This is skeptic7. I love in the first story, that Coulson is prepared for Steve's entry with clothes and all. I am surprised that SHIELD didn't send Steve out with a personal shopper, someone who would explain clothes as camoflauge. This is how to dress older, this is how to dress younger, this is what a working class man in his 20's would wear, this is what a young professional wears to work. This is clothes for a night club with a young affluent audience. This is what college age wear at college, at leisure at parties. Don't try to figure out what high schoolers wear. Now if you wanted to look like a pervert .... This is what to wear to look like FBI, really its fun to let them catch the blame for everything.
this wouldn't get anywhere near dressing to express yourself, but it would keep Steve from being as lost and they have experts in this available, well they did have experts before the Alien attack on New York. Natasha knows all about clothes as costume to fit in a particular group.