My Braless Vacation Went Pretty Much as Planned
I think I’m starting to get the hang of this

When we touched down in Jamaica a few weeks ago, the humidity hit like a freight train (a freight train carrying tanks of water). Right then and there I made up my mind to go ahead with my idea of going braless all week. It was just too dang hot and sticky to do anything else.
The resort we stayed at was relatively small and everything is open-air, except for your actual bungalow, where air conditioning is available. Everything from check-in to dining takes place in open-air spaces, and although the breeze made the heat manageable, most days it was very humid. We had a couple of good thunderstorms at night that helped to clear out some of the humidity, but even so, I would have been really uncomfortable in a bra, and who wants to be uncomfortable on vacation?
I’d flown in a very unstructured bralette just to have a little support for schlepping through the airport, but the very first thing I did when we got into our room was to take that thing off and put it away. I changed out my traveling clothes for a long t-shirt dress and instantly felt better. I’d brought along some stick-on nylon nipple covers, but James convinced me to take them off because he could see them through the fabric.
“You look like you have the world’s biggest areolas,” he quipped. “and it looks weird. Go natural — you’ll look like a woman.”
He had me convinced. I was comfortable and hungry, and in no mood to care what other people thought if my nipples were showing a bit, so we headed over to one of the open-air restaurants and got a table. The breeze from the ocean was nice, but I was still glad to have something on that wasn’t very restrictive. Unless I’m doing something more active, I don’t really need a bra and it was definitely nice and much more comfortable not to have to bother.
The next morning while we were getting dressed for breakfast, I saw a woman walk by in a thong bikini. “Well,” I thought to myself, “I guess that’s one more sign that I don’t need to be so uptight.” Sure enough, over the course of the next several days, I saw several women in thongs or near thongs and it helped me to further relax into just being comfortable. I tossed on a cotton t-shirt and some shorts and headed for the restaurant. Nobody seemed to notice or to care if they did that my nipples were visible through the fabric.
One day we went horse-back riding on the beach, and I did put my bralette back on because I wanted to wear a long-sleeved white t-shirt for sun coverage, and I didn’t want to end up looking like I was in a wet t-shirt contest when we went into the water. It turned out that only my capri pants got wet riding in the ocean, but again, the support of the bralette was good for the jolting momentum of being on a horse.
Riding a horse in and along the ocean was amazing, and I’m so glad that I got to do it. I bought a loose sundress from a local vendor after we got done, and it was nice to have yet one more comfortable piece of clothing that looked nice but that I could reasonably wear sans brassiere. I’ve worn it several times that way since we’ve been back at home.
What this braless week taught me is to be less self-conscious. It’s definitely easier to push the boundaries when you aren’t in your regular environment. What happens in Las Vegas, right…? But it also helped me to just get more comfortable with a silhouette that was more natural looking — something that I’ve been working on for the past couple of years.
I still wear a bra back at home at least some of the time, but a very light unpadded one and I no longer worry if my nipples show. That right there is a huge win because it’s something that has driven my bra and clothing choices since puberty. No more — and if it’s really hot, forget it — I am not putting one on. Bras and really hot, sticky weather just do not go together.
I’m still working on confronting many of my internalized stories from society about what is “appropriate” for even casual situations, but I definitely feel like my week at a hot, humid, Jamaican beach went a long way toward assisting with that. Human bodies are not inherently sexual, and female nipples are not obscene. Plus, my body belongs to me, and what I choose to do with it is really nobody else’s business. After decades of messaging that my body somehow belonged to others, it’s been a journey to reclaim it for myself.
I’m not 100% there but I’m much further along than I used to be. One Love, Jamaica — thanks for your help!
© Copyright Elle Beau 2023
