Off-Duty Steez: Don Draper's Best Looks Outside of the Office

Well before Justin Timberlake tried to, Don Draper inspired countless dudes to get on their suit and tie shit. We understand the importance of having a suit in your wardrobe, but we're more about the off-duty sartorial fire that Don brings. Since Mad Men came on the air in 2007, all we've heard is how sharp Don and his colleagues looks in a suit.

It turns out that, on the weekends, on vacation, and at home, Madison Avenue's favorite ad man is just as stylish as he between 9 a.m. and 5 p.m. Because style doesn't clock out, here are Don Draper's Best Looks Outside of the Office.

Season 5, Episode 5

If you get dragged into attending a co-worker's dinner party that you want absolutely nothing to do with, there's only one thing to do: show up in an awesomely outrageous jacket and stunt on your underling in his own home. Then fix his sink and emasculate him in front of his wife. Don does both by showing up in a look that 100% embodies the "fuck you" attitude he not-so-secretly harnesses toward Pete Campbell. Workers of the world, take notes.

Season 1, Episode 3

When Sally Draper's birthday party rolls around, Don doesn't bother getting suited up for the occassion. Instead, he comes through about 12 drinks deep in his day-long bender—too many to tie a knot, but still able to throw on a black knit polo under a midnight blue blazer.

Season 1, Episode 3

For his daughter's birthday, Don puts together a playhouse in the backyard. Doing such strenuous work requires two things: a white tee and a shitload of beer. Besides his pre- and post-coitus gear, this is the most casual look we've ever seen from Don. Rocking the white tee and khakis channels his inner Stanley Kowalski, much to the delight of Betty and her friend.

Season 3, Episode 13

When you're one of the hardest working men/drinkers on Madison Avenue, you need some downtime at the crib. Before A$AP Yams coined the phrase, Don Draper was living that cozyboy lifestyle in the '60s. In a worn-in flannel and loose trousers, there's not a man among us who wouldn't drift off into a well-deserved nap.

Season 1, Episode 13

In one of the best scenes of the entire series, Don takes the good people of Kodak down Memory Lane as he clicks through personal photos on what he dubs The Carousel. The pictures hark back to better times, when hot dogs were shared (pause) and Don rocked a yellow PJ collar shirt with a contrast placket and trim. The bouclé piece was classic '50s style, and as fresh as any of Don's suits.

Season 2, Episode 11

When Don jets out to Cali for a work trip and to visit old friends, he knows that his stuffy NYC suits won't fly on the west coast. And this is especially true when he falls in with a crew of self-proclaimed nomads. So, he opts for a navy polo with white piping. The open collar and casual look certainly works its charms on Joy, the Cali bombshell that had her eye on Don since he touched down poolside.

Season 2, Episode 7

In case you didn't have a picnic look set aside for the upcoming warm weather, this is what you should wear. The olive, maroon, and navy color scheme is subtle, and doesn't look like you put on any sort of picnic costume. But it's also relaxed enough to lay down and snooze in the shade.

Season 2, Episode 6

At the Memorial Day event at the local country club, the Don Draper shows up in an outfit that's perfect for kicking off the summer. A spread collar, dusty blue polo with glen plaid pants and a simple watch is all he needs to stunt on the rest of the country club set. This outfit isn't loud, and confidently states "wealth" rather than screaming it.

Season 3, Episode 2

If you were debating whether you were for or against short sleeved shirts, Don Draper merked the look and that's all that should matter. With the exploded plaid pattern and flat hemline, Ossining's biggest womanizer captures the attention of Sally's schoolteacher, getting an A on the D and on the outfit.

Season 6

This is a promotional photo from Season 6, which debuts tonight. Not much is known except for the strong rumors that Don and his wife are vacaying in Hawaii. If that's the case, this is exactly what you'd wear while brooding over an old fashioned at a tiki bar in paradise. Who knew that Don Draper had a Reyn Spooner shirt in his wardrobe?