I love spectator shoes. I have a pair of black and white cap toes and a pair of brown and white wingtips. However, I just never have the opportunity to wear them.....or perhaps I should say that I rarely feel that it's appropriate to wear them as they are so flashy (or at least will be perceived as such). For those of you who have and love spectators, when do you wear them, and with what outfit do you wear them? Hopefully your stories will help me be brave enough to wear my spectators more often!