"Your clothes tell the world who you are," a wise stranger told me at my friend's 30th birthday party this past weekend. Another acquaintance said, "Your clothes reflect your stage in life." (A graduate student, she proceeded to lament the popularity of skinny jeans on college students at Penn.) As I get older, I realize that my solidifying fashion sense has reflected my growing comfort with myself as a woman and with myself as an individual.
This process was a long time in the making: I grew up wearing uniforms for school--an external branding of my identity as a prep school student. For years, I wore baggy clothes (usually plaid), imitated my mother's hairstyle (a bob, no bangs), and wore penny loafers (always brown) for lack of creativity. It wasn't until my study abroad trip to London that I learned to wear clothes that actual fit me; after all, I was a stranger in a strange land, but it forced me to examine myself without the traditional comforts of an imposed identity (daughter of ---, friend of ----, student of -----).
Today, I embrace the woman that I am and comfortable wearing clothes that others may perceive as too dressy/girly/etc. (I've been told that I look like I'm going to a wedding everyday; I've also been told that it's surprising that I "haven't let [myself] go" since I got married.) While determining one's identity is a lifelong challenge, the essential thing is to listen to the self that you are now; and while one doesn't need to look ready for the runway every day, it is also important not to allow yourself to mistake sloppiness for selflessness, or fashion for an undeserved reward. Ultimately, it's not what's on your back so much as your reason for wearing it that is what people see and what defines you.