More than once in my career, I’ve heard the advice to dress for the job you want, not the job you have. This somewhat confusing statement had me in business-appropriate attire the majority of my professional life. Even when I began working from home, I still made sure the part of me that would show up on video conferences looked just as put together as the rest of me would have if I was actually in the office.

With this statement mulling around in my head, imagine my confusion when I decided...