The Chic Freelancer’s Wardrobe Does Not Include Sweatpants

A longtime proponent of the office job with an affinity for planning my next-day work outfit as a sort of meditative bedtime mantra in lieu of counting sheep—blue jeans, blazer for client meeting, those stacked-heel booties for that post-work date, ommm—I recently switched professional gears and found myself simultaneously juggling a few freelance projects, most of which could be easily managed from the comfort of my living room. The initial couple of months were fantastic: My skin was glowing from its makeup-free regimen, I relished in being the only one of my friends not to need snow boots during the winter storm, and a small fortune was saved that would have otherwise been spent at Barneys. I realized that with a few notable exceptions, I had pretty much survived the entire winter in one stretchy pair of Frame Denim jeans and an assortment of cotton marinières—and not of the cool La Ligne variety. The real wake-up call came when a guy I was seeing asked me to a benefit and seemed quite relieved when I arrived looking relatively put-together in an ensemble (Thakoon pencil skirt, Céline heels) left over from my days of chic Parisian office attire. Later that evening, he confessed. He had been worried. Apparently, during a recent mid-work session rendezvous at the Bowery Hotel, I had “looked a little rough.” Rough how? “Oh, you know . . . like you hadn’t washed your hair.” A small part of me died. Had I really fallen subject to the standard cliché of the millennial freelancer: in perpetual pajama party mode, schlepping around coffee shops with a Carhartt beanie masking her dirty mane? Redemptive measures had to be taken, and quickly. I decided to ask my other freelancer friends, all poised women whom I had never seen leave the house sans manicure, on how they manage to avoid the seemingly inevitable sartorial slump that comes with having nobody to answer to but yourself.