Every once in a while I like to go off-trend and try a different look just for the fun of it. And to see if I can pull it off.

I’ve always wanted to give the ascot a shot and when I was invited to a wedding this weekend, I seized the opportunity. I wore a simple silk black ascot instead of the usual bow tie with my tux (see the Blind Bunny Black Teardrop Ascot). To my great relief, it was met with hardy approval. The female guests thought it elegant and dapper—and daring because, after all, I did risk ridicule. The male guests envied the way it comfortably coddled my neck, especially compared to all those tightly knotted ties and buttoned-up collars. And no one said I looked like Thurston Howell, III.

There are three keys to rocking the ascot. First, you must choose your style models carefully. Think Al Pacino in the Godfather. Think Fred Astaire or David Niven. In more recent times, think David Beckham, Jeremy Piven, and Andre Benjamin.

Second, practice wearing it around the house so that when the grand occasion arrives you’re not pulling or tugging on it as if it’s a foreign object.

Third, it’s all about context. You can wear an ascot to a fine restaurant like Fleur de Lys in San Francisco, to lunch at the Four Season’s in New York City, to a Vegas show, or to formal affairs like weddings—any place where the crowd is sophisticated, tolerant of eccentricity, and stylish rather than stodgy. You should not wear an ascot to your grandmother’s birthday party.