Here are the top 10 worst outfits I have—unfortunately—actually worn:
1 Black parachute pants and a Huey Lewis and the News T-shirt.
2 Royal blue mermaid-style dress with giant, detachable sleeves. (Junior prom.)
3 Candy striper outfit. Not the sexy kind; the stained, below-the-knee kind.
4 Red jeans, red turtleneck, red belt and Princess Leia buns. (First day of second grade, naturally.)
5 Messy pigtails, dirty pajamas and a rope attached to a stretcher. I was baby Jessica, the girl who fell down that well. (Halloween costume during college in the 1990s. Worst costume ever?)
6 Acid-washed jeans and a baseball jersey with the name of my college improv group on front.
7 Ruffled shirt, bowtie and Styrofoam boater hat. (My uniform at an old time-y ice cream establishment.)
8 Tuxedo jacket and hot pink cummerbund, with cheap pleather skirt and French braid. (Senior prom: “edgier.”)
9 White shirt, black pants, sequined glove and a “little” bit of blackface. (Michael Jackson Day at school in fourth grade… no joke.)
10 The same outfit, minus the blackface. (Playing Michael Jackson on SNL… joke.)
Photo by Mary Ellen Matthews.