When I only had my one pair, Converse were just starting to shed their association with the "goth" crowd in middle school, and my 2003 self felt that I needed to prove my distance from that group's classification, wearing the black low-tops with slightly flared jeans and a velvet blazer ("business" on the top, casual on the bottom). I wore them with shorts and skirts and just about any outfit you wouldn't expect a sneaker to go with. When I went for my white ones, they were meant to be more of a statement. They were intentional. I paired them with white jeans and a white v-neck t-shirt and dresses that called for a much more formal shoe. I stumbled upon the slim-soled high-tops sometime in 2011, and stalked them for a while. I waited too long and they stopped making the off-white kind, so I just went for the original, and I'm so glad I finally gave in.
My high-tops offer more variety than I could ever expect. From chambray shirts with jorts and sweater/shorts combos to rolled up skinnies with lots of layers to a leather skirt with my new Boom sweatshirt plus swingy dresses, maxi skirts and just plain keeping it casual (on gameday, go Wildcats!), they're shockingly versatile, but in a way I also anticipated (which is why I stalked them for so long, I guess).
Converse are the best. There's almost nothing they can't go with outfit-wise, and sometimes just the prospect of wearing them with an outfit gets me excited. I thought they deserved a shoutout.