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  • Writer's pictureEvan Wolkenstein

Turning 41 and the Aftermath: 14 Days of Reflection — Episode 5. How do you know when the suit

My colleague, Dean, is a dapper dresser.

He’s pretty much a sage in any topic of conversation: how to handle criticism, how to shake off a bad day, how to turn 60 without losing your marbles.

So when Dean asked what I thought of his new, made-to-order suit, well, I was honored.

This lead to a whole conversation about fit; how do you know when you’ve achieved a perfect fit?


Humbly, I offer my thoughts.

1. When it fits, you know.

We spend a lot of time in life toiling over choices. Most of my best decisions in life were not so much something I “decided” as “came to recognize.”

In a shop, looking in the mirror, with a proper-fitting shirt, a great color or pattern, some styley, new kicks, you’ll say: whoa. There it is.

And guess what? That’s it.

2. You get compliments – on the right thing and on the wrong things, too.

Don’t embark on any endeavor with compliments in mind.

On the other hand, when you’re really nailing it, people can’t help themselves. You’ll get compliments on what you’re wearing, sure, but also, people will compliment your new haircut which you got five weeks ago, your new glasses which you’ve had for a year.

What people are picking up on is not your clothes. Rather, they can feel your confidence.

3. Your well-fitting-whatever will live on top of your pile (or at the front of the closet) because you can’t get enough.

Choose your outfits like you should choose your relationships. What sort of shirt/relationship do you want to be with? Something that pushes you out of your comfort zone but leaves you craving the “real you?” Something that is steady and constant – but a but predictable. Maybe even boring?

How about something that you’re just excited to put on. And when you say goodbye, it’s for a short while, only?

That’s a good fit.

4. It brings you joy.

To be honest, I’m a pretty spiritual guy, and I connect very much to religion, ritual, and all the spiritual stuff in the old books with the yellow pages. 

That said, I know that real joy comes from simple things. Good food. Beer. Music. Hiking. Art. And spending time with someone you love.

If you find a great outfit, it might bring you some joy. Don’t deny it. Embrace it.

It’s a tiny taste of the larger joys that life has to offer, but hey – life is tough. Snatch your joy wherever and however you can.

5. It connects you to others

My friend Luke, who has a Ph.D. and a way with words, once described his feelings about moving away from the community he’d grown close to for several years, and did this by referring to his basketball shoes: “These shoes fit so well, I don’t even feel them. In fact, it’s hard to tell where my foot ends and the world begins. That’s how I feel about you all.”

Yes, indeed. Well fitting clothes, like a well-fitting community, like a great relationship, help you feel united with yourself and connected to the world.

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