"How do you deal with an audience uninterested in fashion? I find it difficult sometimes to explore the outfits and styles which challenge and intrigue me without leaving a gap betwee my look and my fellows'. Balancing fashion to the occasion is important, but should I just let go and accept that I will dress differently than my crew? This seems like it might be even more common in male friend circles."
Rabbit, I think it becomes a matter of degrees. I like the Texas-flag cufflinks I wrote about as an example. I wear them with a suit and tie and cap-toes, but they are cheeky and colorful and a little flashy, and they still fit the scene I'm in. Wearing a bolo tie, while cheeky, probably would not fit.
Within that thought, I think you just have to go with your instincts on how much you can push in a given situation. Fashion and style are socially mediated. Thus, the presence of one stylish person in a crew will encourage the others to take small risks. The small risks succeed and incrementally increase the crew's confidence, which in turn fosters more risk-taking and success (with the occasional failure).
Likewise, the presence of a vast majority of people who do not wear acid-washed jeans with little mirrors embroidered onto them, and have not since the '80s, will encourage the handful of people who have such jeans not to wear such jeans.
I think runway shows are a pain in the ass because they set up this "high culture/low culture" dichotomy that just doesn't exist in real life. Wear what gives voice to yourself, and if you can wear it with confidence, the confidence will carry just about anything you can buy in a store--in part because your confidence is by definition a product of your environment, and in part because personal charisma can sell a look that would otherwise be outre.