As an 18yo college student, I think I have a different perspective that could help the conversation. So, I go to college every day basically and there's always people (typically women) in pajama pants, sweat pants, or those tight yoga pants (I don't mind those at all ;P). It's like everyone has two sides to themselves: the sloppy styleless side that doesn't care and the side that cares too much and puts on a dress and makeup for no reason. Personally, I don't have a sense of style, I've always been a quiet kid, never had many friends so I was never on the "style train" as they call it. I always wear plain Eddie Bauer t-shirts with basketball shorts and a pair of training shoes. Lately I've been experimenting with the cold weather, I hate blue jeans because they're so darn uncomfortable. Every time I sit down with blue jeans, my dangly bits are squished (maybe TMI lol). I've been experimenting with these new sweatpant type things called joggers and plain nike sneakers, and I have to say it is extremely comfortable. And I don't feel like an idiot walking around as a 250lb man in basketball shorts and Nike training shoes in 35 degree weather. So there's my $.02, take it as you will.
Edit: Wanted to add, I'm born and raised in Louisiana, so I'm familiar with the boots and jeans wearing type. Basically I'm saying that I grew up with the option of boots and jeans without looking outta place, just never chose that route.
Sent from my SM-G950U using Tapatalk