Recently a reader of this blog asked me for my thoughts about reviving the ascot. My reaction? My gut feeling is that I'm not a fan, but after poring over dozens and dozens of photos -- both past and present -- I'm more inclined to say that I do like the ascot, albeit on very few men. My former impression comes from seeing too many men wearing ascots in ways that just don't work: too stuffy, too literal, too nostalgic, too ambitious, etc. What I can say about the men I do like in ascots is that they wear them on their own terms, as a natural extension of their own life and style. I am also more attracted to today's men wearing an ascot in a messier way. The ascot has such formal connotations that its hard to imagine seeing one in all its perfect pinned-down glory look at home even at the swankiest of occasions in this day and age. They're better off worn in a more laid-back fashion -- under a sweater, not quite tied right, and only on a chilly morning or evening, to suggest that the ascot does in fact have a function, apart from standing out in the crowd.
Adam Heyer -- gangster, accountant, and member of "Bugs" Moran's gang -- wearing a traditional ascot. Heyer was gunned down in Al Capone's hit, known as the St. Valentine's Day Massacre. Something about a gangster in an ascot is just brilliant. Chicago, 1929.
Jeremy Piven celebrating his Emmy for best supporting actor in Entourage. I have to admit that I would never have imagined him in an ascot, and I never would have recommended it, but he totally makes it work. Los Angeles, 2006.
