All Dressed Up
If the two of you have chosen an upscale restaurant for your date, you’re going to want to dress up. This doesn’t mean you have to put on your best suit and tie, but it does mean that you’re going to have to take some time in piecing together your outfit.
When you’re going someplace upscale, you want to forgo wearing anything like jeans and a t-shirt. If you’re thinking of wearing a blazer over your Green Day t-shirt and black jeans, think again. This type of dress won’t cut it and you’ll stick out like a sore thumb. Instead, you should consider wearing something as simple as a black trousers and a button-up shirt. You can wear a tie if you want, but it’s not necessary. Make sure you have on dark shoes and give them a good polish if they’re old. If you have a blazer, you should definitely consider wearing it, but if not, you don’t need to rush out to buy one. Finally, make sure you are wearing a pair of dress socks, not socks. There are few things worst than being dressed up and then ruining your entire outfit with some bulky, cotton socks.
Dressed Down to Perfection
If the two of you have opted for someplace more common and less expensive, you can dress down a bit. While we would still urge that you avoid wearing any t-shirt, you can opt for a simple polo shirt with a color to show her that you still care about your appearance and making a good impression with her. You can wear jeans, but we recommend making sure that the jeans are dark blue or black and that are ones you do not wear very often. Try to avoid wearing jeans with holes in them or ones that have frayed over the years.
If you have your heart set on wearing a t-shirt and jeans, you should probably make sure your first date is at a rock band concert or at a local sporting event. While t-shirts are comfortable, they don’t generally make a good impression on a first date. Also if you do wear a t-shirt to one of these events, you should definitely skip wearing muscle shirts or shirts that are two or three sizes too small. Even if you are well built, it won’t give off the effect you’re going for and your date may end up secretly laughing at you.
A tip to help you figure out what to wear is to ask her what she’ll be wearing so you’ll be able to spot her. You can then piece your own clothing together based off of her answer.