Every day, I wake up at 6:45 a.m. when my 4-year-old son jumps onto our bed and screams “COCK-A-DOODLE-DOO.” And after a quick shower, I put on my work uniform: Loft leggings and the most luxuriously buttery Banana Republic Factory T-shirt. (Seriously, I love them.) I drop off my kid, head back home, and sit in my house writing words (including these) all day long. Occasionally, I go outside to get the mail. Otherwise, I am alone all day, usually writing in bed — so all I really need to be, clothing-wise, is comfy. This routine requires a daily trip to my closet, where a decade and a half’s worth of sophisticated work clothes hang there despondently, like so many silk and twill orphans. Honestly, it bums me out to look at them, since I’m never going back to an office. I work from home now, and plan to do so forever.
From 2008 to 2022, I worked for two media corporations, and though my job was creative and the vibe at each magazine fairly loose, the trappings of the parent company never left us: IT trainings and all-hands town halls and this or that portal to check PTO, blah blah blah. In a rigid realm such as this, a person needs a way to express their personality. By my later years of corporate life, my medium was vibrant, patterned, color-crazed clothing. Which is precisely what’s staring at me as I type this in my bedroom.
Gingham slacks, an ocelot-like patterned linen dress, a polka-dot jumpsuit, a silk boatneck blouse in blinding hot pink. What am I going to do with this stuff — be the best-dressed mom at daycare drop-off? Throw dinner parties so that I have an excuse to gussy up? Amid all the insanity of the last two years, there’s been plenty to worry about: When the hell my kid will be vaccinated, when I’ll feel OK about flying again, various coups and elections and wars. I’m aware that this is not a real problem. And yet… every day, I wonder what to do about it. (Best to deal with the stuff I can change to feel more in control, right?)
So, recently, I began investigating sartorial solutions. As I see it, there are three options.
Donate or Sell the Clothes
The first option might seem like the most promising — after all, you may be thinking that there are folks who can’t afford workwear and might benefit from having these. Except we’re not exactly talking about Ann Taylor suiting or Brooks Brothers tweed dresses. Almost none of what I own is traditional office attire, and I question how useful it would be to someone trying to look professional.
Furthermore, I don’t want to get rid of these items. I love them. I spent thousands of dollars buying them and thousands of hours curating them. I’ve logged photos of all of them into a super handy app that helps me mix and match them into looks. And more fundamentally, the personality these clothes expressed is still my personality, and I want to keep expressing it.
Editor’s Note: If you do choose to go the donation route, organizations that accept donations of gently used clothing include the American Red Cross, Dress for Success, Planet Aid, The Salvation Army, Soles4Souls, and Vietnam Veterans of America.
Store Them in the Attic in Case I Ever Have a Job-Job Again
The second plan is a no-go, too, I fear. As I mentioned earlier, I don’t want to have a real job again. Commuting, small talk, meetings that accomplish nothing — I’m done with all that.
Find a Way to Wear Them in Daily Life, Which Is What I Went With
So, it seems the only thing left is to actually… wear my clothes. The key here is to do so without looking like someone trying too hard — one of my worst fears — and without having to be uncomfortable all day. No too-tight waistbands, no itchy sweaters.
I sit down and come up with a strategy. My first step is to develop criteria to help me figure out which garments can work and which have to go. I create two litmus tests. One: Can I wear this to drop off my child and not feel like an overdressed weirdo? Two: Can I wear this around the house without feeling squeezed, chafed, itched, or otherwise constrained? Next, I go full Kondo and donate everything that doesn’t pass muster. I wind up filling two full lawn and leaf garbage bags. Feeling lighter already!
Now comes the infinitely far more fun part: getting strategic with styling. A quick Google search turns up a few ideas for dressing down work clothing — though there’s infinitely more advice for the reverse. Still, I found a few surprisingly doable takeaways.
1. Wear Sneakers, Not Heels
Though some tips — like this one — are obvious, it’s weirdly helpful to have them pointed out to me. Oh, I think. I can wear that gunmetal-hued lace-overlay skirt with black Converse, and it’ll be totally fine.
2. When in Doubt, Get the Denim Out
Denim also plays an important role in de-fancying clothing; if a blouse is too elegant, wear it with jeans. If a dress is too dressy, top it with a denim jacket.
3. Toss T-Shirts Into the Mix
Same with the humble T-shirt, the great equalizer for work slacks and dress pants. Pop one of those aforementioned buttery babies on with a bias-cut silk skirt, and you’re in business (or at least business-casual).
4. Keep Styling Simple
Keep the jewelry and makeup simple and slight. Avoid overt signals of dressiness, like a silk scarf or a gold watch. Incorporate fabrics that don’t read as luxurious, like cotton, seersucker, chino, and corduroy. With all of this in mind, I invent a new rule: For every upscale item that you put on, wear two down-market items for balance.
I take these ideas for a test drive. One weekday morning, I slide on that Italian ocelot-print linen dress. Then I put on a pair of black low-top slip-on sneakers. I keep my face bare except for eyeliner, add a denim jacket, and wear tiny pearl studs. I drive my son to school, where his terrific teacher looks me up and down and says, “You look like springtime!” Which is precisely the note I’d hoped to hit — light, understated, breezy. Casual, but elevated enough to earn a compliment. And most important: entirely me.
