I must stand up for gear...but agree that no it is not fashionable. Can you wear it in a fashionable way...yes of course you can. I remember how horrified my father was that we wanted to wear jeans...
My 20 year old son yes wears hoodies. Not yet, as it is too warm (56 degrees) but he will. They are great for guys who are too warm. Slip a t under it in winter and you are set for -40 with a light jacket. The Nike ones aren't as stylish as others but they wash like a dream, wear extreamely well and DO NOT STAIN or wrinkle. Toss it into your backback at school, go straight to work and leave it in said backpack and then pull it out many hours later and it still looks almost fresh pressed. I'd much rather he wear something dull and still look presentable than a mess of wrinkles and stains. The Nike one I'm thinking of is brown with camel lining and the same brown embroidered logo. Boring as sin yes but not label advertising per se.
He has many different t's both gear and non gear. I much prefer the gear ones and for the same reasons. His Nike white and black or blue striped golf shirts with very inobtrusive labelling wash like a dream, wear well, last forever while still being really white and do not stain or wrinkle. Yes he has a lot of more vibrant, exciting t's but they don't look nearly as nice after a bit of time, especially as my twenty year old is not the best at doing his laundry in a timely fashion and his clothing takes a beating.
Now the few times a year he wears a suit he is totally fashionable and everything from cufflinks to belt buckle, watch and shoes are well thought out. That is not his lifestyle though and I'll take the gear on a daily basis and leave the fashionable suit ensembles for those few times a year.
I don't do sweatpants, yoga pants or jeans but I just put a load of blacks on to wash and in this load my basic boring black long sleeve t's come from Bianca Nygaard, Jones NY or gear. The gear ones tend to wash and wear better than the others but I do prefer the other two brands. A little better fit. If it is a warmth issue and totally covered up who cares which one I wear. I might as well wear gear since it washes and wears better. Are basic black long sleeve t's fashionable...no but serviceable.
Do I wear my Packers fleece out of the house? No, not unless I'm walking to the malbox in the middle of winter and it's under a winter coat that will at no point be opened. Do I wear it in the house? Definately when I'll be home alone.
I think a large part of of looking really great is being comfortable in your own skin. Thus, the blouse I got this summer that felt so me is much more flattering than a dress that was appropriate. Probably also why in my Sens hockey jersey I look and feel great while cheering on my team while attending a game. Do I think a Sens hockey jersey is my best look? Heck no! Is it totally me and appropriate while at the game, heck yes!