Hey all! Second year university student here. I just found this sub and figured I'd pitch my question to y'all to hopefully get some advice!

I recently started getting into oversized stuff. I personally wanna go for the oversized t-shirt, messy textured hair, round glasses kinda vibe, and am only struggling with the shirts at this point. I usually just buy a size up from what fits (mediums are usually a snug fit that hug me a little, so I go large to get some baggy/flow with it). Here's the question:

What do I pair with it?

What kind of bottoms would mix well with it, but also avoid looking like the guy with a big, old t-shirt and straight-cut jeans? Do I go shorts? Jeans? Jogger pants (and if jogger pants, where do you find them? I've never found them in a store)?

I usually like to wear some form of Vans as shoes, just doing my best to match the color of them to the rest of the outfit, but if there's something else to consider, that would also be appreciated!

And finally, button downs. Flannels, short sleeves, etc. Usually when I buy one a size big, it looks a little awkward because it's structured a bit and doesn't really flow well like tshirts. Is there a way to wash them to soften/loosen them up, or a type of material to look out for?

I'd appreciate any help y'all have to offer!

Edit: wording