I turned on the light to my closet and walked in. It was 7:30 on the morning of a client meeting and, as usual, I needed a dress shirt. I don't have a wide range of dress shirts since I can get away with casual shirts at work, and so my selection is somewhat limited. But on looking at my options, I was disappointed. All of them fit well except in the arms which, as usual, were too long. I chose a solid blue shirt, conservative but business-friendly, and went on my way.


It's no secret that I'm short even though I look tall on Twitter. 5'6" is my height but, honestly, that's when I'm wearing my Chippewa boots in the fall or winter. I'm 5'5 1/2" to be precise. And, due in part to my short stature, I also have relatively short arms and legs.

When I was younger, I didn't quite understand why my school uniform pants always needed to be hemmed. And as I progressed into men's sizing, I didn't quite get why a 30" inseam on pants meant that I was still dragging a few inches of denim on the floor. But there I was. Once I entered the business world, though, I knew I had to get my clothes tailored to some extent. That meant dress pants for sure (although there was a time where I tried to get away with cuffing – a bad idea) and that was also true for my lone suit and lone blazer.


The following week, another client meeting and another round of frustration with my dress shirts. I chose a white shirt, somewhat formal but not too too formal, and finished getting dressed. I had bought that shirt last year during a dress shirt replenish, but never took the time to get it tailored. I wore the shirt but felt really bad about it all day even though it was under a blazer – it circulated in my head as one of those things that you notice immediately but almost no one else would. (“Can they... tell? Do they think I look silly?”) I'm sure it manifest itself in my stance and confidence that day.

Not long after that, I found myself at Nordstrom Rack trying on new dress shirts. I found one that fit really, really well. It was a reasonable $35. I looked at my reflection in the dressing room mirror and nearly bought it. It was a good shirt.

But here's the thing: the shirt in my closet at home was also a good shirt. Its sleeves were just long and a little big, that's all. (If I ever took up weightlifting, and somehow only grew larger muscles in my arms, this shirt would have me covered.) But it was nothing a tailor couldn't fix. I left the store empty-handed, and called the tailor just down the street from work. $14 to shorten sleeves and a week turnaround. No worse than buying a new shirt online, say, and waiting for shipping. I dropped by the tailor and tried on the shirt.

“How short do you want the sleeves?” he asked. Ooooh, the voice in my head thought, he totally can't tell.

I pulled up the sleeves maybe 1/2" or so and said, “That's it. Not much.” He marked the sleeves. I paid my $14, changed back into my other shirt for the day, and was off.


All of this made me think about how willing I was to purchase a brand new 100% fine shirt which, I might add, would have likely also needed some tailoring. I was almost willing to spend about $50 for a new shirt that day at the store, versus plunking down less than $20 to take care of the shirt I already had.

For quite some time I just thought that clothes were supposed to fit off the rack, and if there was something wrong with the sleeve length or what-have-you, too bad for you. My stance on this has changed. Yes, it totally sucks that I have to tack on $20 to just about any pair of pants I buy unless I happen to find one in a short length (which, thankfully, happens.) And no, I don't plan on getting my entire wardrobe tailored.

But there's something to be said here about the idea of reinvesting in what I already have versus throwing it out and getting something new. New is appealing. New is flashy. New is... new. It sounds good to have new stuff. Look! I got a new shirt! I got a new phone! I got a new pair of pants!


I picked up my shirt a week later at the tailor. I was genuinely happy as I got the plastic-wrapped shirt off of the rack and said thanks to the tailor. I got it home that evening, put it on and...

The sleeves were too short.

They looked ridiculous. It appeared as if my arms had grown out of my shirt, leaving no fabric behind. Worse, the arms were now so short that the shirt pulled across the chest and back. The tailor had ruined my perfectly good shirt. And this, unlike the sleeves being too long, was something others would absolutely notice.

In the end, I made the best decision: to stick with something I had, but update it to reflect how I actually was in that moment. Unfortunately, the too-short-sleeve-shirt was a byproduct of a tailor who made a mistake. While I might go to him again, I am worried to take another shirt there. Pants, no problem. But now I know that this tailor isn't where I'll take my shirts. Lesson learned.


There is value in sticking with something that is familiar and seeing it through to whatever you need now. It can be tough sometimes. It may cost money. It may not be possible today. It may be possible tomorrow. It might hurt, because that shiny new thing is shiny and new. But it may, in the end, be the totally right decision... even if there are mistakes along the way.


This is based on a piece I wrote for The Weekly, my email newsletter.