Funny Stuff

Fashion File: The men's underwear of Mad Men

As Mad Men wraps up its final season, let’s look back at the men’s underwear that defined a generation of style. No other show has so captured those classic styles, those iconic looks, those timeless trends in men’s underpants.

As Mad Men wraps up its final season, let's look back at the men's underwear that defined a generation of style. No other show has so captured those classic styles, those iconic looks, those timeless trends in men's underpants. When the series debuted in 2007, it set off a cultural shockwave of appreciation for the Y-fronts of yesteryear. So let's drop some trou, and take a closer look.

[Spoilers within]

Even hungover and overcome with regret, Don Draper knows how to cover his man-parts with style. Actor John Hamm may prefer to go commando, but he's in top form here in a classic pair of dingy, shapeless boxers. It looks like Don Draper knows how to take his own advice: "Make it simple, but significant." And he certainly has!

Don Draper isn't the only one who knows how to package his package. Stan Rizzo is seen here in a very different pair of plum smugglers: briefs, aka tighty-whities. Stan may be lazy at the office, but he sure put his thinking cap on when he dressed his pelvis. Note the high-rise of the waist, and the way the lower fabric playfully draws the eye to the lumps in the front, proving without a doubt that Stan is the man.

Here's Don in another iconic pair of boxer shorts in a delicate off-white. (Dare we say ivory?) These shorts prove Don's not just another pencil pusher; he knows how to get stuff done… like smoking while painting a wall for the wife of the dead man whose identity he stole. Don may neglect his family and his health, but he never neglects looking fab below the abs.

Roger Sterling is Mad Men's resident silver fox. We don't know if the curtains match the carpet, but they sure go well with these silk boxers. Note the elegant way his shirt flows into the boxers like one seamless cascade of underwear. The lesson here is that top quality speaks for itself, and never be afraid to accessorize your look, whether it be a pair of jaunty garters, or an affair with your secretary. Roger? Copy that!

The last word - and look - goes to Don Draper, our sartorial hero of the nether regions. Here we see him frantically pulling up another stylish pair of wang wranglers, right after his daughter Sally catches him in the act with another woman. Awkward? Not with these easy-on undergarmies. And in the hands of an ad-man like Don, those boxers aren't just groin gauze, they send a clear message: "I love you, I wish you hadn't seen that, and as soon as I've got my Johnson covered, I'm going to make everything okay." Stay classy, Mad Men. Always.

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