I think one of the most hard things to do is to know what to wear to a date, but I think that the most important thing you have to do is to always be comfortable with the outfit you are wearing, try not to think a lot about what the other person is going to think, think more about you being comfy and feeling good, here are a few outfit ideas for you to try, this is something I would totally wear:
1. I would wear this to a brunch/luch kind of date or even just to grab a coffe/drink.
5. And the final one, perfect for going to the club or going out with his friends.
Lots of love,