Going on a first date is exciting, nerve-racking and brings lots of pressure. We’re not trying to beat around the bush here, guys, because you know that the second you see your date face-to-face, you both will be judging one another hard, wondering why she decided to layer on so much makeup, while she’s concerned with how much cologne you’re wearing.

Obviously, once you sit down together and start talking, we hope those physical judgments fade away and the rest of the night goes well, but, as you know, a first date is all about making a good first impression — and your clothing will be the first thing she notices about you. That’s why it’s crucial to wear something that expresses your personality and atmosphere of the date without coming across the wrong way.

For those guys who no longer have a mom to lay out their clothes before school — or, in this case, a first date — we’re here for you. So keep on reading to see what outfits no man should wear on a first date, unless he plans on having the girl immediately be turned off.


You want to look your best, and if you toss on a hat, that will not be your best. We don’t care if you’re insecure about thinning hair and don’t want her to judge how the light finds a way to shine off your dome, if you wear a hat, it’s showing her that your self-confidence is already bad. Whether you’re thinning or not, go in confident and style your hair. For those who might think they need a haircut prior to the first date, that’s usually a sign that you do, so get things cleaned up and put your handsome self out there for her.

Flip flops

No. No. No. Flip flops should be kept in the closet unless you’re with your family on the beach for vacation. Hell, even then we’re not huge fans of the things. Like other items of clothing on this list, flip flops show laziness or a mentality of being too casual, and that’s not the look your date wants when you meet up for the first time. Put in a little effort and go with some clean sneakers or dress shoes, depending on the occasion.

T-shirts or sweatpants

First off, sweatpants to a first date is basically a slap in the face of the girl you’re meeting up with. Not only does it show laziness on your part, putting forth zero effort to look good, but there’s a good chance that she’s put together, and then has to (embarrassingly) spend the evening with you. Not cool.

As for t-shirts, there are some exceptions, but, for the most part, we advise always going with a button-down or polo. You’re a gentleman who’s on a first date, so put your best foot forward — even if the day is at an amusement park or beach. Show her that you’re different than other guys who would’ve gone with the easy tee look.

A bunch of jewelry

If there are things you wear regularly, like a bracelet or two, that’s fine. But it can become excessive when you’re wearing more jewelry than the girl sitting across from you. After all, you’re not a mob boss who needs to wear flashy things to get attention. Remember, you want the focus of a first date to be on you, not what you’re wearing around your finger or neck. Plus, if it’s too gaudy, there’s a good chance she’ll try to ignore it during the night, then go laugh about it with her friends afterwards.

Gym clothes

It may be 90 degrees outside and humid as all hell, but that dri-fit shirt is meant for running, not a first date. Not only does it show you put little-to-no effort into your first date outfit, but, hell, the girl may wonder if you either just came from the gym — which means she’s probably thinking you smell bad. The two of you may, one day, be comfortable enough to get to that point, but it won’t be on the first date.