I really like Andy from San Jose’s approach to style. Two weeks ago, I wrote a post in response to Vanessa Friedman’s NYT article on changing norms in workplace dress codes. Formal dress codes have relaxed over the last fifty years. However, nowadays men just have to contend with confusing, softly-coded social norms on what they’re supposed to wear. The default: ugly chinos + baggy button-up any time a guy wants to look “dressed up.”
That can sound a little disheartening, but I also don’t think it’s the end of the world if you buck norm and decide to dress a little better. Certainly, you can just make sure your clothes fit (check Jesse’s post on how to find a good alterations tailor). And it’s a good idea to wear better shoes (wingtips, chukkas, or even upgraded sneakers can all be good).
Then there’s Andy’s approach:
I live in San Jose, the middle of Silicon Valley. I skipped the entire "business suit” part of many people’s career arc (save for a very brief spell in the late-eighties). My career has been in software development, almost always for one computer manufacturer or another. Accordingly, I have spent most of my professional life in a polo shirt and jeans. It is only lately that I have taken to wearing tailored clothing to work and elsewhere in my life. I’m lucky in that my employer has no dress code, so I can dress any way I please, although most take that to mean dressing down, not up. But I don’t mind and neither do my colleagues.
Dressing in this way bleeds over into our social life. If my wife and I go out in the evening, these days we “dress up" because we want to. It bothers us not at all if we are dressed more formally than everyone around us. We dress for ourselves and each other and that’s it. We have reached a point in our lives where it is time to be ourselves. If we find ourselves in a place where everyone else is in jeans, so be it.
The main thing holding guys back from dressing better is usually a fear of sticking out. And certainly, sometimes you don’t want the attention to be on your clothes (e.g. meetings, other people’s weddings, and the usual lot). At some point, however, you just have to throw caution to the wind and realize that looking better is going to make you stand out a little. The good news: dressing well can be a joyous thing and other people will usually appreciate your efforts.
