Do you dress to avoid pain or to bring pleasure? I really believe that these are the only two motivations behind people's sartorial choices. The people who dress to avoid pain (whether it's physical or social discomfort they're avoiding) are purely reactive. Their clothing decisions are always AGAINST something, never FOR something, and it drives me nuts.
I just want to go up to those poor lost souls, like some dress missionary, and ask "Sister, did *anything* about what you're wearing today make you happy? Or was it all about avoiding the possibility of unhappiness?" If you want to go to Chicago, you don't get there by going away from St. Louis, Cincinnati, Detroit, and Milwaukee … you get to Chicago by going towards Chicago. If you want to love what you wear, you can't get there by just avoiding things that other people hate, or that you fear they might criticize. Someone's always going to hate what you're wearing (and if it's culottes, or a Juicy Couture tracksuit, that person will be me).
The first time you wear something you really, truly love, something that gives you so much joy you don't even care if blind people cross the street to tell you it's ugly–something really interesting happens. When you wear something that's really yours, that shows who you are, and not just what you're afraid not to be, people react to the truth and the honesty more than they react to the actual clothing. Funnily enough, most people LIKE truth, and they LIKE honesty, and at some gut level they recognize that you're becoming more yourself, and they give you compliments. Often, lots and lots of compliments. Even if it's something they'd never, ever wear themselves — say, a skirt covered with multicolored polka dots that looks like nothing so much as a slightly repurposed Twister mat and a blaze-orange hoodie — they still recognize the joy behind it, and they respond to that. And not just people you know. Strangers on the street (yes, even in New York City) will stop and compliment you. (And there's nothing as nice as random validation from strangers!)
Wearing what you love is not all a Mentos commercial, though. Occasionally someone will not only hate what you're wearing, but go out of their way to tell you so to your face (as much as I hate Juicy, it would never occur to me to tell someone SPECIFIC, in PERSON, "I hate your Juicy tracksuit and everything it stands for." That's just plain rude. Hate the sin, love the sinner, invite the sinner dress shopping; I may disagree with what you wear but I defend to the death your right to wear it, etc., etc.) Just by wearing what you love you will have built up such a store of happiness that such comments just drift by you like dandelion fluff. Especially when (as is so often the case) you see that what THEY are wearing was designed by Fear for the Fear Fall 06 Collection, with accessories by Fear. Why should you take someone seriously who doesn't even dress to maximize happiness?
If you're unsure whether you're dressing for joy or out of fear, here's a test. Picture your favorite dress. Picture yourself running into someone wearing the EXACT SAME THING. If you think, upon seeing your doppelgnger, "OMG, I have to go talk to her, I bet we would get along great"? Joy. If you think "Oh, hell no, bitch better WATCH OUT"? Fear. Easy-peasy. (I can get you a wallet card with this on it if you want.)
Click on the image to check out this joy-giving, life-affirming dress (B38/W31, with a SAILOR COLLAR) — in fact, somebody please buy it before I do! My closet is too full of joy already …