What to Wear in Boca Grande, Florida

4/9/2020

If you're heading to Boca Grande, Florida's most exclusive enclave, check out these preppy essentials you'll want to have in your suitcase when you cross the bridge to Gasparilla Island.

Disclosure: some of the links below are affiliate links. If you purchase a linked item, I will make a commission, at no extra charge to you. As an Amazon Associate, I earn from qualifying purchases. Post updated, April, 2020.

What Should I Wear to Boca Grande?

So you're planning a trip to Boca Grande! Lucky you!
"Boca" is a phenomenal little spot - a quiet corner of Florida that time has left behind. Feel free to let your preppiest and most pastel outfits out of the closet for this adventure to Gasparilla Island!

Boca Grande, Florida

You can even pick up the essentials once you arrive, as Boca features some lovely, high-end shopping options, such as Lilly Pulitzer and J. McLaughlin.

Whether you're staying at The Gasparilla Inn & Club, or just popping over from the mainland to explore Boca Grande for the day, Boca doesn't disappoint. Don't forget to keep an eye out for famous faces (so that you can quickly give them space and pretend you didn't see them!) and grab a drink at the Loose Caboose, once you're there. For more on the best restaurants in Boca Grande, check out the full post.

Let's talk packing essentials for your trip to Boca Grande!

For the top things to do during a visit to Boca Grande, check out the full post!

What to Wear in Boca Grande:
Sun Hat

I have the most phenomenal, monogramed straw hat from Kailey's Monogram Boutique on Etsy. I really can't recommend my hat from Kailey's highly enough - it even survives being packed in suitcases repeatedly.

Amazon also has some cute, pre-made (non-monogramed options).

That Florida sun gets toasty, even in the winter months!

Perfect for the beach, or for walking around and protecting your sunburn for yesterday, a floppy sun hat is really a must.

Boca Grande Lighthouse, Boca Grande, Florida

What to Wear in Boca Grande:
Novelty Earrings

A bit of whimsy goes a long way on stylish Boca Grande. It's amazing how many adorable statement earrings I keep finding - and my collection just keeps growing! Earrings are a fun way to keep things whimsical, without adding extra layers in the Florida heat!

Sporting my new coral dress, purchased in Boca Grande!

How adorable are these pineapples?

And while you're here, be sure to check out my other posts about what to do and where to eat in Boca Grande!

What to Wear in Boca Grande:
Bathing Suit & Cover-Up

Invest in a comfy bathing suit for your time in Boca Grande, as you'll be spending a fair amount of time in it! Gasparilla Island is home to several *gorgeous* beaches, and many residences, communities also boast their own pools. Depending on the time of year, one of my favorite shops in the world, Tuckernuck, generally has some unique, and super preppy, selections, as well!

Of course, you'll want to include a cover-up-and don't miss an opportunity for style there as well, as cover-ups are prime island style! I've actually found some good ones on Amazon, and you can even buy them in the nice shop at the Gasparilla Inn, if you aren't able to find one in advance, or in the tons of lovely, high-end shops on the Island!

Private beach for Gasparilla Inn Guests on Boca Grande

What to Wear in Boca Grande:
Bright, Floral Dresses

I went to college in Virginia, and thank goodness I kept all the dresses from those steamy summers (though, let's be honest, it's hot in Williamsburg through the end of October).

With the heat in Boca Grande, one of our most recent visit was in late April, dresses are my usual go-to, just to try to keep things relatively cool! I especially like dresses for dinners, as they'll suit any dress code. Dress code, you ask? Yes, you'll want to be sure to confirm dress codes at the higher-end restaurants on Boca Grande. For more on that, check out Where to Eat on Boca Grande.

Of course, you can't go wrong with Lilly!

Rocking Lilly on the beach!

What to Wear in Boca Grande:
Preppy shorts

It gets hot, hot, hot in Boca Grande, so you will definitely want to include several pairs of shorts in your suitcase. I'm all about white shorts with the scalloped bottoms, as they go with literally anything else you've packed for this brightly-colored trip!

Luckily, J McLaughlin, which has a store on Boca Grande, also has the most phenomenal shorts. Personally, I prefer the longer versions, but maybe that's just me getting old!

What to Wear in Boca Grande:
Straw purse

This is the definitely the year of the straw purse and it's no exception in Boca Grande! I have found some super cute (and affordable) options from TJ Maxx/Marshalls. And, of course, there's trusty Amazon!

What to Wear in Boca Grande:
Bright blouses

For popping around the shops, grabbing a drink, or lounging by your pool, you'll want to load up on comfy, brightly colored tunics, such as this Helen Jon shirt dress. I also recently found Cabana Life, which has a ton of sun protective tunics!

What to Wear in Boca Grande:
The right shoes

You'll want to bring a few different types of shoes, for beach, strolling around town, pool, and, of course some options for dinner both at home and out in town!

I always include the options below, at least! Jack Rogers (flip slops and heels), and some top siders for boating. If you're visiting in winter, don't forget some more traditional loafers, as well!

What to Wear in Boca Grande in Winter

I've gotten a few questions about what to wear in Boca Grande in winter, so I've added this new section into this post! I have it on good authority that the "go to" outfit in Boca this past winter was white jeans and a light, cashmere sweater/tunic, such as the Catalina Sweater from Mer-Sea & Co. Dudley Stephens, a newer "preppy staple," should also be included in your suitcase!

What to Wear in Boca Grande: Brands

If you're looking for browse a bit, here are my recommendations of the top brands you'll want to check out before your trip!

Thanks for stopping by!

And while you're here, be sure to check out my other posts about our visits to Boca Grande!

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