I never liked spectators and didn't understand how anyone would wear that, its just something you don't see anywhere i've lived, yesterday I saw a young guy in the mall wearing a pair of wing tip spectators with jeans, supper cool. They are not for me, i would be too conscious but the do look great. Good combo mimo
Firstly, it's kind of always summer where I live, so canvas spectators are a comfortable semi-formal shoe. And secondly, like Rikod said, it's really about how you feel in them. I have that bit of "in-yer-face" about me sometimes, and despite being neither young nor cool (41 next month, with the appearance of permanently digesting another human being), it seems to work for me. I like to dress smartly, rarely wear jeans (although bright red ones for a party this evening - in yer face!), and like to offset the formality with a little dash of eccentricity here and there.
Whatever works for you, really. But I've a real weakness for the specs, and there will be more!