Some lessons in being Fancy, brought to you by Fancy Pantalons, age 8-10ish.
Lesson #1: Go with what you know, and go for broke; less is never enough, and more just barely cuts it. Demonstrate your passion for impeccable music and a "street" attitude with a tasteful patch featuring the name of your favorite boy band from Boston over your left front pocket.
Lesson #2: Fortune and fashion favor the bold. Sport unfortunate pairings (e.g. socks and sandals) before others realize they're a no-no, thereby remaining always pre-trend. Sunglasses convey an uppity sensibility, so choose frames in a friendly color. Always accessorize with a small child, preferably several (plastic children will work in a pinch).
Lesson #3: Fashion does not exist in a vacuum. It's important to contextualize, and nothing says "I'm successful!" more than a nod to the institution that facilitated your greatness. Ties to patriotism should not be too overt, however; a grimacing visage tempers the grandiose surroundings, telling the onlooker: "I care. But just a barely appropriate amount." Be always attentive to body language: arms crossed, legs in fifth position say: "Don't mess with me, I sort of know ballet." When in doubt, pink tights.