Why don't you get an inexpensive trendy look one to wear and see how you feel? I've been seeing this trend come back for a bit now, but I also think it's all in what you feel comfortable with. Some are really confident and would feel awesome bringing this trend back, while others may feel it's taking them back to their school days way too much. Me personally, I'm not sure. Maybe if it was LV or Chanel lol.