
A Mad Men Style series would not be complete without a piece dedicated to the man who gives me shivers, the delectable Donald Draper. And while I’m no expert in men’s fashion, I’ll do my best to break it down for you in straight forward terms.
Mr Don Draper is a curious cat. Brooding and serious with a hidden past, he is not the one dimensional womaniser he first appears to be. But aside from his well cocked eyebrow, there are a few key elements to Don Draper’s style that you can employ to make them weak at the knees.

We do occasionally see “sporty, casual Don”, but for the purposes of an iconic look, I’m concentrating on Professional Don. In an era when a man was not dressed without a hat, and smoking in the office wasn’t even queried, Don’s character relies on both for intrigue and mystery.

* Smooth Hair
No respectable man would be seen without a short back and sides. You can achieve Don’s look first with the right cut, (yes, you ask for a “short back and sides”) and a healthy application of pomade. Lucky for us, pomade has made a come back and can now be found at all good hair retailers in a variety of brands. Make sure to keep a comb in your pocket to maintain that smooth coif after any lunch time rendezvous.
*Slim Grey Suit
There are finer details at work here in the tailoring to achieve that streamlined 60′s look, but the basics are to look for a single breasted suit with a collar “v” that is not too deep. The “v” should end just below your pec’s, not above or way below. The suit should be slim lined, not boxy and not waisted. The hem of the jacket should finish just below the crotch area of the pant, not sit higher on the waist.
*Skinny Tie
Not as skinny as the ties we wore in the 80′s, but more slim lined than your modern version, and certainly not in pink or any crazy patterns. Stick to grey, charcoal and simple striped patterns. When tying the tie, make sure the tip of the tie ends just above the belt buckle in length, and the knot is a small or a four-in-hand knot. Stay away from Windsors or Fat Boys.
* Pocket Square
Don’s character relies on small details to flesh out his look, a pocket square and cuff links are two of his trade marks. Stick to a plain white square sitting horizontally above the breast pocket flap. As for cuff links, gold settings are much more era appropriate than silver or pewter finishes.
* Fedora
What is a man without a hat? He can hide his seedy eyes the next day, give you a sly wink from underneath or doff it to you in passing. The art of the Fedora is an entire blog in itself, but for Don’s look, choose a fur felt Fedora with a taller crown and more shallow brim (as illustrated). Ideally in a mid grey with a darker wide band to match the suit.
*Black Shoes
Black, shiny, and a square round toe. Nothing too pointy or super almond shaped for day time office wear. These are the shoes a man shines himself (or has shined if he is so lucky) and acts as an advertisement for just how well he is looked after at home. Subtle, but don’t head into the office with a scuffed pair or people will think your wife has left you!
** So now you boys have one for yourselves, keep those contest entries coming! **
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yes, my husband is lucky enough to have his shoes shined for him… that and the time he did it himself he thought it would be a good idea to polish the bottoms as well
Oh, if only men now dressed as sharply as they did then… don’t get me wrong, I love my Love’s metal look, he suits it, but there’s nothing like a well turned out suited and booted gentleman!
Ooh fantastic post! I love this style. I want to find the perfect fedora for the mister.
And I’d love to enter this competition, i’s such a great idea, but I’ve only seen two episdes of Mad Men (I’m doing it the old fashioned way, on regular telly, grr) and don’t think I have anything that’s just right :< I can’t wait to see the entries!
Marianne: Just do a Google search for ideas. I think you could pull of the secretary look really well.
Terrific post, great stuff! FYI this style of gentleman’s hat is known as a Trilby not a Fedora
[...] some days I secretly long for the prehistoric age when Don Drapers roamed the earth. When men wouldn’t leave their houses without a smart-looking hat. When women wore dresses [...]