geos are going to look huge most of the time but i find they work well with the detroit cut jeans in my opinion. otherwise, I usually just wear them with over the knee socks from AA or heat tech tights and shorts. i too love wearing my prisoner pants but make sure you size down 1-2 as they fit huuuuuge. if you have instagram, you should look at @oliverdoor or @meninrickowens for some inspo.
the sweatshirt looks good but if you do decide to size up for a slightly oversized fit, i don't think it'd look bad either.
Thanks man. My jeans are all Detroit from RO, are you tucking the tongue of the geo under or are you putting the Jean stack over the top?
Also I'll check the Instagram users thank you.