This is a guest article from Derek John.


Were you a Mad Men fan?

It’s pretty obvious, but much has changed since the 1960s. The way our suits are constructed, how we wear our hair, and many other fashion ideals. One thing that remains today is the idea that “Classic never dies.”

The widespread popularity of AMC’s Mad Men has redefined what it means to be dapper.

The show has not only brought back to life the value of a great suit, but also influenced a new interest in the art of being a gentleman.

What is the art of being a gentleman? It’s simplicity. It’s keeping neat, trim, clean in appearance, and handling yourself with good conduct.

Here are seven simple ways to be as dapper a gent as the characters of Mad Men.

1. Redefine your casual wear

7 Ways To Look Dapper Than Mad Men

In Mad Men, the dress code is slightly different than modern day. In the 60s, if you were going out in public, you’d be dressed to the nth degree.

Yoga pants weren’t considered casual. Interestingly, what would be considered casual today was only to be worn around the house back then.

Push your idea of casual further than shorts and a t-shirt. You can make your outfits more exciting by utilizing staples like a sports coat, crew or V-neck sweaters, and a good pair of chinos.

Editor’s note: On Effortless Gent, great casual options are part of a Lean Wardrobe. Learn how to easily build one here.

2. Understand the power of a tailored suit

7 Ways To Look Dapper Than Mad Men

Like I said before, the way our suits are constructed these days is different. Don’t worry; you don’t need to go out and by suits with higher waistbands and shorter jackets.

Whether you’re suiting up once or every day of the week, it’s important to have one well-fitted suit in your wardrobe.

You should invest in a grey or navy suit. These colors are the most versatile and are widely accepted business attire.

Complete that with a nice white dress shirt and a tie and all of a sudden you’re channeling the Creative Director of Manhattan advertising firm, Sterling Cooper.

3. Get a sharp haircut

7 Ways To Look Dapper Than Mad Men

Find a good hair stylist and get yourself a sharp haircut. You can probably walk into any barbershop and ask for the Don Draper, and they’ll know exactly what you’re asking for: short on the sides and back, longer on top.

This is a very classic haircut it’s back in style and here to stay. It’s a clean, versatile look that can be styled via the Don Draper side part or slicked straight back. Either way this is a trademark of dapper men.

If you’d prefer a more modern look, ask your stylist for a “disconnected undercut“. This is essentially the same cut, but the sides and back are clearly cut shorter than the top, with less blending between the two areas.

4. No empty pockets

7 Ways To Look Dapper Than Mad Men

If you pay attention, you’ll notice Don Draper and his associates are rarely without a pocket square. Each of them subscribing to a different fold, color, and style.

Don prefers the horizontal fold. Ron is partial to the Three Point Fold, and Bert Cooper (not pictured) likes the Four Corners Up.

It’s second nature to these gentlemen. You wouldn’t suit up without your pocket square like you wouldn’t leave the house without your phone. You’re naked without it.

You can find out how to wear your pocket squares here.

5. Don’t neglect your footwear

7 Ways To Look Dapper Than Mad Men

While you might not be as obsessed with shoes as I am, you’ll need one or two great pairs of dress shoes.

The boys up top are wearing oxfords or monk straps. Both shoes can be worn formally or casually, and can be found in a variety of different styles.

If you haven’t already, I would invest in black or brown oxford shoes (Editor’s note: …in addition to the four other pairs of shoes you should own.) If your lifestyle calls for formal attire, go with black. Is your wardrobe more business casual? You’ll be better off with brown.

6. Have your “usual”

7 Ways To Look Dapper Than Mad Men

Never sure what to order at the bar? Stuck staring at the menu, or simply defaulting to beer?

It’s good to have your set of usuals; the same 2-3 cocktails you can order no matter the bar you’re in. Typically, these are classic cocktails. You can fish around for ideas, or simply start with the Old Fashioned.

The Old Fashioned is a staple amongst Don Draper, the rest of the cast, and dapper men alike. It’s my personal favorite!

It’s a classy cocktail that’s made with bitters, sugar, whiskey, and a citrus rind. Throw in a few ice cubes and you have yourself a very masculine drink that is both timeless and refreshing.

7. Stay in shape

7 Ways To Look Dapper Than Mad Men

I’m not talking about going out and adopting a whole new exercise routine, just be slightly more active than you are right now. Back in Mad Men times, people were much more active and obesity wasn’t as prevalent as it is today, which probably also has a lot to do with diet and the types of food that were available.

The point is, if you’re behind a desk most of the day, then get out and get social. Do things that are fun. Move.

Go for a walk.

Go dancing.

Walk to work.

Ride a bike.

If you like structure, find a challenging beginner workout you can stick to.

These little things add up over the course of the day.

Are you a dapper Man?

What are some ways you stay dapper? Let us know in the comments below.


Photos courtesy of AMC

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13 Responses

  1. Donnyboy on

    I was a kid in the 60’s and loved to watch my Father suit-up for work, it definitely shaped the way I dress and carry myself. I am also a fan of the looks, styles, architecture, etc of the era, but to call the characters in the show “gentleman”?!? I LOVE them all – Roger & Don in particular -but they were anything but!

  2. melmoth on

    I like number one because it’s often overlooked. Of course if you’re going to commit to suits and dressing well then that’s a whole project/hobby to focus on. But then it’s easy to slob out on a casual day and I think that’s a mistake.

    “Casual” is a whole new chance to put together good looks. Chinos, loafers, a wider range of color in your shirts. A wider range of watches and watch straps.

    Check out how abysmal this set of BILLIONAIRES looks at a casual morning meeting at their annual Sun Valley gathering. Chinos, loafers, leather belt and a decent tailored shirt? Nah, can’t be bothered. Unreal and actually quite shameful, imo. About one in five seem to be adults, like Jerry Yang, Dick Costolo and Robert Marcus. The rest are eighth graders. I know, “Irony, eccentric geniuses blah, blah.” Put on a damn shirt. Looks like 4 out of 5 are in their running shoes. You going running guys? Going for a run then right? Certainly you must be because you have running shoes on.

  3. Sean on

    Dapper yes, but the characters on the show are anything but gentlemen. Cheating on their wives with the secretaries, lying about military service, etc. I love the show and the style but consider them gentlemen, not even close.

  4. John Doe on

    I stay dapper with a good, baby-butt smooth classic wet shave. Straight edge, build your own lathers instead of using aerosol canned shaving cream.

  5. Gazman on

    Thought Mad Men was very true to the style of the era in which it is set. But looking at the pic in point 5, there’s no way men of the day wore their pants with no break.