What to Wear to Gasparilla?

Ah, the eve of my hometown’s biggest holiday… Gasparilla!

From Wikipedia:

The Gasparilla Pirate Festival is an annual celebration held in the city of Tampa, Florida. Held each year in late January and hosted by Ye Mystic Krewe of Gasparilla and the City of Tampa, it celebrates the apocryphal legend of José Gaspar (Gasparilla), supposedly a Spanish pirate captain who operated in Southwest Florida.

The theme is an “invasion” by Gasparilla and his men, which begins when the “Krewe” (made up of residents of the city) arrives on a 165′ long pirate ship, the Jose Gaspar, in Tampa Bay and land near downtown Tampa.

The mayor of Tampa then lends the key of the city to the pirate captain and a parade ensues down Bayshore Boulevard, one of Tampa’s major streets. The krewes throw beads, coins and other items while shooting blank pistols from floats during the parade. The average attendance for the event is over 400,000 people.

The age old question is, “What do I wear to Gasparilla?”

GASPARILLA

Allie Style:

Shoes: However cute you think those 3 inch pirate boots are… You’re going to be hiking all over town, probably walking 5 to 7 miles, at least. Oh & you’ll be wasted. Just say NO & grab something conformable. Also, yes, we live in Florida, it’s 75 degrees… but rethink the sandals. There are HUGE crowds & you’re feet will get stepped on, beer will spill, you may step in dog doo, no sandals.

Pants: Feel free to wear shorts, skirts, jeans, whatever. You have to think here, will you be just attending the invasion? (11am) The parade? (3pm) & after parties? (5pm++++) I typically choose to wear jeans, it’s still cool enough to not feel grosso. Also, you don’t look like a dirty pirate when evening rolls in. (Walking around downtown + of Tampa in skirts/shorts, you’ll get mud, dirt, yucky stuff on your legs.

Shirt: Tank top, strapless, cardigan, pirate themed tee, will all work. There will be sun, think about your shoulders!

Jewels: I like glitter & shiny things. Pirates like booty after all ;)

Etc: Sunscreen, TP & hand sanitizer (porta-potties), backpacks filled w/ snacks + flasks, sunglasses!

Some advice from my good (& more stylish) friend Lindsay:

Having gone to Gasparilla pretty much since I was a fetus, I’ve got knowing what to wear and what to bring down to a science. If you are a wanderer, like me, who enjoys trekking several miles up and down Bayshore to party hop, comfy shoes are essential! I also like to make sure I have a large purse to carry around my booze, bottles of water, and my beads when they get to heavy to wear.

Rather than going full-on “pirate”, I’m a fan of a more subtle approach. These are two options using black and white striped tops and skull accents. The one on the left is more casual and appropriate for walking, and the right would be better suited for viewing the parade from a house party or VIP tent.

Gasparilla Wench

If you see yourself as less of a pirate and more of a wench, this outfit has a vintage and feminine feel, with a dress that gives a nod to a traditional pirate shirt, boots that would be perfect for pillaging and plundering or walking along a parade route, and a wide brimmed hat to protect you from the sun.

Are you going to Gasparilla? What will you be wearing?