By Courtland Hickey, Owner, Chicago Costume
Last year, Chicago got a pope.
Well, technically the world got a pope—but Pope Leo was from Chicago, so naturally, we claimed him immediately.
And naturally, I made a Chicago Pope hat.
The idea was simple: combine the traditional papal mitre with the unmistakable stars and stripes of the Chicago flag. I came up with the concept, and—with my direction—my very talented staff brought it to life. The hat was a hit on social media and became my Halloween costume.
Then Southpaw, the Chicago White Sox mascot and one of our longtime clients, stopped by our store to shop for costumes and props. He spotted the hat, saw the photos I had been posting on Instagram and apparently thought, “The Pope needs better Sox merch.”
The idea and images were used to pitch White Sox ownership on creating a Pope-themed hat as a promotional giveaway at the ballpark.
I’ll admit that I was initially a little disappointed that we didn’t get the opportunity to produce all 15,000 giveaway hats. That would have been quite an order! Still, I was genuinely flattered that something dreamed up in our costume shop had inspired a major White Sox promotion.
Meanwhile, another seemingly unrelated costume adventure was unfolding.
Earlier this year, my mom—who lives in Florida and runs our mascot division—called to tell me she was buying an embroidery machine. All I had to do was go pick it up.
That sounded simple enough.
A few of my guys and I arrived at a very nice woman’s basement, which was crammed with fabric, supplies and all the wonderful odds and ends that accumulate when someone has spent years making things. Eventually, she uncovered the embroidery machine.
It was old.
It was enormous.
It was very, very heavy.
Standing there in that basement during an icy and treacherous Chicago winter, there was a noticeable amount of doubt in everyone’s eyes—mine included. But somehow, we wrestled the beast out of the basement, transported it to our warehouse and got it inside without a single injury, disaster or insurance claim.
Our employees began learning how to use it, creating embroidered patches and details for our many costume and mascot projects. Then, the White Sox came back to us.
They asked us to create a special Pope hat for Southpaw, modeled after the black-and-gold giveaway hat and embroidered with the Sox logo. They also ordered twelve finely made and embroidered versions for some of their “top people.”
Today, along with everyone else, I learned just how far one of those hats had traveled.
The Chicago White Sox presented it at the Vatican—and it was received by Pope Leo himself, a devoted White Sox fan.
The story has now made local and national news, and right in the middle of it all is a hat made by our team, on that enormous old embroidery machine we dragged out of a Chicago basement in the dead of winter.
That is the wonderfully unpredictable thing about the costume business. You never know where an idea might lead—or where one of your creations might eventually end up.
At first, I was disappointed that we didn’t make the 15,000 giveaway hats. Then I was flattered that my idea helped inspire them. In the end, we got the job that really mattered: creating a special version worthy of traveling all the way from our Chicago costume shop to the Vatican.
The ultimate payoff wasn’t producing thousands of hats.
It was making one that reached the Pope.

