I've noticed that bigger leather jackets, even if slightly baggy, are frowned down upon often around here. Is it better to get a leather jacket that's very snug and then have it broken in? Or should they be perfectly comfortable from the get-go?
A lot of the tighter, more fashion-brand leather jackets are, well, tight. They look fantastic over a shirt or t-shirt, but can't really be layered with sweaters or anything heavier than a sweatshirt.