Can someone help with my wardrobe? I'm so confused.

Please. I'm very confused in this world of fashion. 100% lost. I used to have a girl friend that literally took me out to get clothes. Like everything from underwear to dresses. She always picked out sexy clothes or stuff that was too tight, I guess to show off curves, but it just kinda hurt.

Now I'm kinda lost. My current girlfriend literally picked out some jeans 2 months ago, and I kinda just have that my dead moms t-shirts and my old boy clothes. I figured out the underwear part. I just need help with the rest please.