Top 10 Worst Date Outfits

Would you wear sweatpants to a fancy restaurant? What about flip-flops and shorts on a first date? Read about these and other hilarious dating fashion disasters from both men and women below…

By Diane Mapes

few years ago, a friend of mine went on a blind date, and the minute she walked into the restaurant, she spotted a guy sitting alone wearing one of those green yodeler’s caps — complete with a feather sticking out of it. “Don’t be him, don’t be him, don’t be him,” she whispered to herself,
She didn’t want to be on a date at a nice restaurant with a slob.
desperately scanning the room for another single male diner. But, of course, it was him — jaunty six-foot-long pheasant feather and all.

While some people are convinced that a person’s clothing doesn’t affect interpersonal chemistry, what you wear actually does count if you’re trying to make a good impression — particularly on those crucial first or second dates. Herewith, we present a few tales from the trenches about dates gone awry due to clothes that should have never left the wearer’s closet.

Top five worst date-night looks for men...
Fashion disaster #1: Sloppy sweatpants
During her dating days, Stephanie B., a 39-year-old events manager from Seattle, WA, recalls once having gone out with a man who looked like he’d just come from the gym — only in 1989. “He showed up wearing sweatpants,” Stephanie says, “you know, the old-school kind that cinch at the ankles? So sexy!” (Not.) What do experts have to say about the sloppy sweatpants look? “When a guy wears sweatpants, he’s sending a message,” says Judy McGuire, author of How Not to Date. “Mostly, it’s that he doesn’t care enough about impressing you to wear pants that require him to suck in his gut to button them up.”

Fashion disaster #2: Flip-flops and shorts
Dating coach Julie Spira says that she’s heard plenty of complaints from both men and women about first-date attire. “But men,” she says, “are usually more… shall we say, fashion-challenged.” Case in point: A client of Spira’s was recently asked out to dinner by a promising guy. Since he chose a fancy restaurant, the woman went all out, looks-wise — hair, makeup, a nice dress, everything. So what was the problem? “He showed up in shorts and flip-flops,” explains Spira. “My client walked in and was completely upset.” Spira says that while dressing like Jimmy Buffett may be comfy, it can also definitely alienate your date. “She didn’t want to be on a date at a nice restaurant with a slob,” she adds. “So, she walked out on him. They never made it past the appetizer course.”

Fashion disaster #3: Pet fur-covered clothes
Ann J., a 41-year-old human resources professional, loves animals — but that doesn’t mean she wants to hang out with someone covered in fur that’s been shed by their own beloved pets. “We went for a walk on our date and he was telling me about the loves of his life — his cats,” she says. “Then, he pulled a bunch of their fur off of the fleece jacket he was wearing and offered it to me, as if it was some lovely prize. Um, what?” McGuire (who has cats herself) understands how pet fur can infiltrate a person’s life, which is why she has an easy antidote for this type of situation. “I’d recommend keeping at least one date outfit in a shrink-wrapped bag somewhere safe,” she advises. “Otherwise, you may end up with someone going into anaphylactic shock from a cat allergy during your date.”

Fashion disaster #4: Gold chains/a half-unbuttoned dress shirt/too much cologne
“Unless it’s 1977 and your name is Tony Manero, leave the gold chains at home,” says McGuire, who points out that this isn’t just a major dating pet peeve for her, but for almost every single woman alive. “Gold chains, overly unbuttoned shirts and an abundance of Axe body spray are most women’s triple-threat — as in ‘three strikes, you’re out,’” explains McGuire.

Fashion disaster #5: Women’s undergarments
Tess M., a 40-year-old Seattle accountant, says that she was on a first date with a guy who suddenly leaned forward and made a startling confession she could’ve done without. “You’re never going to believe this,” he said conspiratorially, “but I’ve got women’s panties on. See how far I’m willing to go for a conversation starter?” Tess was mortified. “It was more like a conversation ender,” she recalls, who adds that she left shortly thereafter. While women’s lingerie may have done wonders for Nuke LaLoosh (Tim Robbins’ character in the movie Bull Durham), it may not do much for you on your first date, warns McGuire. “If you enjoy cross-dressing, that’s great,” says the Brooklyn-based author, “but unless I’ve already mentioned that I’m a fan of it, you should probably wait until I actually decide I like you to let me in on your little secret.”

Top five worst date looks for women…
Fashion disaster #1: Ugg boots
Yes, they’re still somewhat trendy (but why, we’ll never know). And yes, they’re quite comfortable, but Spira says that these furry caveman boots are a huge dating don’t for
She was dressed like I always imagined that ladies of the evening would be dressed.
men. “A guy will say, ‘She looked really cute, but those Uggs just don’t do it for me,’” Spira explains. “I’ve heard it over and over again.” Spira says women should definitely wear these kinds of slouchy boots while running errands or hanging around the house, but it’s best to leave them in the closet when it’s time for a date — unless you’ve been dating a long time and don’t mind being “sweatpants casual” around each other. “Guys don’t find them to be feminine or sexy,” Spira says. “They’d rather see a woman wearing a sandal or high heel — or for that matter, even flip-flops rather than Uggs.”

Fashion disaster #2: The Pretty Woman-inspired look
Christopher R., a 44-year-old writer from, Lexington, KY, says that he’ll always remember his first (and last) outing from an online dating site because of the woman’s terrible outfit. “She was wearing a full-length fur coat, thigh-high leather boots and what appeared to be a pajama top,” he recalls. “This was August, by the way, and it was about 90 degrees and very humid outside.” Not only was the woman excessively sweaty the whole time they were together, she was also just plain scary — despite her pretty looks and promisingly vast collection of books, according to her profile. “She was dressed like I always imagined that ladies of the evening would be dressed,” Christopher says.

Fashion disaster #3: Showing off too much cleavage
Men like curves, to be sure, but they don’t always like them shoved up into their faces — not on a first date, at least, insists Spira. “Guys will say, ‘I met this great woman but I had a hard time talking to her because she had huge breasts and wore a low-cut dress. All I could do was stare and wonder if they were real or not,’” she says. “They’ll never even get to know that woman, because they’ll never ask her out again.” It’s not that men don’t want to have sex, says Spira. They do — they just don’t want to sleep right away with women whom they might want to marry someday, explains Spira, adding: “Don’t dress for the bedroom on a first date!”

Fashion disaster #4: Long, fake fingernails
They may seem elegant to some devotees, but Spira says that those long, artificial fingernails can actually scare the life out of many single men. “Guys have told me: ‘My date was really pretty, but I took one look at her nails and thought she was going to scratch me to death,’” says the L.A.-based dating coach. “Have your nails manicured, put on a nice color for the season and stay away from anything neon, ladies,” advises Spira. “That’s trendy and fine for a girl’s night out — but it’s not a good look for a first date.”

Fashion disaster #5: A wedding dress
“I once went on a second date with a woman who actually showed up in a wedding dress,” says Jose C., a 25-year-old entrepreneur from Miami Beach, FL. “I turned pale when I first saw her, but then kind of let it slide. We were at a rave, and other people were dressed in all kinds of semi-bizarre costumes.” Unfortunately, the woman in white kept trying to hold his hand and called him “babe” all night long. “My friends have never let me live that night down,” Jose says. “They still ask me how my ‘wife’ is doing.”

Diane Mapes is a Seattle freelance writer and the author of How to Date in a Post-Dating World. Check her out at or follow her on Twitter: @Single_Shot.
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