Jess at Sea

Working as a Disney Cast Member over the past seven years has been a magical ride – and one of many costumes! From the magical charm of Main Street, U.S.A. to the enchanted pixie dust halls of the Bibbidi Bobbidi Boutique aboard Disney Cruise Line, I’ve had the joy (and sometimes puff-sleeve challenge) of wearing some truly memorable Disney costumes.

In this post, I’m sharing the most iconic costumes I’ve worn throughout my Disney journey – what they looked like, what made them special, and how they brought each role to life. ✨

🏰 Emporium Costume – Main Street, U.S.A. (Magic Kingdom)

My Disney story began with the Disney College Program, where I worked merchandise at the Emporium on Main Street, U.S.A. Talk about an iconic start!

This costume was pure vintage charm: a plaid dress straight out of the early 1900s, with puffed sleeves and a big apron to match the turn-of-the-century Victorian aesthetic. In winter? You’d find me bundled in the biggest puff-sleeve jacket ever – retro and completely appropriate for Florida heat haha! #PlaidLifeForever

✨ Fairy Godmother-in-Training – Bibbidi Bobbidi Boutique (Disney Cruise Line)

One of the most magical roles I’ve ever had! Working at the Bibbidi Bobbidi Boutique on Disney Cruise Line was like stepping into a storybook. The costume? A whimsical purple waistcoat with lilac accents, bows, and a sparkling wand.

🏴‍☠️ Pirates League – Pirate Night Transformation

Every Pirate Night aboard the ship meant one thing: the Bibbidi Bobbidi Boutique turned into the Pirates League! Cue the bandanas, bold stripes, and swashbuckling flair. This pirate-inspired costume was SO fun to wear – think pirate bandana adventure meets family-friendly fun. My pirate name was Jess the Mess, and she was pirate fierce.

🚢 Merchandise Team – Disney Cruise Line

While working in onboard merchandise, my costume was all about nautical professionalism – crisp, clean, and cruise-ready.

Though not as sparkly as my Boutique outfit, these costumes reflected Disney Cruise Line’s signature maritime style. Still magical – just in a more subtle way!

👩‍✈️ Officer Whites – Entertainment Integration Manager (Disney Cruise Line)

This is the costume. As an Entertainment Integration Manager, I wear formal officer whites – and let me tell you, I feel boss lady vibes every single day.

This role (and this outfit!) symbolizes everything I have worked toward in my Disney career: professionalism, leadership, and a front-row seat to making magic happen across the ship. I never put this costume on without thinking, Wow, I’ve really made it.

👗 A Magical Wardrobe Full of Disney Dreams

Each of these costumes tells a story – a chapter in my career, a role I got to step into, and a magical moment I helped create.

From welcoming guests on Main Street U.S.A. to creating fairy tale transformations at sea, every Disney Cast Member costume I’ve worn has been more than just a uniform. It’s been a symbol of the dream career I’ve been so lucky to live.

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Disclaimer: Disney Cruise Line is the only cruise line I’ve worked for, so I can’t speak of the experience with other cruise lines. All opinions in this post are my own and not affiliated with Disney in any way.

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