No judgments here. Below, five otherwise stylish individuals work through their biggest fashion missteps for the new book, "I Actually Wore This: Clothes We Can't Believe We Bought."More
"I dress a lot like the history teacher that everyone likes, even though he's a tough grader."
Regrettable Article of Clothing: A "Jazz Forever" T-shirt
Purchased: Gift, 2013
Times Worn: 3
"If and when I become an old guy on the Upper West Side, I shall wear my shirt proudly as I sit on a park bench, doing the Sunday New York Times crossword in pen."
"Once a year, my friends and I have a weekend where we all go away together. The destination changes, but one thing remains constant: each of us must bring a ridiculous outfit."
Regrettable Article of Clothing: Pantsuit
Purchased: New York City, in 2013, for $200
Times Worn: 1
"It is two pieces and something I thought Megan Draper would buy with some of that divorce money. I practiced putting it on quickly so I could maximize the element of surprise. I had gotten my time down to under ten seconds. Yes, a grown woman with a job and everything was doing this."