How to dress like Roger Sterling in Mad Men
Is Roger Sterling better dressed than Don Draper?
Roger Sterling is one of the most charming and unlikeable characters on the hit TV show Mad Men. He's well-dressed and often witty, but at the same time he's a total flake who's dragging down the rest of the advertising firm with his inability to do anything of significance other than get drunk and make inappropriate passes at Joan (Christina Hendricks).
Played by John Slattery, Sterling is one of the central figures in Mad Men and is also the most impeccably dressed. I'm going to give a run-down of what he's often seen wearing on the show so you can attempt to try the look yourself. Just please, for the love of God, don't try to imitate his manners.
Roger Sterling's 3-piece suit
To best duplicate the Roger Sterling look, you're going to need a 3-piece suit in gray, preferably a lighter gray. Avoid charcoal gray, because Sterling is known for wearing lighter colors. The classic suit that fits the Sterling look is the Brooks Brothers 1818. It's a versatile suit that can be worn on many occasions. I believe it generally runs around $600, and you'll probably want to budget in a couple extra hundred to make sure you get it tailored to perfection. The true key to that Mad Men look is absolutely impeccable tailoring. Fit is far more important than brand names.
The Roger Sterling dress shirt
It's hard to tell exactly what brand dress shirt Sterling usually wears, so I'll have to make an educated guess. It's an Oxford dress shirt, that's for sure. It's usually white. Since he's in New York, let's just assume it's a Hickey Freeman. Hickey Freeman is a small menswear manufacturer that caters to the bigwigs, usually in the NYC area.
Roger Sterling's Tie
For the tie, go with something darker than the dress shirt (not too hard, since the shirt is white) and lighter than the gray suit. Sterling is known to wear light blue often, so go with that. The tie should be somewhat on the skinny side, but not a true "skinny tie". Sterling was not a hipster.
Measure the width of the lapels on your suit and that should be about the width of your tie at its widest point.
Sterling's pocket square
Pocket squares are simple. Match it to either your shirt or your tie. You can buy them in either silk (preferred for the Sterling look) or cotton. Make sure to fold it properly (use Google to figure out how). I buy all mine at The Tie Bar, a site you should know and love. $5 for a regular size pocket square and $8 for a large one. That's hard to beat.
We don't see Roger Sterling's shoes much, but I can assure you they are dark gray or black bluchers. You can buy a blucher just about anywhere. If you are going to wear these a lot (like if you have a good job and aren't just putting this ensemble together for a costume or a night out on the town with your buddies) you should consider getting a nice pair as they'll literally last you decades if you take care of them properly. Unlike gym sneakers, a good pair of bluchers don't wear out after a year. There are also people who repair shoes like these for a living, which is something you can't really do with your rubber and plastic Nikes.
The Roger Sterling watch
The watch that Sterling wears on the show is a Cartier Roadster. This watch runs about $5,000, which is a little high if you're just trying to mimic a look. There are many cheap alternatives, and nobody is going to notice if your watch isn't a perfect match for Sterling's. Really, any silver watch with a silver linked band is going to work as long as it's simple and doesn't have too many complications and dials (like Breitlings or some Citizens are known to have). Remember, Sterling is an advertising executive, not a navy pilot.