Airport style

Complete Suitcase: What To Wear To Puerto Rico For Men & Women

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The best part about vacation is enjoying a different location and environment. So Rob and I thought we would showcase what to wear to Puerto Rico for our daily activities. We may have been on “island life” but I have to admit, that it’s fun to wear some fancy things on vacation.

Quote of the day: “If you never question things, your life ends up being limited by other people’s imaginations. Take the time to think and dream, to question and reconsider. It is better to be limited by what you can dream for yourself than by where you fit in someone else’s dream.” James Clear

This quote is perfect for our vacation suitcase post about what to wear to Puerto Rico. Because if you only think you will pack casually for your tropical vacation, then you might be limited about where you feel comfortable going when you’re there.

I know most people concentrate on packing the very least they can get away with and then trying to make sure to wear everything they took. But I came to realize that it’s a silly game to play. Who cares if you take extra items and don’t wear them? There is no prize for packing.
So make your life easier and include some extra things for your next vacation.

This vacation is thanks to SheBanks. I won the trip (both the resort stay at Villa Montana and the flight) by sharing about this new app which is a financial planning app for women that will help you reduce debt, increase savings, and provide an analysis of your monthly income and spending.

You should definitely sign up for the emails below. Besides the free eBook, my email family gets personal tidbits of what’s going on in my life along with other happenings, sales, information, giveaways, extra photos, and interesting articles.

Airport Outfit

Airport style for travel
Skirt: Just Be Youtiful~~Jacket: Naomi & Ruth~~Sneakers: Converse-thrifted

Wearing a skirt or dress is my favorite airplane kind of outfit. It makes the bathroom stops much easier (no puddling of material on the floor) and as long as I choose a flowy one, they are easy to sit in. I wrote about my other essentials for my airplane outfit in the past.
This skirt is so versatile because it can be worn as a dress too, so I figured if I needed another outfit, I was covered.

Insider tip: I basically wear the same thing on the departure and return trips. I change out my shirt that is next to my body (and my undies), but otherwise, it makes it easy to plan.

The hard part of travel is going from warm to cold temperatures (or vice versa). I wore my compression socks and figured I would take them off when we arrived in Puerto Rico. I couldn’t wear my comfy sandals because Phoenix was too cold (and the airports are too). So I grabbed these thrifted Converse sneakers.

The other layers included this SheBanks t-shirt (seen in my travel video), jacket, and scarf which could all be removed if it was too hot when we landed in PR because there was a tank top under it all.

What to Wear to Puerto Rico at the Beach or Pool

It’s only in the last couple of years that I have embraced two-piece swimsuits. One of the reasons they tickle my fancy is the option to mix and match. And now that we live in a state where we go to the pool much more, it’s nice to have a variety.

I have worn this swim bra under a crochet top on the blog last summer. One of my friends on Instagram touted it as a wonderful option for a strapless bra. I didn’t find that it stayed up enough for my preference (she has a smaller chest than I do), but I wear it often for water aerobics.

This mid-rise swim bottom is my favorite. You’ll see the higher-rise variety below, but because I’m a tad short-waisted and the girls hang low, then you don’t have as much real estate between the two pieces.

For my cover-up, I used this kimono that I could tie in different ways. The other essential was my hat.

Insider tip: Most beaches tend to be windy, so it’s good to have a tight-fitting hat or one with ties. If your hat doesn’t have ties, you can DIY that detail as I’ve shown here.

This swimsuit is also a mix-and-match. I bought the bottoms from Target (we showcased our Target swimwear last spring). My suit from Target came with a different bra top (the same color).
BTW, I do tuck the swim trunks down about an inch to the inside so they don’t take up so much real estate on my trunk.

But for this trip, I wore this push-up bra top from Goodwill.

Funny story: When I found this bra top, I asked my mom if it would be hard to take out all of the paddings. I’d never had a push-up bra before and didn’t think I needed it. (I’m a size 30D). Once I got home and tried it on, I was gaga. I love how it pushed up the girls. It’s not super obvious in the photos but in real life? Oh la la!!
So at age 56, I became a push-up bra lover, LOL!!
Moral of the story: Never say never.

This purple set is from Aquashape Dolfin swimwear. I also have solid purple bottoms that I mix and match.

I used this white cotton maxi (from Naomi & Ruth last season) as my coverup.
And yes, I do wear earrings since we weren’t actually going INTO the ocean.

Rob’s swimwear included his ice cream trunks and lobster ones. We were both trying to be respectful with sun protection, so he kept his t-shirt on every day.

Daytime Outfits

Colorful style for women and what to wear to Puerto Rico
Top: Willow Tree Boutique~~Shorts: J. Crew-thrifted~~Sandals: Walking Cradles “Nella

I saw this top on my friend’s feed on Instagram and couldn’t resist. I didn’t think I would bring it with me, but I’m so glad I did. It’s shaped more like a kimono-very loose and the sleeves are slits, not sleeves. It’s from a small boutique called Willow Tree and is under $50.
I wore my “Nella” sandals from Walking Cradles. There is a ton of information in this article about this sandal construction that makes them ideal for everyday wear. And these sandals come in 4 different colors.

