There's something liberating about breaking out of your comfort zone, even if it's in small doses. For someone who abides by all the rules, never shows up late, and thrives in painfully monotonous routines, I'm not exactly what you'd call a risk taker. The same can be said about my taste - though I'm certainly not immune to an occasional fashion faux pas, I do know my style and rarely stray from pieces I know will work.
That's why I surprised even myself a couple of weekends back with a purchase: I bought my first pair of Birkenstocks. I'll admit that after reading this Vogue article, they suddenly became more appealing, though still an eyesore. But I'd been searching for a sandal that was easy to throw on and also provided some support, and these fit the bill.
Of course there's a certain amount of judgement that goes along with buying into a trend that was never considered fashionable, especially when it seems slightly out of character. In fact, one friend said, "Ha, I can't believe you're wearing Birkenstocks."
But fashion, above all else, should be fun. It should excite you to try new things, experiment with different trends, and go outside your comfort zone, every now and again.