This is an easy genre to do, but a hard one to do well: making fun of men's fashions of the past. Something Awful just raised the bar with this installment of "Fashion SWAT":
Also in the same vein: James Lileks' review of fashion house Dorcus (no, really.) And my own stab at writing about men's fashion
Go read this right now.
Zack: "Women will attend to yachting duties, men will gather at the ship's fore section for a 9 minute smiling break." Where do you think they're sailing today?
Dr. Thorpe: The Isle of Plaid.
Zack: I think they're headed for the Isle of Plaid.
Dr. Thorpe: Clearly we can't use that joke, because it's too easy.
Zack: Obviously, so where do you really think they are sailing today?
Dr. Thorpe: Well, I actually really think they're sailing to the Isle of Plaid, honestly. I mean, there's no getting around that one.
Also in the same vein: James Lileks' review of fashion house Dorcus (no, really.) And my own stab at writing about men's fashion