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  • Writer's pictureEvan Wolkenstein

What Tailoring Teaches Us About Growing Up: New Year’s Resolution — 30 Days of Writing. Episod

This is day 5 of a New Years Resolution.


Until I was 35, I’d never taken anything to a tailor.

Well, that’s not exactly true – I got a vintage suit when I was in college, but the pants draped down over my shoes, and the jacket was too big. But my parents orchestrated (and paid for) the whole thing, so I don’t feel like that counts.

Behold: the majestic shirt of non-fittage. Circa 2008.

Behold: the majestic shirt of non-fittage. Circa 2008.

But when I was thirty five, I got this brand new, awesome — (pauses to consider name of color) — burnt-umber colored shirt. And while I loved it on the hanger, when I put it on, I didn’t feel “classy” or “dapper” or even particularly grown-up. In fact, I felt like I used to when I was 14, and would borrow my dad’s shirt, tie, and jacket for Rosh Hashana services.

At first, I chalked this feeling off to a delinquent Saturn Return.

But I started to notice: in rooms full of well-dressed adults, say: a gala banquet — it didn’t matter what color my shirt was, or how cool my shoes were, or how well I matched my tie to my shirt, I seriously never felt like I belonged. 

One day at work, I asked a very dapper friend if he could direct me to the store that sells the shirts that fit. His response?

Do what grown-ups do, and go get your shirt tailored.


Ok, so he didn’t mean the burnt-umber atrocity, per se. That thing needed to be phased out, stat.

But I did pick out a few respectable shirts and I brought them to a place that Yelp reassured me wouldn’t ruin them, and one week later, I put on this newly tailored white shirt. Nothing special about the shirt. White. Buttons. But I noticed something profound.

It fit. I fit. I fit myself, if that makes any sense. With a decent tie and shoes, I’d be comfortable in any board-room (or bar-room) in this glorious land.

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, help you feel united with yourself, and connected to the world.

Weird, but true.


Warning: if the shoulder seams don't hit right at the shoulderbone, it's hopeless. Give the shirt to someone who needs it more than you do.

Warning: if the shoulder seams don’t hit right at the shoulderbone, it’s hopeless. Give it to someone who needs it more than you do.

FAQ about Tailoring Your Shirt

Q: What will this so-called tailor do to my beautiful shirt?

A:  Shorten the sleeves (even a great tailor cannot lengthen sleeves), de-blousify the upper arms (my neologism, there), and get rid of the tenting, billowing, and poofing in the back. If you don’t know what I’m talking about, you’re a lucky guy who fits stuff right off the rack, and no offense, this article isn’t for you.

Q: What will it cost to turn a shirt that doesn’t fit into a miracle of Joie de Vivre?

A: 20-40 bucks.

Q: What? The whole shirt cost me thirty bucks!

A: Ok, so here’s the deal. If the shirt fits right off the rack, great: Bob’s Your Uncle. But if it doesn’t fit, you need to do a little calculating. Is the $25 shirt from H&M worth tailoring? Only if you can’t stand how it fits, but you couldn’t live without it. You know, like the U2 song.

So, maybe you have a nice Brooks Brothers or J.Crew shirt but the fit is a little off. Better to spend $40 on a perfect fit, or go out and find something else that fits better off the rack? Do the math. What’s your time worth?

Q: So when I buy a shirt, I might want to calculate the cost of tailoring into the cost of the shirt? Seriously?

A: You want to feel that one-with-everything feeling or not?

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