My whole sentient life I have been pretty adamant about the way I wanted to look. While, in my case, this hasn't equated to tattoos or even dyed hair, I've certainly made some experimental aesthetic choices. I've never really understood the sense of fear some people have when it comes to wearing things they deem "risky", or even worse "unflattering". Aesthetic decisions about yourself seem, to me, the only creative process that absolutely every human has to partake in. So making these decisions from a place of uneasiness, compromise and even fear can only really set you up for unhappiness, both in how you look and in how you are. I often receive comments such as: "Wow, that is some lipstick. I wish I could pull that off." Well I have news for you -- all of you. You can.
To be able to "get away with" something all you need is belief that you can. Once you start to really understand this, it's like Dorothy's realization in the Wizard of Oz, that she had the power to get home within herself the whole time. You tell yourself you can wear it, and you can. It's really the closest thing to magic which exists in the world. If you pretend you feel confident about your choices, eventually you will.
The trick lies in an arrogant sense of trust in all your aesthetic decisions. Take it as read that you have impeccable taste. Therefore, everything you decide you would like to wear will look great, simply because you have chosen it. This takes away all of the unnecessary and fun-destroying agonizing out of your decision making. If you like it, you are right, and you should wear it. If you don't like it, you're right, and you shouldn't. You're right. You are right.
I am prone to indecision and self-doubt in pretty much all areas of my life apart from my style-based decisions. I don't think I've ever avoided something I actually wanted to wear for fear I couldn't "pull it off." I'm 5'9, and I wear huge clumpy shoes all the bloody time. Having self-confidence which borders on the bratty in this small but important area of my life acts as a foundation for the other areas. Putting on a "risky" lipstick, or shoes which makes you 6 foot 4, tricks everyone around you into thinking you're completely self-assured and confident in every way, and not just in your makeup-based decisions. I obviously don't care what you think of me; otherwise I wouldn't be wearing this ridiculous [insert item here]. And it can even trick you.
There are many who focus on the concept of "flattering" when questioning aesthetic risks. To which I say: you are totally missing the point. Most brightly colored lipsticks are, in the basest sense of the word, deeply unflattering. They are jarring and loud and obnoxious and FUN. Neon pink doesn't "go" with any other color, really. That's not why it's enjoyable to wear. If you admire it on others, you can definitely "get away with it" yourself. It doesn't "suit" anyone, so conversely it actually "suits" everyone the exact same amount. Self-excusing language doesn't make sense to me: simply by wearing it you are "getting away with it," you are "pulling it off."
My perspective on these things has led people to believe I am "fearless." I'm not fearless at all -- I'm scared of lots of things: strangers, sharks, throwing up on airplanes. But I'm just not scared of clothes or makeup. There's no bravery in wearing something "out-there," really. Doing it once (maybe twice for beginners) is enough to convince you that there's no need to be scared. For the most part, nobody around you will notice, and if they do, it is seriously unlikely they will care. And even if somebody else doesn't like it, you shouldn't care. Everybody knows that you can't please everyone, but you can guarantee that wearing what you want will definitely and consistently please you. And that is powerful.