The two things that can hurt you are if you need money or if you need fame. Those are the things that can be your Achilles heel. But if you don't need money and you don't need fame, then you're free.
I feel like shoes are one of those things that no matter how conservative or how outrageous you get, a good pair of shoes is going to last you a lifetime.
Remember, America's greatness is based on creating wealth like the rest of the world has never known, and then, making sure it's shared throughout a middle class and even the underprivileged.