Dress Up or Down? The Great WFH Debate

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I’ve been a work-from-home entrepreneur for nearly my entire career; eight years to be exact. In that period of time there has been one comment that has popped up more than every other quip combined— ‘It must be nice to work from your pajamas all day!’

Early in my career, I took intense offense to this innocently made remark. I’d try to be gracious in the moment, knowing that unless you were in a similar boat to my own, you may not understand why a casual statement struck me as so frustrating.

Usually, I’d brush it off with a smile and some sort of affirmative mumble—sometimes I’d come up with a pithier remark, trying to explain in a sentence or two why “there’s a lot more to it than that.”

But, then again, I’d worry was I a hypocrite? There were, probably the majority, of days that my attire consisted of, at worst, a messy bun and, yes, my PJs— and at best, I’d toss on a pair of yoga pants and a t-shirt to feel a little more ‘dressed up’ or ready for an errand.

In my life before WFH, and in my out-of-work life, I have always considered myself to be well dressed. I’ve had a borderline obsession with high-fashion since childhood, and, I’ll admit, I have a collection of designer clothes that spend way too much time on a clothing rack.

What frustrated me most about that flippant PJ phrase, I believe, is that they were right— that is what I do, and in turn, I'd feel unnecessary guilt about it. Fall into feeling that I’m not put together, or I’m too lazy to make an effort—which was simply untrue.

Do I feel better when my hair is washed and styled and I’ve got on something far fancier than sweatpants? Most definitely, but that falls under the umbrella of self-care, not my ability to do my job well.

When I see my corporate friends in their Instastories dressed up and looking lovely, I do feel a twinge of guilt. But then I try to remind myself of a few more important pillars that make up the content of my character:

  • My clients have never waited an inordinate amount of time for a response from me; they also know I am consistently available during out of work time.
  •  I’ve always gone above and beyond to create the best results for brands that I became truly knowledgeable of and passionate about.
  • I can juggle multiple projects at a time, assuaging different personalities and managing expectations with ease.
  •  I take sincere responsibility for my work and stay incredibly conscientious of how my actions effect an entire team.

Those attributes, by comparison, explain two things; first, why I have had consistent work without having to go back to a corporate job for all of these years, and second, no matter who lines the labels of my clothes, I am an asset to any organization.

So my advice on the great debate on what to wear working from home? Don’t be too underwhelmed by my response— just work hard while wearing what you want; life has way bigger worries for you to think about than if you’re wearing pants in the privacy of home.