Work Wear: Context and Evolution

The portion of my closet dedicated to business suits. June 2013.

The portion of my closet dedicated to business suits. June 2013.

I’ll know I’ve made it when I can toss all my dressy corporate clothes and wear workout gear full time.

Fortunately, I have slowly grown increasingly more flexible in my work attire, thanks to gradually evolving circumstances: maturity, location, and level of accomplishment. And setting sometimes adds an extra advantage.


When I started my first company, I dressed in a business suit every single day. Partly, this came from a need to counter people’s ageist tendencies: I needed to look older to have other professionals take me seriously.


I started FrogDog in Chicago. Since then, I’ve lived and grown the company in London and in Houston. In the process, I’ve learned that different regions have distinct takes on acceptable professional attire.

In London, stylish and well-tailored clothing—predominantly business suits—connoted status. Chicago didn’t expect the same level of formality as London, but you’d never mistake business attire for casual wear.

Yet if you wear a suit in Houston—except in specific industries (like banking)—you appear to try too hard. And trying too hard looks suspicious. Houstonians look at watches and cars to gauge legitimacy. You can wear jeans and a nice shirt in Houston and get taken perfectly seriously by other professionals—as long as you have a nice vehicle and a status watch.


Different industries and offices have particular cultures and styles. For example, everyone knows technology companies lean toward uber-casual attire.

If you visit or work in an office, you should wear similar attire. People want to work with people like them. Heck, people like people like them.


Steve Jobs could show up—and be welcomed—at a White House gala in his trademark jeans and black turtleneck.

Because he was Steve Jobs.

When you haven’t yet accomplished much, you need to send as many signals of accomplishment and professional polish as possible. As you achieve more, you need to prove less.

What have you noticed about workplace attire?