The season-five finale of Mad Men a few nights ago ended with a brief chain of events that threatened to decimate the central premise of the entire season—namely, a new Don Draper: less work-obsessed, more monogamous, and less haunted (literally) by demons from his past.
Despite the revelatory plot twist, it was hardly shocking to see classic Draper reemerge—and beguile the best-looking ’60s mod-era minx in the bar, and her friend, without even trying.
What was unexpected, though, was this season’s occasional loosening-up of the definitive Mad Men uniform (trim suit + white shirt + narrow tie). Secondary characters came into their own, style-wise, and even Draper and Roger Sterling relaxed a little. Read on for our top five less-buttoned-up looks of the season.
1. Off-Duty Don. He wore this timeless, casual-yet-polished combo to the office—on a Sunday. Take a cue and make an effort, even when you don’t have to. Shop V-Neck Sweaters.
Shown: Etro | Kenzo | Dockers
2. “Dinner-Party” Roger. Couldn’t resist including this scene of Sterling, in the bath with his quasi-estranged second wife, hallucinating that he’s at Yankee Stadium. Directly prior, he was talked into trying LSD by a group of hippie intellectuals—while wearing a perfect navy blazer and power tie (Sterling’s version of ‘casual,’ as opposed to his standard three-piece suit). Shop Navy Blazers.
Shown: Hickey Freeman | Psycho Bunny | Hugo
3. Stan Rizzo’s Stripes. Mad Men nails all the differences—in personality and attire—between account men and creative types. Rizzo, an art director, makes casual-staple polo shirts look office-ready on a daily basis, thanks to a trim fit and clean lines. Shop Polo Shirts.
Shown: Rag & Bone | Gant Rugger | Boss Orange
4. Harry Crane’s Adventurous Side. We decided to pass up the vibrant, prep-staple plaid dinner jackets donned by Draper, Cosgrove and Campbell early in the season, and instead focus on the subtler, but still statement-making patterns that TV-exec-schmoozing Crane has caught on to. Shop Plaid Sportcoats.
Shown: Hart Schaffner Marx | Psycho Bunny | Hart Schaffner Marx
5. Ginsberg’s Creative Streak. The new guys’ clothes are like his thoughts: scattered, a little messy, but inevitably a glimpse of brilliance shines through. His pattern-mixing here is a travesty, but his printed shirt is as on-point in 2012 as it was in 1967. Shop Novelty-Print Shirts.
Shown: Etro | Eton | Kenzo
[Individuals pictured do not endorse Nordstrom or products shown. Images courtesy of AMC and Lionsgate. Don, Stan and Harry via GQ.com; Roger and Ginsberg via polentical.com.]