In many ways in life, I was a late bloomer.

I didn’t feel at ease, socially, until well into college. I started dating in my 20s. And I started watching Mad Men when the rest of the world was on season four.

At that time, I had no place in my life for a TV series, but other things in my life were in already flux. I was in a new relationship. I was approaching the end of my 30s. I was beginning to reinvent my own personal style. And that was the bait and switch.

I was told that the show featured great style, and I was hungry for that, curious what I would get out of it. I had no idea, seven seasons later, how much I would give to it. And I’m not just talking about how much I would invest in the characters, or how many meals would be spent teasing apart the show’s subplots and themes. I’m talking about how I would see and understand my own growth, and the development of my own, personal style, in a kind of partnership with the show.

Took a while to get to this look. Think I’ll keep it for a while.

1. Excellence in style is not about what you wear, it’s about how you wear it.

Naturally, this list must begin with Don, and the most notable thing about what Don wears is how little there is to say about it.

We’re struck by the stack of clean, pressed shirts in his desk drawer. We’re enamoured with the grey suit, the striped tie, the plaid short-sleeve shirts, but in all, what he wears is noteworthy because of the understated nonchalance in a world where the norm for style has become increasingly grabby, self-conscious, ostentatious.

Style, in that sense, is about being at home in space and place. Myself, I lived in 7 cities before the age of 40; I meandered not only geographically, but also academically, religiously, in complex life decisions and in style. All the while, however, I have tried to live with my actions and my identity in alignment – in flux as they may have been. Only now, however, has my sartorial style “become at home.” And while learning to understand Don is learning to understand how lost he is, it’s also to appreciate the journey to be “at home,” where outfit and outlook are in alignment.

That person, no matter what he wears, is in style.

2. Fit is a thousand times more important than fashion

60s. Got it.

70s. Don’t got it.

As the style of the mid 60s passes and the 70s approach, a strange sacrifice takes place: along with the rise of radical individuality, the invention of global pop-culture and the celebration of personal expression comes the introduction of a generation-long trend in style. As the show closes, proportion and propriety go out the window as fashion conventions (not to mention patterns, colors, and fabrics) give way to the free-for-all of 70s fashion.

The 60s in their glory, outfits are on-point, and Ginzberg is kooky.

The 60s wane, sleeves get baggy and Ginzberg goes insane.

On the one hand, I’ve never been one to denigrate the freedom of expression – and more importantly, there was a lot, a lot about 50s and 60s American life that needed to be shed to pave the way for progress. Societal expectations, rigid class, race and gender expectations soften, and the promise of freedom is in the air. On the other hand, and speaking plainly, much of the next phase of style is about statement rather than aesthetic, and the price to pay is that everyone looks plain awful.

In my own exploration of style, I have often found that minimal, understated, and well-tailored rarely goes wrong. And conversely, yearbooks and wedding albums from the 70s and on are full of fashion experiments that might have looked good on a catalog or runway, and bad on everyone else.

And rarely is the issue about pattern or color – as these things fall in and out of favor. But rather, it’s about whether the clothes fit the wearer, or does the wearer wear fit the clothes? Tailored was out. Mass produced was in. Clothes got cheaper, closet sizes expanded, and from a style-perspective, everyone paid the price.

In my own life, as I began to explore the world of style, I bought (and donated) a lot of clothes that made a variety of statements. It took a while to discover what Mad Men’s early seasons knew, and which won every budding sartorialist’s heart: a great fitting suit, a properly tailored shirt, a slender tie, and a clean haircut looks great on any man.

3. There’s a difference between keeping up with the times and having no core-principles

Look at Harry, for example.

Prompting the next question, which Harry?

Every season, he sheds his previous attire and becomes the poster-man-child of the new look. That said, his character is in stark contrast with Stan.

Stan, too, transforms, from on-point, polo-with-blazer, womanizing yuppie of the early seasons to the scruffy, bearded post-hippie who wins Peggy’s heart.

But whereas Stan evolves as a character, being one of few characters to reflect on who he used to be, and who he is now, Harry devolves. He is on-point as he jumps about the TV bandwagon, as he sidles up to the power of computers in the workplace, but he has no honor, no loyalty, culminating in his cringeworthy amorous advances on Joan in season seven.

Evolution is beautiful.

Stan becomes only more trustworthy, more loyal, more sensitive and more honest. His style is a reflection of who he is. As homage to his character, his outfits somehow work, and he is somewhat immune to some of absurdity of the era’s style.

Harry is last shown in a coat we have seen in a hundred thrift-shops, whining about his lunch plans, shoving a cookie in his mouth. Hardly a memorable exit. Stan exits, embraced, loving and in love.

In that sense each shows the light and dark side of style. It can be fickle, a costume, a mask, a way to express power or amass social credit. Or it can be a sincere representation of where someone is, and even an aspiration of where they hope to go.

I hope, dearly, that I am more like Stan.

4. When life takes out an eye, slip on a patch and soldier on

Life kicking Kenny’s ass.

Kenny kicks back.

Kenny could be a tragic character because we know he wants to be a writer and we believe he could do it. However, he is caught up in the corporate world and not only is it consuming him, it takes his eye; he loses it in an account-courting hunting excursion. After losing his job, however, he takes an entirely different path, however, and never looks back. So to speak.

He goes from tragic character to master of his own fate, no longer playing hands but dealing them to others.

We have all picked up our scars in life. Some are visible, many are not. And I am deeply sympathetic to the ways that life can drag people down.

That said, there is something inspiring about Kenny who continues forward, in essence embodying Churchill’s line: success consists of going from failure to failure with no loss of enthusiasm.

By all means, after loss, we should take time to grieve and mend. And then we should kick ass.

5. Style is in the office, on vacation, mowing the lawn, at a new-age retreat center, and when alone, drunk in a motel.

I don’t recommend getting drunk, alone in a motel. I don’t recommend making any of the deplorable choices Don makes. One does not have to act like Don, however, to learn from him.

Don teaches us that all things must be done with dignity, and dignity is very closely related to style.

In that sense, there is the dignity of a fresh, white shirt after a rough night (whether that rough night involves shady hotel-room or a baby that won’t go back to sleep). There is the dignity of a fresh, well fitting polo shirt while on vacation (whether that vacation involves running away from your crumbling inner world or a weekend in Santa Barbara with your girlfriend). There is the dignity of a short sleeve, button-up shirt when you’re relaxing at home (whether you’re in the garage, opening a can of beer with a metal “churchkey,” or sipping kombucha while trying to figure out what’s wrong with your wifi router).

Even in my worst hours, I don’t want to act like Don, but perhaps I’ve learned something from him about how to hold up my head; perhaps I’ve found some value in his proclamation: sometimes, all I need is “a shower and a shave.”