Wearing smart-casual clothing makes me feel like an eccentric, even a misfit, but I cannot bring myself to fit in by looking as slovenly as some of my cohort do. I'm a graduate student and many of my peers seem determined to dress as casually as they possibly can. I was in undergrad about a decade ago, and I have to say that my undergraduate peers often dressed with more care and sophistication than the teaching assistants in graduate school do today. I find it dismaying, especially as my group frequently has the opportunity to meet renowned individuals. Is it not rude to wear gym shorts and a baseball cap to meet someone who has won the Pulitzer Prize, for example? I think so, anyway.
I get varying reactions to my look. In general, I'd say that looking groomed, made-up, and alert benefits me. I find that professors, visitors, and other people of that stature are more likely to engage me in conversation than a sloppily dressed peer. However, something as mundane as wearing a daytime dress can elicit questions about where I am going and why I am so "dressed up". I do get compliments from some women, generally the women who put some care into their own dress and presentation. The women who do not see any reason to bother seem to have a "who do you think you are?" attitude though and it doesn't help relations any that dressing in a feminine and groomed manner draws male attention my way.
It would be nice if people could make fewer value judgments based on one's style of dress, but I suppose that's not going to happen. I do sometimes feel the victim of reverse snobbery, as if the harder I try to look nice, the more friction I will encounter from people who have long ago decided that almost no occasion is worth bothering over. Oddly, some of these ultra-casual folks are not oblivious to their appearance. They may diet, work out at the gym, get tattoos, or dye their hair. But they certainly have a different sense of appropriate dress than I do.
Sometimes I get to feeling so self-conscious that I change into a less attractive outfit or remove a unique piece of jewelry. Or I'm afraid to add some of the more flamboyant accessories that I love. It's always a balance. I know I will get some positive attention for looking nice, but I also know that looking nice alienates those who choose to look as if they just rolled around in a rag bin. I sometimes think it would be easier to get away with my style of dress if I was shorter, straighter, or had mousy coloring. But my natural looks draw the eye anyway, so I do worry about looking vulgar when I wear something that flatters.
A little neurotic, huh?