Big cities always encourage more bold fashion choices. Who cares if you look different when there’re millions of people walking the sidewalk every day? It’s a bit dramatic to describe the way anyone dresses as “brave”, but I really do appreciate when people feel they can express themselves freely through their clothing.
Tokyo is up there when it comes to the best dressed cities. Residents of all ages aren’t afraid to throw bright colors or unconventional cuts into their outfits. Japanese clothing in general allows for much more flexibility than American fashion. We have shirts, sweaters, and jackets. They have giant scarves, three-quarter-sleeved jackets, and drapey poncho things. I was there in late October and caught a lot of cool overcoats and layers.
Check it out and learn from the best.