Most Helpful Girl
1. Good fitting dark jeans
2. Band t-shirts that you like, funny t-shirts, vintage shirts (stay away from Affliction)
3. Buy a casual suit jacket (H&M has them at all price ranges)
4. If your shoes are falling apart just buy new ones already, black shoes go with anything.
If you're unsure about matching just buy earthy tones like blue, green, black, brown.
(This is just my opinion of what looks good, take it with a grain of salt. Don't lose your personal style. All girls have their own personal preference.)