It's been my experience that fashion revivals leave a sort of "residue" of retro coolness that doesn't disappear entirely. My only suit probably dates back to the seventies (I wasn't born until the early eighties), but wearing it gives me occasional points for being "retro" or something to that effect. Since it doesn't stand out glaringly it doesn't attract too much attention (I think there is something to being conservative), and since I'm totally out of phase either with cutting edge fashion or any revival cycles, I don't appear to be behind the curve and struggling to keep up with fashion. I just look like an outlier that could fit into some fashion cycle associated with some subculture somewhere, or who has a strong self-identity (plus in complements my body shape relatively well, so I don't look absurd that way). But then, I only weakly interact with most social groups, and my strongest social ties are with fashion challenged subcultures anyway. In short, being way out of phase in fashion cycles (which gives one a fairly large margin of error) is relatively safe compared to being just slightly behind a fashion cycle.