Second Day

Maxi dress and kimono
Dress: Naomi & Ruth~~Kimono: Top it Off~~Sandals: Open Edit-Nordstrom

I wore my white maxi dress with the kimono over it to walk the beach. I would give this outfit a thumbs up because I was wonderfully covered from the sun. Sure, I had sunscreen on my arms, chest, and everywhere, but it was nice to have my legs covered with the dress. When the waves came up, I just lifted the dress. Sure, it got wet a couple of times, but hey, that’s beach life.
The shoes were purchased last year, but I took them off to walk the beach. But it was nice to have them when walking on the sidewalk back to our room.

Third Day

Outfit for exploring as what to wear to Puerto Rico

This was the outfit for going into the town of Isabela. I figured we would be walking around the square and might not have much shade. The green top is a sun shirt that I found while thrifting last summer.

I wore a knit skirt that is also thrifted and my sneakers. These Converse sneakers don’t have much support so I included my custom-made orthotics from ages ago.

When packing, I made sure my purse strap could be lengthened to be a crossbody so I could be hands-free. I even used the strap clip to hold my hat.

The earrings are from Wild Cloud. It’s sustainable jewelry that gives back.

Insider tip: Shirts with UPF in them are so practical for beach vacations. You can throw them over your swimsuit at the beach or wear them as part of your everyday outfit.

Dinner Time Looks

Two piece dress for what to wear to Puerto Rico for women

I found this top at Banana Republic when we went shopping for my birthday in December. I wasn’t looking for summer things, but this was a crazy deal (like $6 I think. I shared my birthday haul here on Facebook which is where you’ll see the blue dress below too).

Then when I was on BR’s site, I saw this matching skirt and figured I should get it. Because I used my rewards, it was less than $1.

I accessorized with turquoise items and wore a pair of Walking Cradles sandals called Naomi. This style comes in 3 different colors. It’s the same construction as my gold Nella sandals and is super comfortable.

Here’s the other dress I found for a deal at BR last month. Of course, I took a denim jacket for the cooler evenings and carried my yellow purse with the strap shortened.
Again I wore the Naomi sandals but I could have easily worn my Nella ones too.

Insider tip: The dress had the opportunity to create a Marilyn Monroe moment, therefore, I wore bike shorts under it. Another good reason to try outfits on before you pack is that I wouldn’t have remembered this otherwise.

I won this dress (and check out all the ways it can be worn in this Tiktok video) 2 years ago and always thought it would be the perfect resort dress. This evening we went to a fancy restaurant off the resort. A fancy restaurant called for heels so I wore these Porsha sandals from Walking Cradles (modeled here). Don’t let the heel height of these sandals make you think they aren’t comfy. I could walk for ages in these.

I did include this yellow poncho for the evening chill. And the shoulder-scraping earrings were made by my friend, Judy.

Men’s Fashion of What to Wear to Puerto Rico

It wouldn’t be fair not to include Rob’s outfits for what to wear to Puerto Rico. Men can look as wonderful as women, and Rob’s fashion has evolved so much over the years. I always love it when my mom calls him dapper because that wasn’t how he used to dress when I first met him.
Yet having a good style and being open to new fashion can be a boost for our confidence. It sure has been for my husband.


Staying stylish for men with what to wear to Puerto Rico

For the day that we went into Isabela, Rob wore his green pants, sneakers, and his man purse. Maybe the man purse is called something else, but that’s what we call it.

Rob’s favorite way of dressing is to wear a t-shirt and layer a button-up shirt over it. He re-wears the button-up shirt many times before throwing it in the wash. And it’s a wonderful way to use his print mixing skills.

What to Wear to Puerto Rico in the Evenings

One of the things we read about Puerto Rico is that only men tourists wear shorts, especially to nice places. So Rob made sure to include lightweight pants in his suitcase.

Mens' style what to wear to Puerto Rico for evening.

Rob had been looking for some other pair of linen pants and I found these at Clothes Mentor. Would you realize that they are women’s pants? Of course not!! They have an elastic waistband so would work for men or women. And they fit him perfectly-no alterations needed.

I always love how bold Rob is with his print mixing. He will tell you that he follows this cute blogger who has opened his style options (that’s me!!)

Guys and what to wear to Puerto Rico

I think this is one of my favorite looks as part of what to wear in Puerto Rico. Even our Uber driver (who we got to know well said Rob looked like a local. Thanks, Paradise Transportation.

These shoes are a fabulous option and the best part is they say “LOVE” on the side in the straw.

Colorful style for what to wear to Puerto Rico

Rob re-wore the green pants from our day into Isabela and changed out his shirts. Wearing the straw shoes make it a tad fancier than the sneakers.

Insider tip: Cuffing the pants gives off a tropical vibe.

Thank you

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My Goal

Thank you for visiting my space on the internet. I like to showcase how it’s never too late to look great for women of any age, size, or working with any kind of budget.
I feel I’m here to help move beyond the fashion rules of yesterday and evolve. Style and clothes are made to give you joy. Not cause us stress because we are worried about what others think.

My hope is that you get ideas and inspiration from Charlotte, Lesley, and myself. It’s not about copying what we wear, but about using what you already have and updating items along the way.
Most of all it’s getting us to think differently and dare I say, have fun.


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