Should i were this on my date?

I like the vest and T with a dark wash long jean. Take into consideration what your doing for your date. Try to pick something your comfortable in. You dont want to be messing with your clothes the whole night. And try to stick to something close to your normal style. He has seen you before and agreeed to this date for a reason, he likes you. So dont be throwing him completly off with a new you. Have fun!