Planning For A Caribbean Trip With From The Heels Up

Hi everyone!

This is fashion blogger, Amanda Korina from FromTheHeelsUp. I recently traveled to Montego Bay, Jamaica and had the time of my life – in style of course. I absolutely love traveling mostly because the fashion and culture is different everywhere I go. I can get into a specific character based on the destination sort of like role-playing. Planning my looks for trips is so much fun! I get asked all the time how do I pack? How do I plan? Where do I shop? So I’m going to share my personal tips and advice on packing for your next Caribbean destination. Also, outfit details of course!


Swimsuit: The Naked Tiger
Sunglasses: Desi x Quay Australia “High Key”

Jumpsuit: Solid and striped via Net-a-porter
Shoes: See By Chloe via MatchesFashion
Bracelet: Banana Republic
Ring: H&M
Sunglasses: Tom Ford

Swimsuit: Urban Outfitters
Shirt: ASOS
Ankle bracelet: Express
Sunglasses: Desi x Quay Australia “High Key”


Top: Shop Planet Blue
Shorts: Romwe
Earrings: H&M
Sunglasses: Chloé



Swimsuit: Plush Swimwear (site no longer exists)
Cover-up: Venus
Hat: Lack of color


Dress: Pixie Market
Shoes: See by Chloe via Matches Fashion
Hat: Lack of Color
Bag: Zara

Pajama: Victoria’s Secret

Top: SheIn
Shorts: H&M
Choker: Express
Sunglasses: Tom Ford


Everywhere I travel to I stick with a theme or should I say a “vibe” – which is almost always connected to where I am going. For Jamaica, I packed fringed pieces, tribal prints, straw hats/bags, vibrant colors, accessories with tassels and shells, and off-the-shoulder tops. Sticking with a theme keeps me focused when i’m vacation shopping.


I plan every outfit before-hand. This avoids over-packing and that annoying feeling of not knowing what to wear once i’m at my destination. I try my best to incorporate a variety of looks: dresses, shorts, maxi skirts, etc. Vacation is the best place to be fun with your clothes!


Swimsuits are the most important part of your trip. I mean, you are in a swimsuit more than you are in real clothes so why not step out of your comfort zone and have fun with prints and cut-outs. Two-pieces are cool but one-pieces can be sexy as well! Don’t be scared to wear one. My advice is pack extra itty bitty two-pieces to change into after wearing a one-piece. Snap that photo and get your tan on. That will avoid crazy tan lines!


I am the biggest fan of cover-ups. In my opinion, it makes the swimsuit. After all, you don’t want to go into bars and restaurants half-naked. There are so many options: skirts, shorts, kimonos, button-downs. Have fun with it.


Pack versatile pieces. No need to pack tons of accessories! I pack three bags: a beach bag, a day-time bag (big enough to hold my cameras and essentials) and a clutch for going out at night. I try my best to pack classic and timeless bags and shoes – again, to avoid over-packing.


90% of the time – dresses, rompers, and jumpsuits are my go-to on an island. It’s easy, lightweight, and simple. Don’t over-do it, comfy and chic is the goal.

Hopefully you found this post super helpful and you’re inspired for your next Caribbean vacay!


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