10 Worst Costumes

We asked 10 notable people in our readership what their worst Halloween costume was and why.

Chad Pitt

Co-Host, Chad & Jill in the Morning

“I was the rear end of a horse costume. Let’s just say I felt as if I owed the “front end” dinner by the end of the night.”

Steve Blanchard

Media relations coordinator, Moffitt Cancer Center

“A few years ago I dressed as bubble gum. Found a Double Bubble dog bed and wore the bed cover as a shirt. People couldn’t read the front of it so I just looked like I was wearing a pink throw blanket.”

Asima Azam

Commissioner Candidate, Orlando District 3

“I was Princess Leia two years ago, I opted for the white muumuu instead of the slave bikini even though it was 90 degrees out. My buns were too hot!”

Matthew McGee

Community outreach/marketing, freeFall theatre company

“I went as a very tragic looking Dame Edna. I got so plastered that I woke up on the lawn of an unnamed government building with no wig, a ripped dress and smeared lipstick.”

Pom Moongauklang

Owner, Pom Pom’s Teahouse & Sandwicheria

“I went to a Boston Halloween ball and it was my first experience into the gay party scene. It was so extravagant and amazing. I was Marvin the Martian. I had the big giant plastic head and I couldn’t see so I kept bumping into people. And I had the worst case of camel toe.”

Judy B Goode

Entertainer

“Years ago at the All Hallows Ball, I decided I was gonna be the whole frickin [Wizard of Oz] movie all by myself! Half of me was the Scarecrow and half of me was the Tin Man. I had on a Dorothy wig with a witch’s hat. I had a lions tail I had the witch’s legs that were under the house around my waist. I could not go to the bathroom!”

Brendan O’Connor

Editor, Bungalower

“My worst costume ever was actually one of my favorites. I went as Baba Yaga and I looked effing amazing. I went to the Parliament House party and took my turn walking across the stage and nobody clapped for me. All I could hear was this one queen in the front row saying, ‘What the fuck?'”

Kori Stevens

Entertainment director, Bambusa

“Easy, peasy! It was my first time in drag! I wore a cheap red sequin dress from Ross that barely fit, a wig I found at Walmart for $10 and a pair of 6-inch black stilettos. I had no pads or stockings and my legs were really hairy. I could not walk in the shoes, so I spent most of the night sitting in a chair because I didn’t wanna walk around the Parliament House with no shoes on.”

David Matteson

Associate Curator of Education & Outreach, Orlando Museum of Art

“I went as a Cub Scout once and the shorts ripped halfway through the night. Turns out I’m not a child’s medium.”

Carrie West

President, Tampa Pride

“It was about 1997-98. I went to the All Hallows after working. I didn’t have a costume put together as I thought I may be to pooped to go. I ran home and grabbed huge poly filled boobs and a butt out of Mark’s closet. I took apart three of his costumes and just threw it together. It truly looked like hell. A little Ringling Circus jacket, leopard pants, red shirt , white face makeup, gold shoes.”

More in Features

See More