StyleBlazin’ In Montego Bay, Jamaica: What I Wore For A Bachelorette Trip

StyleBlazin’ In Montego Bay, Jamaica: What I Wore For A Bachelorette Trip

IMG_7652Photo: StyleBlazer courtesy of Jessica Wilkins

That awkward moment when you’re a week away from your beach vacation, but you completely abandoned your weight loss goals for it…yeah that happened. There I was all excited for my best friend’s bachelorette trip to Jamaica, and then looked at my waistline and thought, ‘oh yeah that’s what I forgot to do.’ I had one week to shop for a three day trip, one carry on bag, and unfriendly body measurements. This was my first time going out of the country, and I was determined to have fun despite my insecurities about my size. I wanted to be comfy, cute, and camouflage.

Since I was crunched for time, I got very methodical in the planning of my looks so that I would know exactly what to go for when shopping, lest I just wander around H&M aimlessly. We have all been there. One minute you’re in the front of the store, and the next you’re cradled in the fetal position in the corner of a fitting room, hoping that your friends didn’t leave you. Is that just me? Anyway. Our itinerary called for one excursion, three nights of partying, and swimsuits to chill on the beach during down time (there was no down time). I reached out to my colleague from Spirited Pursuit, because she travels the world in effortless style, and I wanted to get the tea on how to dress for a tropical vacation. We both concluded that I should go for looks that are casual, as Jamaica is not a very glammed up destination.

There’s something you should know about Montego Bay, Jamaica. First, it is hot. I mean hot. And humid. I know that it seems I’m stating the obvious, but it needs to be emphasized. So before I get into my full style breakdown, there are a few essentials you need to take with you to stay comfy and safe.


IMG_0195Photo: StyleBlazer courtesy of Jessica Wilkins

1) Water-Resistant Sunscreen – this saved our asses during our excursion. Don’t be the person who comes back from vacation red, inflamed, and peeling.
2) Waterproof Mascara – come hell or high water (there was literal high water) one should never be without mascara, especially if you’re forgoing your usual beat.
3) Bug Repellant Spray – the mosquitos there are like nothing I’ve ever seen. They were relentless.
4) Makeup Setting Spray – you obviously don’t have to be that girl and have a full beat in the pool, or in the ocean. This is not Love and Hip Hop for crying out loud, but when the night gets cooler and you want to get glammed up, you need to secure your makeup with a bomb ass setting spray.


IMG_7699Photo: StyleBlazer courtesy of Jessica Wilkins

Now that, that’s out of the way, click through for style diary during my three day trip to Montego Bay, Jamaica.

Day One

For my 5 AM flight I wanted to be very cozy, and if athliesure brands have taught us nothing it’s that you don’t have to sacrifice cute to be comfy. I did some layering so that I could go from the cool early morning temp in New York to the warm, tropical climate in Jamaica without freezing or burning up.

Screen Shot 2016-06-26 at 10.11.25 PMPhoto: Topshop River Island Foot Locker Stella McCartney Ray-Ban

IMG_7758Photo: StyleBlazer courtesy of Jessica Wilkins

As soon as we touched down, it was off to the resort pool. Let’s take a moment to be thankful for the resurgence of the one piece. I realized that I brought New York with me with all of the black I was wearing to the pool, so I added a pop of color via my favorite red lip combination: MAC Ruby Woo and MAC Lady Danger.

Screen Shot 2016-06-26 at 10.20.21 PMPhoto: Net-A-Porter H&M M.A.C

IMG_7760Photo: StyleBlazer courtesy of Jessica Wilkins

For our pre-game dinner, the maid of honor requested we wear all black (I just couldn’t escape it). I made a point to bring minimal accessories that would go with every look I packed. This way I didn’t overpack, or overdue it. We followed the advice of the locals and ventured off the resort to a really amazing outdoor club; hence, I brought a change of shoes. Word of advice: go off the resort.  You will not experience the fullness of another culture without venturing off a little (as long as it’s safe).  It was such an amazing experience to be in a space where everyone looks like you, everyone is getting along and warm, and welcoming.  There were guys who came up to us to make sure we were okay, and we even ran into some of the resort staff who made sure we made it back safely.

Screen Shot 2016-06-26 at 10.39.25 PMPhoto: Wolford Steve Madden Barneys New York 6PM Harvey Nichols

Day Two

In spite of our late night partying, we were up bright and early to catch our catamaran to go snorkeling and climb the famous Dunn’s River Falls. This was our only excursion, so I wanted to be sporty and appropriate for the day. I needed to be able to slip in and out my cover up, so I opted for a sporty one piece swimsuit, cut off denim shorts, and the obligatory swim shoes (not pictured) for the climb. I also brought a huge scarf which I tied into a turban to make sure my hair was okay for the pics. I will not be caught slipping as the only girl with no weave and pixie cut.  I recommend having easy hair for a tropical trip. No one should be super concerned about their edges while experiencing nature.  Hats and turbans are your friend.

Screen Shot 2016-06-26 at 10.59.27 PMPhoto: Shop Bazaar One Teaspoon STYLEBOP H&M Nike

Day Three

Our last night was pretty chill since the bride to be was exhausted. We actually ended up kidnapping her from her room to make sure she lived it up on the last night. There was a party on the resort, and let me tell you Jamaican people know how to party. I opted for a cool maxi dress, and I cinched the waist with a belt that I’ve had for years. While I love the whole flowy boho look, it doesn’t translate well when you’re well endowed in the front and the back. In your mind you look like Lisa Bonet, but you actually just look pregnant. Hence, I cinch my waist whenever possible. BCGBG is one of my favorite brands for cool belts.

Capture 2Photo: H&M Zara Aldo BCBG

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