Some or all, may think I'm crazy wearing ugh boots (liked it at one point in my life) in the middle of summer on Guam! Yes, that sounds stupid because for one it's an island and two it's normally always 80+ degrees but I would normally wear it at night and only when it rains. So it tend to be a little bit cooler but still no one would wear it when it's 70+ degrees. The point of that was I wore what I loved and how I felt in it at the moment.
Another time would be when I wanted to express my inner asian style. I'm not sure if this phase really has a name for it but that's what I'm going to call it. I was really intrigued by the style in Asia. I guess I thought, since I am asian I thought I'd embraced it a bit more. It was more of a topping to what I already liked. I just tweaked and maybe changed my closet a bit. In the end of this phase, I realized that it was always a part of me (no pun intended) BUT I was still missing something about my style.
Present moment, I can actually say I am who I am and I love the style that I've created for myself because it's me. I always knew I had a SnapBack obsession and a mix match closet (meaning, I would always gravitate towards very unique pieces of clothing but nothing seemed to match in my closet, that I love). I can be a bit extereme to some and a bold to others but I've gain so much confidence just by this acknowledgement that this is who I am and I love me for me. It wasn't an easy and simple step to take in this century because we have magazines telling you one thing, maybe your parents or best friends telling you another, and most of the world portrays beauty by an outward appreance then the inside.
So when I think of what I want to wear for the day, I simply think of who I am and what I love. I also consider respecting my body and those around. I like to leave mystery. I don't want to make it easy for anyone to read me but don't get me wrong, sometimes you can be easily judged by wearing whatever it is no matter what. This is just my personal style and how I like to present myself.
Don't give yourself a hard time when it comes to style because it shouldn't be like that. Explore till you feel right with what style you like. If you want to think outside your comfort zone and try something out, GO for it. If it doesn't work out, you'll know. Don't let people bring you down about how you dress.
If I really had to give just one advice (other then what I just shared) my first thoughts would be, try everything at least one time. Then you would know what works best for you and who you truly are in your own style.