by Island Diaries. They’ll think it’s a movement…and that’s what it is 😉


# 5 Boyfriend / Button-Down Shirts

Prior to moving to Cayman, I would have never imagined that button downs and oversized boyfriend shirts would become such key players in my wardrobe. Coming from MinneSNOWta, I was dreaming of minimal-coverage island attire. I wanted the kind of tan I could never achieve in the Midwest. Months after moving, I find myself covering my arms every chance I get! Partly in an effort to block the sun but also because my body has acclimatized, no longer sweating profusely the minute I leave the AC. Boyfriend shirts and button ups are great for sun protection and provide a laid-back, beachy feel for any occasion. The Humane Society Thrift Store has quite the abundance of these styles. That is where I found the below featured tops!


# 6 Colorful, Statement Jewelry

The Caribbean invites a certain boldness in color and style than just wouldn’t make sense in other parts of the world. Since living in Cayman, I have unearthed the most unique, fun earrings (from the thrift store) that have become conversation pieces at every dinner or event I wear them to. Don’t go searching for this kind of jewelry though…it is best to let it find YOU.


# 7 The Iconic Kirk Grocery Bag

What costs $1 and serves as the perfect beach companion? Why, a reusable Kirk Market bag of course! While not the most luxurious of accessories, it gets the job done and adds local flavor to your island wardrobe.


# 8 Ultra-Versatile Denim Skirts

Leave it to the American to call the denim skirt an “island essential.” Say what you want, it truly goes with everything and is great to throw on over swimsuit bottoms. And yes indeed, both the below featured skirts are from the Humane Society Thrift Store.


# 9 The Romper

Back home I swear I considered buying a romper once every couple of months and they never made it past the dressing room. Living in the Caribbean, rompers have a certain je ne sais quoi that just works for the island lifestyle. Light and airy, this style offers a beachy, boho vibe that can be dressed up for a brunch or left casual for a beach day. Check out more of my thrift store finds below!


# 10 Head Scarf / Bandana

Beach-waves are a highly-coveted hairstyle that are quite achievable when living by the ocean. As lovely as this style is, it can lead to some pretty unruly hair. Not to worry, I have the perfect fix for this. Head scarves and bandanas are a simple and chic way to keep your hair out of your face and appear effortlessly beautiful wherever your island adventures may take you!


# 11 Comfy Slip-Ons


If my students didn’t ask me to tie their shoes on a daily basis, I may have forgotten how to do it by now. That is how infrequently I lace up because practically all of my shoes here are slip-ons. Flip-flops are an obvious essential if you are beaching on the regular; however, I would also recommend investing in comfortable sandals that can come on and off at a moments notice. This style is perfect for impromptu beach walks, beach restaurants, boat parties, and every occasion in between. Featured below are Viscata Menorcan sandals and an island-found pair from No. 1 Shoe Shop. Ideal shoes to wear in in the Cayman Islands!

Fun, beachy, and practical — those are the three words that describe my island wardrobe and I don’t see myself deviating far from this style anytime soon. The 11 island essentials I described today add comfort and lightness to the Caribbean lifestyle. Next time you are wondering what to wear in the Cayman Islands, take a page from Island Diaries and be sure to consult your local second hand stores! Happy shopping!

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