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Halloween can present a challenge for a well-dressed man—especially now that the “Don Draper” costume is well past its expiration date—but we’ve got a solution for you. It involves monocles…

The menswear canon has a lot of items that are both fantastic in a “deep trad” kind of way and completely ridiculous in any normal setting. This is your chance to see what you can do with them. And thanks to the pandemonium of style that will going on around you, you’ll look good pretty much no matter what.

Here’s a good place to get started:

The Bowler Hat
Possibilities: Alex DeLarge, Sherlock Holmes (Downey, not Rathbone), Charlie Chaplin

This one’s our favorite—in fact, we’re holding out hope that one day we’ll be able to wear ours under non-costume circumstances. Costume or no, good haberdashery is good haberdashery—and a fine-looking hat will never serve you ill. Of course, finding one that fits can be difficult, but if you’ve already got one in your closet, now’s the time.

The Monocle
Possibilities: Col. Mustard, Mr. Peanut, Tyler Brûlé

Whether it’s dangling from your waistcoat or nestled over your eye, the monocle is an exceedingly elegant way of saying, “I’m kidding.” More importantly, they’re all over eBay, so you should be able to pick one up for, well, peanuts.

The Ascot
Possibilities: Fred (of Scooby Doo), an Anonymous Gentleman of Leisure

One man’s style overreach is another man’s costume. Find a velvet blazer—maybe a pipe—and you don’t even need a costume. You‘re just an unusually classy version of yourself. Don’t forget the cologne.

—R.B.

CONTRIBUTORS

  • Russell Brandom