What I Learned From the “Check Your Head” Shirt



This damn t-shirt: the end of innocence. Circa 1987.

In 7th grade, fitting in was pretty much the entire game. It was 1987; despite the fact that it was 20 below on the shores of Lake Michigan, everyone dressed like they were about to go surfing. As for me, I wore whatever corduroy slacks my mother dropped on me. Then, one day, every single kid in my grade came to school wearing a t-shirt: an airplane crashing vertically into the ground.

To my eyes, this shirt was ugly (which it is, I guess) and everyone wearing it was an idiot (which they were, given that this was 7th grade). Plus: Licensed to Ill? Bad grammar.



I never fit in which trendy people like these. Perhaps to my credit.

I claimed not to want to fit in, and to some degree, I paid the price: I ate lunch with two other non-cool kids in the library. Instead of jockeying for the best seat in the cafeteria, we talked about the books we would one day write. Instead of talking about “who liked who,” we discussed our favorite sci-fi movies with the librarians (remarkably funky people for Mequon, Wisconsin).


We were happy not to fit it. But we weren’t exactly comfortable with who we were, either. Dropping out wasn’t the solution.


sheep.jpgAs an adult, I’ve made peace with License to Ill (it’s an AWESOME album), and with trends of all sorts. It helps that, as I went through my twenties and thirties, fitting in via the fad du jour, whatever form it took, became the province of people I don’t have to trouble myself with.

For the rest of us, the important “fitting in” is not about where you are or what you wear or what you listen to, it’s about fitting into your own skin. We admire (and strive to be) confident in who we are. We admire people who are comfortable with themselves, comfortable with their surroundings. And the people we really admire are the ones who make everyone else feel comfortable, as well.

And by the way, if this isn’t the way your world works, consider moving to a new world.

on point.jpgBehind the scenes, fitting in with your world is more than putting on a confident face and striding into a room like you own the place. It’s also about how you present yourself. How you “read.” And if you don’t think that’s true, consider the reoccurring dream where you’re naked in front of an audience. Oh, you know that dream? Exactly: everyone feels, to some degree, unclothed – vulnerable – with our doubts and anxieties. We do our best to dress ourselves, metaphorically, with confidence. And we can wear actual clothes, hopefully with confidence, every day.

When your clothes fit, we call it “on point.” When they fit together, we call it a great “out-fit.” It’s like, literally, you fit to the outside eye. The effect is pleasing and it ascribes characteristics to the wearer: you’re put together You fit.

And then there’s fitting the scenario: the perfect suit to an interview, the perfect blazer for a first date, the perfect outfit to a bar-b-q. You are in harmony with your surroundings.


Then, there are the seasons. To some, it’s always khakis and button-shirt season. But seasons give us an opportunity to stand out for fitting in – not with fashion trends, but with the world around us.

Below, I show how dressing to fit in with winter includes colors, materials, and layers.



Outfit One: #Tweed is the Tweet

To begin with, this outfit features a few “all-year” items: Levi’s (more than “all year” – they’re like “every damn day”), Clark’s Original Desert Boots, and a denim jacket.

Then, two “signifiers” indicate: “Yes, I know very well what season it is.”

  1. The tie.
  2. The vest.

Both of them are made of heavy tweed, a heavy material who comes out to play during the cold months. Obviously, the tweed tie isn’t going to keep me warm when San Francisco fog coats the city in grey brrr, but it sends the message: it’s winter, and I’m cool with that.

 Outfit Two: Black Turtle Necks, Beyond Steve Jobssherpherdsuit

Here, Gabi and I are attending a party in some swanky loft. It was a suit-worthy affair – but also, after work during the coldest month of the year. No mere “dapper suit” would flip its finger to the 40-degrees-and-raining-like-hell situation outside.

This suit, to begin with, is made of a thick, shepherds check – in black and white. Paired with a black turtleneck, it’s heavy and stark (like winter) but playful, as well.

Your winter fancy-pants should be flannel, wool, and other heavier weaves. Again, no one will haul you to fashion-jail if you’re wearing khakis, but why not radiate cozy-winteriness?

