Baggy clothes like sweats and basketball shorts are meant for wearing when participating in athletics. If you would like to wear them at other times, keep it in your home.
People you've seen:
Nina Newman
Henry Benschoter
Peter Rees-Eissler
Accessories that don't match aren't very pleasing to the eye. When wearing an accessory of one color, try to incorporate it in your look at least one other piece.
Dressing for winter while it's summer, or dressing for summer while it's winter is just dumb, not to mention you look very out of place. Your outfit may be cute, but please save it for the right season.
You've seen:
Abigail Boswell
Deborah Zachgo
Darrion Williams
Wearing similar shades of denim is awkward, and not very pleasing to the eye. If you want to wear multiple pieces of denim, try drastically different shades.