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Against all odds, you just got yourself a date. It may have taken over twenty attempts before someone finally said "yes," and a few of those attempts may have been marked by such supreme awkwardness that it physically hurts you to recall them, but one of them worked, and that's all that matters. So, honestly, the hardest part of dating is already over. In that light, figuring out what to wear shouldn't be so bad. Let's start with the DON'Ts and move on to the DOs.

What Not to Wear

The context of the date is important in determining how formal or how casual you should go, but either extreme should be avoided. That means no full suit and oxfords, but also no flip-flops and a muscle shirt. In fact, cut out the entire lower tier of casual wear. That means no short pants, and nothing more casual than a fitted, newish, solid t-shirt. Dressing down is much more dangerous than dressing up. You want to be yourself, but not yourself when you're passed out on your couch and covered in Bugles crumbs on a Saturday morning.

Try this Blue Star Custom Shirt from Tien Son
This might seem obvious (it isn't to some people), but you should never wear anything that's faded, ripped (even with little pinholes from the washer), pilled, wrinkled, too big, or too small. If you aren't willing to splurge for an entirely new outfit, pick the best maintained clothes in your closet. And be sure to check for pit stains, because they are noticeable. If you're wearing new clothes, wash them at least once with nice-smelling detergent before wearing them out.

What To Wear

With 80% or more of your closet ruled out, you may be wondering what exactly you're allowed to wear on a date. The truth is, you have a lot of options - you just may not own as many of these items as you have t-shirts that you got for free. Believe me, I understand.

A buttoned shirt is the absolute best way to go. Science says that both men and women find people who wear red more attractive, but this may not be true for everyone, especially redheads. Blue is a much safer color and is a better option if you're just getting to know someone. It's more flattering on most people, and it's relaxing.
A very sexy sweater. Great winter option from Tien Son.

Speaking of relaxed, you should wear your sleeves rolled up. You will look significantly more youthful and less uptight. And jeans are a perfectly fine option, as long as they are medium to dark wash. None of those light Wranglers that make you look like you either own a singing bass or collect vintage dolls. Dress pants are also a great option, especially in ultra-flattering black. Well-tailored dress pants in a dark color will draw the eye upwards, hopefully all the way to your face since that is where charming words will be coming from.

As far as accessories, ties are alright but not recommended for everyone. If worn, they must be dark and skinny. You want most of the attention to be on you, not what's around your neck.

If it suits your personality, and if the location of the date is appropriate, a vest is a nice addition that will make you look put together and fashion conscious. And if you're whimsical and can get away with it, go ahead and throw on a bow-tie. Particularly if you're taking your date somewhere like this. If you take your date here, though, you're just deranged. Not whimsical at all.

What did you wear on your last date? Any regrets or recommendations? Tell us in the comments!

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