A recent article in the New York Times featured Brandee Parker who was once head of marketing for Facebook. In the piece, Ms. Parker talks about the time she and a colleague brought a black suit for her boss, Mark Zuckerberg, to wear on his first trip to Davos, Switzerland, for the annual meeting of the World Economic Forum. They thought that the occasion called for more than Zuckerberg wearing his usual hooded sweatshirt.
Mark never wore the suit. Instead, he put on his Patagonia sweatshirt. (And we are all not Mark Zuckerberg or a CEO of a Fortune 100 company.)
However, I agree wholeheartedly with Brandee.
This does not mean that if I like to wear leggings and an oversized sweater that those clothing choices are appropriate in a business setting. There are many choices today. In fact, a nice pair of slacks and jacket can provide the same comfortable feeling as a sweatshirt.
When I have garnered the respect capital then maybe the leggings will be appropriate. (I saw that Sheryl Sandberg wore them stage for a presentation showcased on the TV show, 60 Minutes. She certainly has the respect capital.) Also, I have learned if my clothing does not feel comfortable and keep me true to myself, then I think twice before moving ahead. I give the same advice to my clients.