In a lab, when you add an unknown, sometimes you get the cure to polio, and sometimes you get a fireball. Like in an experiment, wearing an unusual outfit can either go horribly wrong, or wonderfully right. And sometimes it’s hard to add the “chemical” because of the fear of “blowing everything up” and having people judge you for your outfit. It’s a bit terrifying leaving the house in something that you’re not sure really works.
However, I think it’s important to realize that you can wear whatever you want. I once heard a quote that went something along the lines of “You think of yourself so much more than others think of you.” I find this idea extremely liberating. When you see someone in passing, you don’t think about them for too long. You might see what they’re wearing, but if you hate it, you won’t remember it for more than a few moments. If you love it, you might remember it- so why not take the risk? No one will remember if the outfit looks bad, but if it’s amazing, they sure will.
In addition, fashion isn’t exactly the sanest thing. There are drop crotched jeans running around, and off the shoulder blouses that look halfway Pirates of the Caribbean and halfway puffy cloud. No matter what you wear, there will probably be someone wearing something wackier (read; Lady Gaga). So why not take the risk and mix patterns? Why not try a turban, or wearing a skirt over jeans? You can do anything that you want. Yeah, you might look back in a month and say “what was I thinking?” but won’t you feel better having taken the risk?
Lastly, even if people do remember your outfit, and your outfit isn’t the best, who cares? You still wore it, and did something new. And as long as you liked it, nothing else matters.