In August, I retired from from the world of working-for-someone-else/going-to-the-office-everyday and went back to where I belong: self-employment and working from home. This has lots of perks: no commute, better snacks, hanging out with the cats, getting laundry and slow-cooker meals done while I’m working. But there’s one challenge I hadn’t thought much about until I made the decision to retire:  what to wear every day.

I’ve always had very specific rules for working from home, and #1 is Get Dressed. This means putting on actual clothes–not yoga gear, or gym shorts, or a different pair of flannel pajama pants, but clothes I’d wear if I left the house. I’ve never required myself to wear shoes or any particular kind of outfit, but getting dressed has always helped me remind myself tht the work day has begun, even if I only work for an hour and spend the rest of the day knitting or reading or going out to eat.

When I was growing up, my father had his psychiatric practice in our house and he had a firm schedule that I can still recite. He also had a rule about what to wear: a jacket and tie for the first few appointments with a new patient to make sure they took therapy seriously and then no jacket for the duration. But he always dressed as if he was going to an office because, of course, he was–it was just an office in his own house.

I know lots of people who work from home and I know I’m unusual in my strict adherence to my father’s rule. Not even my sister, who’s worked from home for decades, always puts on real clothes. But you may also remember that I’m the kind of person who wears mascara to sit on the couch all day streaming movies, so there’s that.

This time around, I’ve  got an additional, um, wrinkle in my choice: 11 years worth of things I bought to wear to the office where I worked as a university administrator.  Hardly any of that wardrobe qualifies as “office wear”–it’s mostly based on the principle that I do better at everything if I like my outfit–but there are a lot of dresses and skirts, lots of pants that aren’t jeans, and a whole lot of shoes and boots. So now I have to confront some truly existential questions:  Is it really stupid to put on a dress and tights to sit at the computer in my study? If I’m not leaving the house, should I keep wearing my fall shoes instead of switching to boots when it snows? and do I really need to wear anything on my feet beyond what’s required to keep them warm?

Today is Sunday, so I’m feeling good about my outfit: pink/white/yellow plaid flannel pajama pants and an old yellow cashmere pullover sweater with one sleeve altered by Alma, The Cat That Eats My Clothes. No socks or shoes, but I did put on new toenail polish the other day (Chanel Pirate, if you must know). Come back every day to follow my struggle to figure out what defines appropriate work-at-home wear, what I should put on in the morning if I know I’m going out later (same outfit all day or change before I leave?), and when I’ve crossed the line from a person who wears mascara for gardening to someone who’s wearing way too much eyeliner considering nobody’s going to see her for the next two days.