02 Aug The (Good?) Old Days – Part X: Dressing Down

The great TV show Mad Men reminds us of an era when it was very simple for men. Put on a suit and tie and go to work, or get on a plane, or go out to dinner, or pretty much anything else for that matter. Heck even Mr. Rogers kept his tie on when he swapped his jacket for a sweater. Women worked in skirts and dresses and you did not see their toes. It was not fun for me as a summer intern in law school riding in two non-air conditioned subways to work dripping wet in my suit. The unwritten rule: after around 3:30 PM you can loosen your tie.

In law firms when I started the only time you could dress down was on the too many weekend days you spent in the office. Maybe wear khakis and a button down shirt on the Friday before Memorial Day. So what happened? The Internet era for the most part. Our clients started showing up in ripped jeans and T-shirts, and we looked out of place. It started slowly with casual Fridays (many firms felt the need to post a sign at reception warning guests it was a dress down day). Then it just sort of happened. Now virtually all big companies and service providers are “business casual” all the time. Many let you go further on Fridays with jeans, etc. Many still choose to wear suits, as I do when I have important meetings. And we do still see “business attire” required at some charity and other more formal affairs (and of course weddings and the like).

But this trend also led to restaurants, private clubs and the like lowering their dress codes. There are still a few holdouts, but I’m not aware of any restaurant in Manhattan that requires a tie (some still require a jacket). The challenge, especially for men: dressing properly when you have way too many choices to mess it up. For women it’s learning where the limits are and what you are comfortable with. For me, whoever declared men should wear knots around our necks should be severely punished. But many do say that we all look better when we are more dressed up. And that’s probably true.

It’s good to dress comfortably, but it’s nice to look nice. Overall, though, I say dressing down wins.