Lessons In Menswear From Anna Karenina

I just finished reading Tolstoy’s Anna Karenina. I enjoyed it immensely.

I have been on a kick for the past few years of reading as much classic literature as I can. It came from a realization that there were a ton of books that are constantly referenced in popular culture that I had never read. The kinds of books that everyone “knows” but few people have actually tackled.

I think the major barrier that keeps people from reading classic novels is the expectation that they will be difficult or boring. Maybe it was the translation I read, but I didn’t feel that Anna Karenina was either of those things. I never found myself skimming sections or waiting for chapters to end. I guess Tolstoy was a pretty good author.

At a hair over eight-hundred pages, it took me the better part of this year to finish. I don’t enjoy reading in little clips, so I need to set aside good chunks of time, which, we dads know, are hard to come by.

The novel takes place in 1870s Russian high society, so the descriptions of what everyone is wearing are fascinating. Everyone’s in ball gowns and military uniforms and tailcoats.

There is only one spot, though, early in the story, that clothing plays an integral role in the advancement of the plot. It is this spot where we can glean some vital lessons in menswear.

Now, I say “menswear” but the instance to which I am referring occurs between two women and what they are wearing. This will all make much more sense soon, I promise. First, let me provide a little context…

Anna is in town trying to help her brother reconcile with his wife after he just cheated on her. The betrayed wife has a younger sister, named Kitty. So, Anna and Kitty are kind of distant sisters-in-law.

Anna is married to a much older man, and they have a nine-year-old son. Kitty is eighteen-years-old and hoping to get a proposal from the wealthy, handsome Vronsky.

Both Anna and Kitty are described as beautiful, but Anna’s particularly affecting allure comes not only from her beauty, but her compassion. She is the ultimate “people person”. She is a sophisticated, confident woman. Pretty much everyone she meets loves her, Kitty included.

At the start, Kitty looks up to Anna they way a kid looks up to an established adult whom they someday wish to emulate.

Since Anna is in town, Kitty begs her to come to a ball later that night. Initially, Anna says no, since she finds balls to be boring now. But Kitty presses the issue and Anna relents.

Kitty says that Anna should wear lilac.

At the start of the ball, Kitty is feeling great about herself. She’s wearing a pink dress. She has her hair built up into an elaborate hairdo using hair extensions. She is sure that Vronsky will be impressed.

Unfortunately, for Kitty, Anna gives her a masterclass on how to dress like a grown-up.

When Kitty sees Anna she practically has a “You’ve gotta be f-ing kidding me” moment.

Anna isn’t wearing childish lilac. No, no. She’s in a low-cut, off-the-shoulder, black velvet dress. Her hair, unlike Kitty’s, is her own (no extensions) and done simply.

Her appearance is described as simple, natural, and graceful. Her mood gay and animated.

One great line states: “What she wore was never seen on her.”

Anna doesn’t need any of that silly affectation that Kitty’s using. She doesn’t need it. And she knows it. This is a grown-ass woman, not a kid. At this point in her life she knows exactly how to dress her body. Her clothes are not covering up or hiding anything. She knows what to wear to enhance her naturally beautiful appearance.

For Kitty, balls are still novel and exciting, so she gets all dolled up hoping to attract some attention. For Anna, balls are a big yawn so she throws on “what-this-old-thing?” and drops the mic like a God-damn diva.

Kitty probably took four hours to get ready. Anna? Likely twenty minutes.

And whom does Vronsky fall head over heels for? I’ll let you figure that one out for yourself.

So what does this teach us about menswear? I think first and foremost it teaches us to dress our age. Even though Anna is beautiful, she is still described as being somewhat envious of Kitty’s youth and beauty. But at the ball, Anna doesn’t try to compete with Kitty on Kitty’s level. That is, Anna doesn’t attempt to dress like an eighteen-year-old debutante because she would look silly.

Likewise for you, dress your age and don’t hide it! You will look much better in a tweed jacket and full-cut pleated trousers than in the skin-tight high-waters those twenty-somethings walk around in. I see these middle-aged style influencers on Instagram dressing like teenagers. Sure, they might get some likes on their picture, but everyone outside of that very small community thinks they look ridiculous.

Grey in the hair or beard? Embrace it!

Dress the way a grown man should and show the kids how it’s done.

Now, it’s never specifically stated whether or not Anna purposefully dialed up the hotness in order to outshine Kitty. It isn’t until later in the book that Anna weaponizes her beauty and charm during an impromptu meeting with Kitty’s future husband, Levin. Even the morally rock-solid Levin leaves that meeting partially under Anna’s spell.

Secondly, yes, Anna looks great in her booby, black dress. But it’s her ease and confidence that draws Vronsky to her like a tractor beam. When the pair is dancing, Kitty, having cruelly been left out in the cold, watches them from afar. She can’t hear what they’re saying, but can plainly see their faces. She sees how Anna responds to everything Vronsky says with smiles and flashing eyes. Anna’s actively listening and making Vronsky feel important. All this reduces the normally self-assured playboy into a puddle of mush. It takes all of twelve seconds for Anna to make Vronsky fall in love with her.

Now, in this instance, Kitty describes Anna’s wiles as “terrible and cruel in her enchantment” and “alien” and “demonic”. This is because she is pissed about losing Vronsky. But no one else feels that way about Anna (save her jilted husband). Even though Anna cheats on her husband and abandons her child, everyone who knows her still holds her in pretty high regard.

Let’s be clear: I am not advising you to weaponize your natural magnetism to make people fall in love with you. What Anna is showing is that without her sparkling personality and her ability to TALK to people and make them feel listened to and cared about, she would be just another pretty girl.

It’s not Anna’s clothes that are doing the talking. Again, “what she wore was never seen on her”. Follow Anna’s lead. You can be very simply dressed and still look like a million bucks if your personality is on point. That means: treat everyone with respect and listen intently when people talk to you. People will remember YOU as being attractive, not “oh, he was dressed nicely”.

Anna’s innate personal magnetism reminds me of the husband of an old friend of my mother’s. Dave was a high-level businessman and because he and his wife lived most of their adult life in Europe, I only ever saw them on occasion.

At one point they were staying in NYC for a few days and invited my family to dinner at their hotel. I was maybe twelve-years-old but I remember noticing how everyone was drawn to him. More specifically, I noticed how he treated everyone which, in turn, drew them to him and made them love him.

He was a tall man and had a bit of a laconic way of movement. He never seemed agitated or nervous. He was always deliberate with his motions.

The moment that most stands out in my memory was when we all took our seats at a large table. Dave was, naturally, at the head. The young server approached and stood next to him. Dave then slowly turned to the server and gave him a warm, double-handed handshake.

That was it. That’s my memory. But it sticks out so vividly in my mind as an example of someone whom people just wanted to be around. Little moments of connection or tenderness or humanity. Honestly, have you ever shaken the hand of your server at a restaurant?

Was Dave well-dressed? You better believe it. But I don’t really remember exactly.

Like Anna, what he wore was never seen on him.

There are so many interpretations of what it means to be “well-dressed” or “stylish”. My advice to you is to be like Anna: dress your age and let your personality do the rest.