Sloane Crosley
Credit: Skye Parrott/Trunk Archive

When I left my job in publishing in 2010 to become a full-time writer, I took a list of contacts, a lifetime's supply of ballpoint pens, and my unwavering belief that so long as I still dressed for the job I no longer had, everything would be fine.

Having only ever worked from my apartment when I was convalescing, I was dubious of my freelance self. Would I sleep until noon? Consume buckets of coffee like Balzac? Start writing at 3 A.M. like Hilary Mantel? Sit in the dark, subsisting on string cheese and whiskey?

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The one piece of my new life over which I had total control was how I dressed. Paranoid about the wheels coming off if the heels came off, I started dressing even better than I had while I was commuting to an office. And thanks to the Styles section of The New York Times, there's a public record of this bananas time. The paper asked me to keep a diary of my outfits over the course of the first week of 2011. While my bathrobe made a cameo, the real stars of the diary were Balmain scarves, Chloé pants, Prada platforms, and zipper-laden dresses. As if this weren't enough, I also copped to changing clothes in the middle of the day to go to the library. To the library.

Naturally, this overcompensation couldn't sustain itself. For one thing, I'm a writer who used to work in book publishing. I am successful enough, but my surname is not Rowling. My designer roster is limited. For another, it's idiotic for one to subsidize one's dry cleaner just because one has decided it's somehow vital to write in a linen jumpsuit.

Thus, despite my fears about structure, my sartorial pendulum swung in the opposite direction. My period of extreme overdressing was followed by a period of extreme underdressing, during which, if I left the apartment at all, I wore threadbare leggings, shabby sneakers, and stained T-shirts. When I encountered someone I knew, I'd offer the white lie that a stranger had "just" spilled her coffee on me. And seeing as how I was no longer tied to one location for nine hours a day, I could commit to this narrative for days on end.

And yet I worked. I was productive. I did not watch the countless hours of QVC programming that my outfits suggested. The problem was, I never quite felt like me. Which is why I left my job to begin with—to travel down a path that was closer to who I was. I couldn't do it in heels, but as it turned out, I couldn't do it barefoot either.

If I was to leave the apartment ever again (or, really, just answer the door for UPS and food delivery), I was going to have to figure out how to dress for Existence 2.0. Six months into my freelance life, I looked inside my closet and was confronted with a binary rack of cocktail dresses and pilled shirts. I saw that what I really needed was pieces that had my style but were built mostly for an audience of one. A Goldilocks wardrobe.

I started simple. Tops from cult brands like Humanoid and James Perse became my friends. They smacked of relaxed style. These were followed by pants with actual zippers, instead of drawstrings, from Sandro and heretofore unexplored corners of J.Crew (a chambray shirt isn't necessarily right for the office, but since it doesn't double as a dishrag, I had never owned one). And much to my delight, once I paired a Rachel Comey blazer with my ratty T-shirts, they didn't look so ratty anymore. They looked like ... me.

So I began to make more significant investments. I purchased a pair of elegant flat Frye boots that were easy to put on (footwear can feel like an undertaking when you work from home). Six years later, they still make me feel like a celebrity running errands, as do the cardigans from Acne Studios and Vince, the kind that, once bunched at the elbows, are given a renewed sense of purpose. But my favorite foray into freelance flair is a wide-brimmed suede hat from London's Lock & Co. A writer's best friend, it's the answer to every bad hair day I detect only 10 minutes before I have to appear in public.

Now that I feel secure in this life, I do allow myself to slip into the slovenly on occasion. But it's a break from how I normally dress, not a potential life sentence for how I will dress. Three books later, with another on the way early next year, I also know that all those work-from-home clichés can be deceiving. Yes, you often get dressed later in the day. But it's because you have the capacity to make your bed your desk. Sometimes you're in a robe until noon because you've accomplished more than your suited counterparts will all day. And now, when I take a coffee break, I slip on a pair of skinny jeans and tall boots, careful not to slosh my drink all over myself. Gotta look presentable for the boss.

For more stories like this, pick up InStyle's April issue, on newsstands and available for digital download now.