There is something universally magnetic about pirates. They represent freedom, rebellion, adventure, and, let’s be honest, really great fashion choices. For as long as I can remember, the call of the Jolly Roger has been a consistent fun point in my life. It started with toys, evolved through movies and video games, and eventually manifested in an increasingly elaborate series of costumes.
Today, I want to take a walk down memory lane — a plank down memory lane — to trace the history of my interactions with pirates, leading up to what I consider my “final form” pirate aesthetic this past Halloween.
The Foundation Years: Bricks, Muppets, and Airships
My fascination didn’t start on the high seas; it started on the living room carpet in the early 90s.
Lego Pirates (Early 90s)
Before Jack Sparrow made eyeliner cool, there was Captain Redbeard. The Lego Pirate theme was absolute gold in the 90s. I spent countless hours building ‘ships’, staging mutinies on deserted islands (the couch cushions), and burying plastic gold doubloons. This was the spark that lit the fuse. It taught me the essential visual language of piracy: peglegs, hooks, parrots, and tricorne hats.
Muppet Treasure Island (1996)
If Lego provided the visuals, the Muppets provided the soundtrack. To this day, I would argue that Tim Curry’s Long John Silver is one of his greatest cinematic performances. This movie perfectly blended the adventure of Stevenson’s classic with absolute absurdity. It taught me that being a pirate could also be hilarious. “Cabin Fever” still makes me get up and dance.
Treasure Planet (2002)
Just when I thought I knew everything about pirate stories, Disney released Treasure Planet and completely redefined the genre for me. This film took the classic Stevenson tale and launched it into “the Etherium,” blending 18th-century sailing ships with futuristic solar sails and cyborgs. As someone with a deep affinity for world-building, seeing John Silver reimagined as a complex cyborg with a mechanical arm—which was basically a Swiss Army knife of pirate tools—was mind-blowing. The emotional core of the movie, paired with the soaring soundtrack and John Rzeznik’s “I’m Still Here,” spoke to my creative side in a way few movies have since. It proved that the spirit of piracy wasn’t tied to the ocean; it was about the horizon, wherever that might be. Not to mention my love of all things tech and robots at the time made this movie strike true.
Skies of Arcadia Legends (GameCube, 2003)
Following that theme of sky pirates not stuck on the ocean, Skies of Arcadia on the GameCube blew my mind. As Vyse, an Air Pirate, I wasn’t just sailing; I was captaining a flying ship, recruiting a crew, and exploring a vast uncharted sky. It proved that the spirit of piracy—exploration and freedom—was more important than the water. I have vivid memories of overnights at a friend’s house playing Skies of Arcadia all night long.
The Ultimate Immersive Experience: Pirates of the Caribbean
Of course, no chronicle of my pirate journey would be complete without mentioning the legendary Pirates of the Caribbean attraction at Disney. This ride has been a constant thread throughout my life. I remember the wide-eyed wonder of riding it as a child, being mesmerized by the “Yo Ho” melody and the smell of the bayou.
Now, as a dad, the experience has come full circle. Getting to share that same magic with my wife and watching our five kids react to the cannon fire and the skeleton-filled caverns is a highlight of every trip. For someone who values melody as much as I do, that iconic theme song is the gold standard of atmospheric music. It’s an immersive masterclass that has fueled my lifelong fascination with the genre more than almost anything else.
A Brush with Reality
The Vasa Museum – Stockholm, Sweden (2007)
All my life, ships were things of plastic or pixels. That changed when I visited the Vasa Museum. Standing in front of the Vasa—the world’s only preserved 17th-century warship—was a humbling, awe-inspiring experience.
While technically a Swedish warship and not a pirate vessel (it famously sank on its maiden voyage in 1628), the sheer scale, the smell of the old wood, and the intricate carvings grounded all my fantasies in reality. This was real life. People actually lived and worked on these massive wooden beasts. It added a layer of historical appreciation to my fandom.
The Campus Swashbuckler: My College Reputation
By the time I reached my college years, a certain collection had become a defining part of my social identity. It wasn’t long before I earned a bit of a reputation on campus; many knew I was a “pirate.” But I shall say no more but let your imagination expand with this image as it’s a little off theme.
A Romantic Raid: The Honeymoon Dinner Theater
Even the most romantic trip of my life—our honeymoon—wasn’t complete without a bit of swashbuckling flair. I’m incredibly lucky to have married someone who accepts my pirate affinity. We made a point to visit a pirate-themed dinner theater in Orlando, spending the evening cheered on by acrobatic stunts, booming cannons, and a meal fit for a captain. It was a hilarious and high-energy way to kick off our marriage, and it set the tone for all the themed adventures we’d go on to share as a couple.
The Sartorial Evolution of a Scallywag
While I was consuming pirate media, entertainment and exhibits, I was also occasionally trying to become one. Looking back, it’s a clear timeline of escalating commitment to the bit.
The Early Years (Childhood)
We all started somewhere. My first pirate costume was a striped shirt, a plastic hook that was incredibly uncomfortable, and a cardboard sword wrapped in aluminum foil. Patch the Pirate was all the rage!
The Cruise Era Begins (Pre-Kids Cruise, 2014)
As an adult, I realized that cruises were socially acceptable venues for grown-ups to dress like pirates without question. Thankful on Disney cruises it’s encouraged for one night a sale. Pirate Night! On our pre-kids cruise with my family, I allowed myself a little fun. Just a free costume, but it was my first attempt as an adult.
The Vallier Family Cruise on the Big Mickey Boat (June 2019)
By 2019, the operation was expanding. On a family cruise on the “Big Mickey Boat”, it wasn’t just me; we were building a crew. The costumes were getting better, the accessories more plentiful. There’s strength in numbers, and walking the deck with a whole squad felt right.
A Brief Detour: The Dread Pirate Roberts (Halloween 2019)
Later that year, I took a specific detour into a beloved niche of piracy. I traded the traditional captain’s coat for the all-black ensemble of Westley from The Princess Bride. It was a fun challenge to embody a specific, iconic character rather than a generic buccaneer. “As you wish…”
Another Throwback Period Pirate (Couples Cruise, August 2024)
On our couples’ cruise in August 2024, I decided to move away from the traditional “Captain” aesthetic and pay homage to a character that defined pirate-adjacent cool for my generation: Rufio from Hook. As someone with a deep affinity for 90s nostalgia, stepping into the shoes of the leader of the Lost Boys was a thrilling challenge. I focused on the iconic “Bangarang” swagger. It felt less like a costume and more like a tribute to the rebellious spirit that drew me to pirates in the first place.
The Final Form (Family Halloween 2025)
And that brings us to this past Halloween. This was the culmination of over 30 years of R&D.
This wasn’t just a costume; it was an assembly of curated pieces collected over years. The weathered tricorn, the heavy frock coat, the flintlock pistol replicas, the intricate belts. But the best part was that my whole family was decked out alongside me. We were a full pirate crew, from the captain down to the smallest swabbies. Almost, the youngest is Tinkerbell but Tink was pirate in a former life. I did my best to mimic Will Turner from Pirates of the Caribbean.
It’s been a long journey from plastic bricks to full privateer regalia, but I wouldn’t trade a moment of it. Now, where’s that rum gone?