9 Outfits You Should Never (Ever) Wear on a Date

Stripper heels and micro-shorts

I went on a date this summer with a girl wearing short shorts and four-inch heels. It was like she got distracted halfway through getting dressed and forgot to finish the process—and the result was über-trashy. Not exactly take-home-to-Mom material.
—George, 29

Distracting (and potentially dangerous) accessories

The only time I was on a date and I thought, What was she thinking? was when the girl showed up wearing a Gilligan-esque bucket hat and strange cloglike shoes that she tripped over the entire night. The major takeaway from this story: Don’t wear anything below the ankles that was inspired by the Dutch.
—John, 22

All your favorite trends—at once

My date once wore Uggs, a long, giant wooden beaded necklace and big, bug-eyed sunglasses. Worn separately they might have been fine, but together it spelled disaster.
—Matthew, 29

Whale-tail-flaunting pants

Thongs: They have their place. But that place isn’t five inches above low-riding jeans. Belts were invented for a very, very good reason.
—Glenn, 35

OshKosh B’Gosh-inspired gear

I would be mortified if a girl showed up to a date in overalls. I can’t think of any legitimate occasion—outside of milking cows—where that dress code would be considered appropriate. And if our date did involve milking cows, I think I have bigger concerns than what she’s wearing.
—Stephen, 23

Harem pants

Those weird high-waisted pants that get wide in the legs and then taper at the ankle? Those are the worst.
—Joe, 28

Fluffy, frilly stuff

I met a cute artsy chick while visiting a friend in San Francisco and invited her to go wine tasting in Napa. While I’m not sure there’s a dress code for wine tasting, she definitely broke some rules: Her ensemble consisted of Sherpa boots and a gigantic wool poodle skirt. I spent the entire evening trying to convince myself that heads were turning because of my date’s stunning beauty, not her hideously fluffy outfit.
—Rob, 26

Athletic gear at non-sporting events

Girls can look adorable in a team jersey, but preferably with sweats or boy shorts. But when we go out at night, it’s better to keep the 88-covered sports gear at home.
—Rick, 39

Glitzy, trendy overkill

I met this amazingly attractive girl at a concert, but on our first actual date, she showed up in the skimpiest jean shorts, leather high-heeled boots, a shiny tube top and—the clincher—sparkly flesh-color leggings. I was totally embarrassed because this date was a daytime lunch outing, not a night on the town! The thigh bling is what really killed it.
—Vincent, 38

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