I held "Take the road less traveled" as a sort of mantra growing up, and a lot of the habits I established were based on that. Over the last 5 years or so, I've been revisiting this, as taking that adage to the extreme has gotten in the way of my ability to fit in or interact with people, and left me as the odd one out more often than I'd care to count. As always, it's important to express yourself be comfortable with yourself and how you carry yourself, but that's as good as common sense. It's also important to not distance yourself too much from the people around you, even in mannerisms, behaviors, and appearances; in order to communicate and relate, we need to have some common ground with other people. That's true for many aspects of our lives as social creatures.
A friend of mine once told me "Act like you're the shit, because even if you aren't, people will believe you are. People won't second guess you, because they're too busy second guessing themselves." Whether it is with your style of dress, your choice of vocabulary, your interests, or whatever if may be, confidence that it's who you are or what you enjoy is key. If you don't feel that confidence, then you might consider adjusting things until you do. Push the line a bit toward something, and if you still feel comfortable, go for it. If not, you know where to stop.
The same friend also spent some time a few years back reinventing her clothing style, as she was preparing to enter the professional world. In her case, she looked to others, and cribbed elements of their style that she liked and was comfortable with, and made them her own. She was really fond of the traditional styles of Arabic and Indian women, so she incorporated modest, colorful patterned skirts, and nice solid-color blouses and such. She's also rather tomboyish, so she used headscarves as both a way to manage her hair, and a way to add a pretty, decorative element to her attire. All in all, it works well together, and she looks good in it, though what makes someone look and feel good doesn't apply to everyone else.