What not to wear on a first date.

Despite what your mind is telling you, there’s no agenda for a first date. 

The key is to be as relaxed and comfortable as possible and to thereby get as much as you can out of the experience. One thing that can aid you in this is what you wear. Your outfit affects you and your date, whether you like it or not. What you wear does not define you but it does convey a message about both what you feel and how you feel about the person you are meeting. Don’t fight it, plan for it.

The number one rule is to be comfortable. There is no way you will enjoy your date if you are constantly pulling up your nylons or your feet are killing you or your shirt is so tight you are sitting like an Olympic dressage champion. Wear something that makes you feel good. You can certainly ask for advice, but in the end the fact that you like the way you look is more important than your BFF’s opinion. Looking good plays a substantial role in feeling good. And if you feel good, you will project confidence and fun and you will be much more likely to enjoy your date.

On the other hand, don’t be … too comfortable. If your first date is your third attempt because the girl canceled on you twice, don’t passive-aggressively wear a sweatshirt covered in cat hair and refuse to comb your hair. If you are already upset with someone, don’t go on a first date. While it is very useful to feel at home with yourself, you also want to 1.) look good and 2.) not insult your potential mate. So sweatpants are out, as are pajamas and sweaty gym clothes. Just because you love the sweater you’ve had since high school does not mean anyone else does. Try to strike a balance between comfortable and respectful.

Don’t go for slutty. It may be that certain people are looking just to hook up and that wearing a mid-riff halter top with no bra and f&^k-me heels will appeal to that type. But if you’re looking for anything more than a one-night stand, try to refrain from showing your date the majority of your anatomy on a first date. Even if you do look hot, it’s a bad idea. This goes for men too. We don’t need to see your package framed in skintight jeans and we really, really have no interest in seeing how much chest hair you have … with your shirt still on.

Dress your part. If you are a carpenter, this is probably part of what appeals to your date, so showing up in shiny business casual might be off-putting. Although, if that’s what you always wear out of work hours, then that makes sense. The point is that you shouldn’t purposefully try to look like something you’re not. Many of us go overboard in trying to put our best foot forward on the first date, but though you are trying to convey your best self, it should still be you, not an image.

Don’t try something overly trendy. You’ve seen furry knee-high boots on TV and you buy them on a whim. Bright green furry knee-high boots. They might turn out to be your favorite wardrobe item, but if you’ve never worn something like this, they’re probably not the best choice for a first date. They are likely to make you self-conscious, which will make you uncomfortable, which will make you a less fun date. For the same reasons, don’t dye your hair for a first date or shave off your beard or wear your contact lenses for the first time in two years. Change can be good, but save it for a lower stakes situation.

Dress for the occasion. If you are going to a baseball game, keep the make-up or the cologne low-key. If you are going to the opera, don’t wear jeans. If you’re doing something physical, wear shoes that will permit you move easily and safely. If you will be sitting for a long time (at a movie, for example), don’t wear something tight around the middle. You don’t want to feel bad physically and you don’t want to stick out in a bad way. Back to the cardinal rule – you want to feel comfortable and so does your date.

Don’t wear your politics on your literal sleeve. If the two of you have not gotten around to discussing your political or religious beliefs, the first date may not be the time for you to announce, with your outfit, your undying devotion to President Obama or the National Rifle Association. Having an opinion is awesome, but if you don’t know someone well and you are trying to reduce the nerves on this whole first date thing, it’s not necessary to get their back up by loudly announcing, via orange tee-shirt, your potentially controversial viewpoint. If that’s literally all you ever wear? Fine, don’t change for a date. But if you’re doing it to get a reaction or make a point, try to chill out. How would you feel if you were strongly pro-choice and you turned up to meet a date who had an “Abortion Kills” sweatshirt on?

All this is not intended to make you overthink your first date outfit … but do think.



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Posted 08-21-2013 8:43 pm by