Most Helpful Guy
I have not been in the dating scene in quite some time. However I would base what you wear on a few factors. What you are doing initially when hanging out, where you may be going, meeting his friends or family, time of day, temp, season, festivity and so on. Don't go crazy with getting super fancy. Something casual, a bit flashy that is just enough to keep catching his eye, don't dress to the nines otherwise you will leave no interest with him to wonder how well you can really get dressed up for a more formal occasion. Not to heavy on make up. Just some accenting. Jewelry again not to heavy. Nice ear rings, necklace and rings that are not going to take away from you. Dress cute. No sweatshirts or t shirts. A nice fitting snug but not tight top. With color. Maybe a little bit fancier jeans. Tight pants are ok as long as they fit you well and not to to tight. You want to leave some for his imagination. You want him to want to see you more and his desire to see you more dressed every time. Hope this helps.