Outfit 3: Ski-Lodge on the Rangewooltieandsweater

Obviously, when temperatures dip, it’s a good time to bust out the heavy sweaters. But if you wanna get dappered up, and you pair your heavy, snuggly sweater with a bar-mitzvah tie, you’re going to undo the “fitting-in-with-the-seasons” thing you’ve been working so hard on.

Fortunately, there’s knit ties from The Tie Bar.  These things are so affordable, and so beautiful, you’ll do one of those guilty “looking both ways to see if you’re in trouble” things before you whip out your credit card.

When it arrives, pair it with a cozy sweater and a denim shirt. Don’t be surprised if someone asks you to join them on a one-horse-open-sleigh.


Outfit 4: Pulling the Wool herringbone.JPG

Our last outfit demonstrates a simple principle: texture+texture=winter.

Warm weather tends to feature bolder, stripier, polka-dottier patterns. Cold weather, on the other hand, is all about texture – meaning, you don’t see it until you look closely.

From afar (like, normal, non-creepy distance), it gives the impression of thickness. And thickness fits in, beautifully, in winter.

Combine a textured tie, jacket, and pants, and you look cozy-warm and on-point.


Try some of the tricks above, and experiment with the feeling of fitting-in that comes through embracing the seasons.



Ankle Jewelry

sox4 What do you call a thin band of color that you wear around your neck?

  • A necklace.

What do you call a thin band of color that you wear around your wrist?

  • A bracelet.

What do you call a thin band of color that you wear around your finger?

  • A ring.

What do you call a thin band of color that you wear around your ankles?

  • Socks.

 Socks are ankle jewelry.

Many men are hesitant to wear jewelry because, well, whatever. No need to go there. In any case, colorful-but-classy socks can be a styley substitution for  bracelets, necklaces, and rings.

Here are some rules of “thumb-toe” for socks.

Crank it up, but keep it under control. Yes,  there is a bit of a “Happy Sock” thing going on out there, you don’t need goldfish, moons, or MC Escher on your socks.

You do not want to be "the guy with the socks," so avoid Bat-Man, the Benjamins, and over-the-top colors.

You do not want to be “the guy with the socks,” so avoid Bat-Man, the Benjamins, and over-the-top colors.

Determine what color-palette you are wearing.

A) blue, red, black, white, and grey B) purple and grey C) Green, tan, brown, orange, and other autumn colors

Stick With Cotton

It breathes and the colors pop. Avoid polyester-blend “dress socks” – the thin, wrinkly things sold at department stores and menswear stores.

Now, pick your pattern:



Stripes: go with one color, and wear with grey, blue, black, or red pants.

Keep the stripes simple. We’re going for a bit of pizzazz, not “hey, look at my socks.”

steven allen

Polka-dots: stick to one color.

Polka Dots

Only if they’re ONE color.

Argyle is Awesome


Argyle: Wear with wingtip shoes.

Try purple and grey with a grey suit or red and blue for…anything.



Gingham: Great with jeans, grey dress pants, or red/blue chinos (casual pants)!


Will net you compliments. Stick to blue, red, brown and purple.

Now that you’re a sock-maven


Cool shoes. Perfect cuff. Now, swap in some color. (Picture from

Consider getting your pants tailored so there is no “break” – (“break” is the word for what normal people call the sag-fold that forms under your knee or near your cuff when your cuff hits your shoe).

Have the tailor hem the pants so just a sliver of sock peeks out. Not only does this give you a streamlined, clean shape, but also, it shows your ankle-jewelry. I’ve learned from experience that socks are an amazing “just because” gift. They’re fun and don’t cost much.

Next time you’re being dragged around a mall, try buying your girl-friend a pair of “just because”  earrings; if you’re lucky, she may surprise you with a little “bling” of your own.

Some sock brands to check out:

Banana Republic: Get some nice stripeys.

Richer / Poorer: Small company, great designs.

Lifetime Collective: Never heard of them? Fix that.

J.Crew: Yes, you’ve heard of them. But did you know they can be your sock purveyors?

Happy Socks: Now that I’ve criticized them…if you keep the colors and patterns under control, they can be kind of amazing.

Quiz time: which of these Happy Socks are a little too much of a good thing?

Quiz time: which of these Happy Socks are a little too much of a good thing?