The Tale of the Cheap Dress Shirt

While looking at my closet the other day, I wondered what my “style” really is. I found a mixture of t-shirts, dress shirts, suit jackets, sports jerseys, ties, jeans, dress pants and a few brave remnants of the late 90s I’ve never been able to bring myself to throw out. I’ll wear any of these (except the 90s refugees) on any given day and feel equally at home in any of them. Should the occasion call for it, I’m more than happy to rock the suit and tie – and sometimes, even when it doesn’t call for it. If it’s a casual day, jeans and a nice t-shirt are always an easy option. No matter where I show up, my friends and the people that know me are almost always prepared for whatever wardrobe choice I’ve taken that day.

This thought process got started the other day when I had a meeting at one of the office towers downtown. People in suits and power outfits blazed back and forth between offices and overpriced coffees. The sun reflected off of over-shined shoes and brass-cornered briefcases. In the midst of all this I parked my 20 year old sports car, slung my bag over my leather jacketed shoulder, and walked to my meeting. I made my way through the crowds and into the building my meeting was at. As I waited for the elevator, two other gentlemen came and waited beside me. They gave me a quick glance, surmised I wasn’t part of their group, and continued their conversation about nothing in particular. As I looked at them, I wondered if perhaps I was underdressed. In my head, the old Sesame Street song “One of these things is not like the other…” started playing. However, as it did, I looked at them again. The shirts were poorly cut, wrinkled, and looked like they’d skipped a wash cycle or two. Their collars were loose and the ties they wore didn’t go with the rest of what they were wearing. Generic, grey pants stood unevenly over dirty brown shoes.

My skin bristled. Not at their fashion choices (for the record, I can barely tie a tie – and don’t ask me about stripes with stripes – I have no idea) – but at their overall inauthenticity. I’d rather have shown up in shorts and sandals than be in the shoddy outfits they were in. They were dressing to a dress code, sure, but that was it. I understand not liking a dress code, I understand being a bit behind in your laundry – but if you have to do something, do it properly, yes?

I remembered my days of freelancing back in Kamloops, BC. I was fresh out of university and anxious to build my empire. My clients ranged from nightclubs to restaurants and party planners to auto body shops, clothing stores and even a tanning studio. The styles of work I did for each was vastly different; as was the way my clients thought of me. For one client, I would always show up in a freshly pressed shirt, cleanly shaven, early in the morning. For another, they knew me as the “crazy, rock’n’roll artist guy” (their words, not mine!) that had been out the night before at one of the nightclubs I worked with until all hours of the morning, no matter what day of the week it was. When I was meeting with them, I wouldn’t shave, leave my hair a bit more dishevelled (I mean hey, do artists really care?) and would put on something usually more appropriate for the club.

The thing was, I wasn’t being dishonest with any of my clients in my appearance. I knew what aspect of myself they had connected with, and if I enhanced it a little, I viewed it as salesmanship. If a client thought of me as the polite, well-dressed young man, I would be the best dressed man in Kamloops minding my Ps and Qs. If another thought me a gear head like the guys that worked in their shop, I’d make sure to talk about my cars as much as I did with friends and not clients. The point is – no matter where I was, I was genuine. I was comfortable and at ease.

It’s such a simple thing, but being okay and honest with yourself can help you face whatever difficult situation you are in. If someone isn’t being honest with how they’re presenting themselves to you, what else aren’t they being honest about? If they don’t care about how they look and how they represent their company.. well, you get it.

The elevator chimed and they both left. They turned a casual glance back at me, and I felt as if I was standing perhaps just a touch taller. Yes, I’d left my suit and tie at home, but I wasn’t the one pawing at my collar and itching out of my skin.

The doors closed again and I smiled to myself. I walked into a room full of fellow business owners who returned my smile when they saw me. I set my jacket and bag down and got compliments on my company shirt. The meeting began, and all thoughts of clothing and being genuine were cast aside. I didn’t need to think about these things, as I was where I was meant to be. My clients and colleagues had recognized me for who I was, as I had them. Business was discussed and goals were achieved.

Somewhere in a small town, and many years ago, a younger me in a jean jacket is smiling and happy.


– Jason
Founder, Ambition Branding