. The Worst Things to Wear on a First Date |

Oct 12 2012

What Not to Wear on a First Date

Published by at 9:00 am under Editorial

It’s a common mistake for guy’s to think they have to win the girl over with their style on a first date. While it’s important to look good, do you really think that chick’s going to bend over and let you go to town because you’re dressed like F’in James Bond? Absolutely not.

But since it is important to look good, it’s just as vital to know what you shouldn’t be wearing the first time you meet up with a girl. Our girlfriend still remembers what we wore on the first date – most chicks somehow do – so you’d be best served going with something subtle, sticking to your style, while avoiding any of these fashion mistakes.

Black Jean Shorts

A pair of jorts is bad enough, but when you bypass the navy blue ones for black, it just makes it that much worse. Do you want the first impression this girl has of you to think you live in a trailer park with your parents, and most likely have incestual relations with your cousin? Probably not, so stick to some classy jeans or khaki shorts if it’s hot out.

Shirt and Tie

Unless your first date’s at a wedding (highly unlikely), there’s no reason you should be rocking a tie. In fact, this speaks volumes to both yours and her personality. If on a first date you’re going somewhere classy enough where you both have to get this dressed up, than you’re playing it all wrong dude. Keep it simple, and stick to biz casual the first time you meet a chick. We know you want to make a good impression, but try something a little different.


We all loved Air Jordan’s back in the day, but the sneakers should be kept for pounding the pavement after a day at work, or crossing fools up on the hardwood. We’re not saying we have the best style, but we do know that pairing jeans or khakis with the wrong pair of shoes can make you look like an absolute clown.


You are straight, right? Kidding (kind of). But if there’s even a question from us, than what the hell’s the girl going to think? Exactly. We like to wear scarves too. They keep you warm and can be a great accessory in the winter, but unless you’re taking this girl to the Arctic Circle for your first date, keep it bundled up in your closet. A worse scenario is you show up with one, she doesn’t, and you look like a bigger pansy than your date does.

Something Resembling This

Anything that shows unwanted body pubes is sick. Even if you have your buddy shave you do down every other morning (you know who you are), that doesn’t give you permission to go ahead and wear something that makes people question if you have serious brain damage. It can be funny, but it won’t be on a first date, trust us. Needless to say, you’ll be sleeping alone that night.

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