The Year of Dressing Dangerously

Several years ago I started to wear a sports-coat regularly. I wasn’t sure why I was doing this, some vague desire to dress more conservatively perhaps. I certainly didn’t really know how to dress in a more traditional manner. So, a discouraging comment from a friend and the experiment was quickly put to an end. I returned to the drab, overly casual wardrobe that is the mark of the contemporary American man. (You might think that being a software engineer I would be extremely conscious in the way I think things through. For this programmer at least, it doesn’t work like that at all. I very often sense the solutions to knotty design problems before I can articulate them and, in general, think through things in a rather indirect, impressionistic way.)

Then one year ago, I read Jeff Tucker’s article How To Dress Like A Man on (also see his Addendum). With the passing of a few more years I had solidified my reasons for why I wanted to dress in a more traditional manner but still didn’t know how. Jeff’s article gave me the basics I needed but somehow was never taught. My wife and I went out that night, picked out a sports-coat and the next day at work I was in jacket and tie and have been nearly every day of the year since.

For some this might be no big deal, but for me this is quite a change. I grew up around hippies. Due in part to this, I was aggressively casual and always resented dressing up. I found dress shoes to be uncomfortable and thought ties would strangle me. To be fair to my younger self, I think I was typically wearing shoes that I had outgrown. I now know that dress shoes need not be torture. During my undergraduate years in college (1987—91) I usually didn’t wear shoes at all in the warmer parts of the year. I kept sandals stashed under the driver’s seat of my car in case I needed to go into a restaurant. So you can see why the first time one of my oldest friends saw me dressed up and heard that I was dressing like this every day, he said, "Who stole my friend and replaced him with an alien?"

To make my little transition all the more awkward, I work at a small software company that prides itself on a casual, relaxed work environment. The software industry was established in California after all. The CEO is often in shorts and a t-shirt. I am usually the only one at work wearing either a jacket or a tie, much less both. In the first few weeks of dressing more formally, I received several discouraging comments from managers about my new wardrobe. One coworker looked at me with frank horror when he saw my tie. I took Jeff’s advice and just made self-deprecating jokes when people asked why I was dressing differently.

The one difficulty I did not foresee was the trouble I caused my wife. It was enough of a problem that I was suddenly dressing differently, causing her to need a slightly different wardrobe to match, but she was also pregnant (with this baby) most of this last year which causes wardrobe difficulties for a woman at the best of times. To make it trickier, I grew up around hippies but her parents were hippies.

As I worked on expanding my new wardrobe, I received invaluable advice from Ask Andy About Clothes. See, for example, his brief article, Ten Most Common Men’s Fashion Mistakes.

Why Dress Up?

In his article, Jeff explained the how but only briefly addressed the why. Here’s some of my thoughts over the past year on why to dress in the traditional way.

Look at the old movies, (from the 1950s or earlier). Men are just about always dressed in jacket and tie unless they are depicted doing manual labour. What changed? I would say it was the cultural revolution of the 1960s… An egalitarian, anti-traditional cultural moment that gave us wonderful things like high levels of divorce, better thinking through hallucinogens and whole new families of frightening sexual diseases. Why continue something that came out of that?

My wife and I have realized, by the way, that women who want to dress more traditionally are in a worse fix than men. Though worn far less than they once were, men’s suits haven’t really changed in a hundred years. Fine men’s clothing can still be bought. But for young women, hooker chic reigns.

The traditional suit and tie are the culmination of many generations of development that have resulted in an outfit that makes most men look fairly respectable even if their body isn’t giving them much help. Fashion is a perfect example of an area to apply Burke’s recommendation that we ought to benefit from the wisdom of generations rather than rely on the trends of our passing historical moment. I’m the last one who thinks he has the fashion genius to go beyond traditional dress for men and come up with something superior. So, with that final bit of prodding from Jeff, I finally bent the knee and submitted to the results of a slow accumulation of knowledge over generations of how a man should dress so as to complement his looks and convey the right message. There is no question in my mind that in submitting to this tradition I am a far better dressed man than I was under my own weak fashion guidance.

Earlier in this article I emphasized the negative responses, but I have also noticed that I get a lot more smiles from folks now, especially older ones. There has been a subtle shift in the treatment I receive from people at stores, tellers at banks and so many others. I am far more often treated as a serious, professional adult. This is rather nice since I’m 35 now, am getting gray in my beard and have been a professional engineer for 15 years.