The worst first-date outfit fails we’ve ever heard (and how to avoid them)

“Men often go wrong by wearing super-sloppy jeans,” says Whitney Casey, cofounder of the style site FINERY. “Jeans are 100% OK for a first date, but choose them wisely—no elaborate stitching or distressing, and (most important) they must fit well. Ill-fitting jeans would make me think a man has zero clue about how to put himself together—or that I’d made a horrible mistake and was on a date with a high schooler who thinks saggy jeans are OK.”

“I recently went on a first date with a guy I met online and was horrified that he showed up in an undershirt. We had planned a day date at a lake, so it was intended to be casual, but when I saw him approaching in an undershirt, I desperately hoped for it not to be him. I must’ve given away my confusion on my face because he quickly put the shirt he was carrying on over the undershirt. (I think he may have been trying to show off his body.) I’m actually a really laid-back person, but this came off as just sloppy.” — Katie N.

“I met a guy in a volleyball tournament, so I guess I didn’t know what his style was [outside of sports] because we were all in athletic gear. Our first date was to dinner and a movie. I wore a really casual dress. He wore a shimmery purple zoot suit and top hat.” —Brittany A.

“We went on a date to a lovely restaurant, where he continued to wear his sunglasses. Not the type that change and get lighter when you go indoors—regular sunglasses,” says reader Christine B.

“I absolutely hate feet,” says Brooklyn Decker, supermodel and cofounder of FINERY. “I’m not saying you should hide them forever, but if I was on a first date and a guy was wearing sandals, I think I would be too distracted by his toes to pay attention to the conversation.”

[Editor’s note: If you’re planning a first date at the beach, then bare feet is perfectly fine. Otherwise, wear some classy shoes. OK? OK.] 

“One guy I went on a date with was straight out of the 1970s. Two words: Velour sweatsuit.” —Rebecca L.

“One time I was going out with a guy on a date that we’d been planning for almost a month. He’d saved up his money and we were supposed to go to a really nice, formal restaurant—it took me two hours to get ready. He finally pulled up at my house…and had on gray sweatpants, boots, and a T-shirt. I was wearing a nice fitted dress with heels, makeup, and my hair done. He ended up taking me to a burger place.” —Jessica S.

“I went on a date with a guy in a tank top. For whatever reason, armpit hair exposure on the first date is something I think men should avoid. Needless to say, the date was not well-received and we went our separate ways.” —Sandie D. 

“I’m not into the deep V-neck thing that some men are into these days. I can say with utmost certainty that if a man were to walk in with a deep-V shirt, it would be the first and last date for us.” — Brooklyn Decker

“My boyfriend showed up in a ‘Canadian tuxedo’ for our first date. Some guys can pull this off”—see Chris Pratt’s look in this gallery to do denim-on-denim right—“but his was pretty bad. I gave him another chance, and luckily it was a one-time thing.” — Michelle M.

“I went on a nice date to a restaurant with patio seating downtown. His pants were so tight, he had to stick his legs straight out the entire time in order to sit down.” — Christine B.

“A former boyfriend decided to wear this short-sleeved shirt (no jacket) to go to a dinner at a friend’s house when it was 10° out. He complained about being cold the entire time.” — Stef S.