There are no hard and fast rules about what you must wear on a first date. There’s no dress code and there is no one way of dressing that will impress any date that you may have. The main rule when dressing for a first date and any subsequent date is to dress properly for the specific occasion. Keep in mind the environment that you will be in with your date.
The problem with wearing a t-shirt on a first date is often that it is worn casually to a place that is not supposed to be casual. If you are taking a date out to dinner, it is possible to wear a t-shirt the right way in order to be appropriate to the occasion. The trick is to dress the t-shirt up or down according to where you and your date will be headed for the evening.
If you’re going to a picnic or a sporting event, wearing a t-shirt and jeans is certainly appropriate. If you are going out for a nice candlelit evening, you can still wear a t-shirt as long as you pair it with dressier items. If you wear a jacket or blazer over your t-shirt and pair it with a nice pair of pants, your t-shirt will look perfectly dressy and very appropriate for a nice first date. For women, pairing a t-shirt with a nice set of jewelry will make it look far dressier. That way, you can look dressed up and still remain in a comfortable t-shirt.
If you are going for a casual date, you should still pay attention to how your outfit coordinates. Don’t wear a t-shirt with the clashing pair of pants or a scarf that doesn’t match your shirt. Put together your outfit with care so that it flows well. Try to color coordinate so that your t-shirt is part of a well-thought-out outfit.
No matter where you’re going to no matter how casual the event is, it’s important that your t-shirt should be clean and in good condition for your date. Wearing a dirty or rumpled t-shirt is a sign of disrespect and will not impress your date no matter how casual the date is supposed to be. To show your date that you respect him or her and that you have made an effort with your appearance, hang up your t-shirt the day before you wear it so that any wrinkles will have the chance to fall out. You might also consider ironing your t-shirt so that it looks its best.
For any date, wear a t-shirt that is not stained and does not have a collar that is stretched out. If you want to wear white t-shirt for your date, wear one that is not dingy has been taken care of properly. If you can show your date that you made an effort to look your best even for a very casual date, you will have done your part to make the date a success.