I really like the super-casual look.
At the time, I didn't own a pair of jeans, but I did own a suit for church on Sunday. So, I showed up wearing workout shorts and a t-shirt... Yeah, great impression. I know (now).
Eventually a polo shirt was given to me. So I wore that around with my workout shorts. At one time, Jessi's roommate, only seeing the top half of me congratulated me on finally getting respectable clothes. Of course, then she saw my shorts and proceeded to attack me for my poor fashion sense.
Believe it or not, it gets colder in Oregon than central California. So I bought a couple pairs of jeans to keep warm. Man, my stock sure shot up fast! Suddenly I almost looked respectable.
When I got accepted to grad school I decided it was time to really up my game. I bought some polo shirts and some khaki pants. I even went all out and got some dress shoes. For the first time in my life I had "business casual" outfits. Thankfully my mom and Jessi took the time to explain what worked together and what didn't.
Once I graduated and got a job in Oregon I decided to splurge and bought some khaki cargo shorts. I didn't actually get them because they look better than workout shorts. I got them because I wanted pockets. Yes, before graduating I had my wallet and keys hanging from a lanyard which I swung around my neck - no pockets needed.
I'm sure my wardrobe will continue to transform, but it really stuck me when Jessi and I were flying recently. We were traveling - a completely casual situation. Historically, I would wear warm-up pants with a sweatshirt while flying. That day I was wearing my khaki shorts, a polo shirt and flip flops. I sure looked a lot different than my "kid" self.
I like to think my choice of clothing has come a long way despite me being such a slow adopter in the clothing space.