Mark Cuban posted a funny rant against wearing suits, and it got me thinking about one of the biggest dilemmas I’ve faced as a small business owner: what should I wear when I meet new clients?
In high school I was notorious for my lack of style. Near the end of my senior year, one of my close friends who had known me since middle school finally broke down and yelled at me, “why don’t you ever wear anything but jeans and a white t-shirt?” I took her criticism to heart and added one green t-shirt and one blue t-shirt to my wardrobe.
It was sometime after my entry into the tech workforce, where khakis and polos were the staple, that I started longing to work in a bank or law firm where suits were the norm. I have no idea why. Maybe something had been repressed all those years when I was the guy known for barefoot coding. Or maybe it was seeing those fashion spreads in Esquire of rural farmers pitching hay in $5,000 designer suits that left me feeling a bit inadequate.
At my last job I tried wearing a tie every day, but it just got to be too difficult to explain to everybody I saw that I wasn’t interviewing for another job, going to a funeral, or trying to kiss up to the suits upstairs. Therefore my foray into formal attire in the workplace was promptly laughed back into submission.
At least it wasn’t as bad as my brother’s experience at Procter & Gamble, where his boss finally took him aside and told him bluntly to stop coming to work in a tie.
When I started my own company I wondered, do I wear a suit to work now? Isn’t it the norm for businessmen to wear suits all the time? After all, the suit is back in style. Sure, maybe I’d take off my jacket and roll up my sleeves when I’d sit down at the keyboard, but what do I wear when I meet clients?
Maybe it’s that I haven’t had any clients that are bankers or lawyers, but I haven’t had a meeting yet where someone at the other end of the table was wearing a suit (besides my insurance representative). In fact, I struggle to remember the last time I met with someone who was wearing a tie.
I even received an email from the owner of a company where I was going for a meeting:
We are very casual at [company] - I am in shorts and flip flops. A rare day today in that I have on a shirt with buttons. Please come as comfortable as you want.
It’s probably all for the better. I couldn’t really see myself working in such a non-formal setting while wearing slacks and dress shoes. And I’ve rediscovered the joy of barefoot coding. My desire to wear suits at work has been suppressed again … for now.
5 responses so far ↓
1 Doug Karr // Jan 18, 2007 at 1:55 pm
I wear jeans most of the time with my job. However, if it’s a new client or the client dresses well, then I dress well. Why?because it looks like you’re trying!
It’s easy to never wear a suit when you’re a kajillionaire. I would never wear them either. Notice Mark even admits to wearing them earlier in his career. Unfortunately, he makes no connection between wearing them and where he is now. I’m sure of one thing… it did not hurt.
Doug
2 ChrisP // Jan 19, 2007 at 4:00 am
I was chastised for wearing a tie too! I only wore it once though…
I saw that same article and thought the same thing. I think suits are cool. I think dressing nice improves the environment. It’s similar to Broken Windows Theory. When you show you don’t care, then others start to act the same way. Dressing like a slob can do that. Of course you don’t have to wear a suite or even khakis to look sharp. These days I feel like I have to dress “down” for work, which is very odd..
I say wear what you want. You’re going to get in trouble either way. Someone is either going to not like your tie, not like your jeans, or think you’re just trying to blend in with your khakis. If you get a forewarning of what the environment is like then just adapt as needed.
The thing that really annoys me about casual wear is when I take my wife out for a special dinner at a “fancy restaurant” and everyone (including the staff) are in jeans and basketball shoes. Some of us only get to do that so often and like to make it a special occasion…
3 Ian // Jan 19, 2007 at 9:56 am
It’s nice to dress up once in awhile. But we all know that the strain of having to do it every day would suck.
Recently I went to a professional luncheon. I dressed in jeans and a button down, long sleeved shirt. Unfortunately I was the only one there not wearing a suit- I felt horribly out of place. The decision I made when I left wasbased on the topic, I figures that it would be all programmers, so I dressed the part. Boy was I wrong!
My normal attire is no pants till 3pm.
4 ade // Jan 19, 2007 at 10:57 am
Doug -
I definitely agree with your post re: wearing a suit to an interview. Maybe it was just because it was during my “I want to dress up” phase, but I had a guy show up for an interview once and I noticed it really hurt my perception of him. It was because it didn’t seem like he was trying. I don’t remember exactly what he was wearing, but I want to say it was an untucked shirt and some corduroys.
Chris -
Excellent point tying it to the Broken Windows Theory. I think you hit the nail on the head.
5 ade // Jan 19, 2007 at 11:11 am
Ian -
That’s hilarious. I’ve been in similar situations before. Even if it dawns on me to dress up, I’m afraid of feeling awkward by being the only person dressed up. I eventually convince myself that people don’t usually dress up so that’d be the less risky option.
Yet another reason to wear a suit every day — you’d never have to guess about it, and you’d never be under dressed.
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