Hot Take: Dress For The Job You Want
Thoughts on WFH wardrobes and at-home outfits
CHERRY ON TOP 🍒 is our monthly newsletter exploring the ins and outs of everything that modern businesses need to truly shine. We dive into topics that live at the intersection of our two companies – ORCHARD STREET, a venture studio + angel fund & DALY, a comms+ agency – as both help founders get the best ideas out into the world, through outstanding operations, comms, and culture-building.Alex here! This is perhaps controversial, but I was never one to do the sweatpants / pajamas thing when WFH kicked in.
As someone who copes with a chronic anxiety disorder, wearing shoes and pants with a desk setup helped me feel in control, put together, and centered.
But my t-shirt and jeans uniform has gotten a bit tired, so I have had my eye on fashionable people in my orbit for work’y outfit inspiration. Enter Erika Veurink, writer behind fashion Substack Long Live. Her stories are chic & cozy — exactly what I need for a fresh new WFH fit vibe in 2025.
And I have been inspired. Now I mix a Rachel Comey sweatshirt with comfortable khaki shorts; a vintage cotton top with a pop of color that brightens up my screen and day; an oversized button down with loose jeans. It works for Zoom, and it works for me.
Now over to Erika, to dish on WFH attire, and dressing for the job you want.
Erika: I think about clothes all the time. It’s my job, but it’s also the container through which I see the rest of the world.
When I graduated from FIT, I pictured dressing myself in pencil skirts and sensible heels for a commute into a Soho office. After signing an employment agreement, I spent a sizable amount of my impending $42,000 paycheck on the kinds of outfits I thought would equate to being taken seriously in an office.
Only, that never happened. I became a writer and found myself babysitting most afternoons, lugging toddlers home from school in sneakers and vintage t-shirts. By the time I was writing full time, I realized my office-centric fantasy would never come to fruition.
The argument that changing out of your wrinkled pajamas can alter the course of your entire day has already been made. Same with the jokes about pairing a fancy top with sweatpants for a Zoom meeting. But that innate desire to pull together an outfit – to construct a wearable billboard of how we’re feeling about that world on any given day – that’s a conversation I still find myself having with friends.
In an attempt to cure myself from the WFH outfit blues, I joined a coworking space, knowing the work outside my kitchen table would mandate a Real World outfit.
But your own closet reinvention doesn’t have to be that dramatic. Even if you’re not looking to make a change to your WFH environment, here are four places I’d start:
Comfortable, chic pants
There is a great shortage of good, unstructured pants on the market today. My advice is to shop secondhand for these. You’ll want something with an elastic waistband, but trust me, this doesn’t automatically resign your look to your gym teacher’s uniform. Try searching for vintage Adidas sweatpants from the boys section in unexpected color combinations. Karate pants are a favorite of mine and come in a ton of sizes and inseams.
If you’re deadset on something that buttons and zips, try workwear from Carhartt or a pair of denim overalls. Jeans can get mundane. Taking creative liberty with your bottoms is step one to an inspired outfit.
Shoes 24/7
Wearing shoes while I work is a habit I picked up a few years ago. In the winter, it’s a pair of Ultra Mini Uggs I only wear in the house, but otherwise, it’s just what I plan to have on for the rest of the day. It makes me sit up a little straighter, knowing I’m not crossing socked ankles during a client proposal meeting.
Bonus: an afternoon walk is halfway assured when you take the first step (of putting on shoes) out of the equation. Wearing shoes makes you productive. And it helps you get out of the house. Planning an impromptu dinner or walk in the park with a friend works too when it comes to upping the outfit ante.
A jewelry uniform
Slipping on my watch, long charm necklace, and stack of wedding bands signals to my body that the work day is about to begin. When I slip them all off after I’ve shut my laptop, I know it’s time to rest. Sure, it’s a little Pavlovian, but I don’t have a briefcase to drop by the front door while the children come rushing in to greet me. This is my way of breaking up work from home and life from home.
Create your own sense of routine with accessories. It’s a great way to make use of what you have and create a signature sense of style in a low effort way. To facilitate the routine side of things, I keep my everyday jewelry on a tray next to my keys.
What an OOTD pic can do
I keep an album on my phone of outfits I’ve worn and loved, as seen in my lobby mirror. We could all benefit from documenting our outfits more. It teaches us what we love to wear, what shapes suit us, and what combinations we can count on when getting dressed feels overwhelming. This can be as simple as snapping a picture of your outfit in the lobby mirror on your way out to grab a coffee.
Next time you’re stumped on what to wear, revisit this paper doll-esque album for real life inspiration from your closet.
Getting dressed in a Real World outfit has the power to shift a regular WFH day into an adventure waiting to unfold.
The Cherry on Top: To get you started on your level-up WFH wardrobe journey, set an alert on TRR for comfortable pants you know and love in your size and preferred color. Or send an SOS to your group chat with my favorite prompt: What are your favorite non-jean pants?
Erika Veurink is a writer, brand consultant, and founder of EV Salon, who lives in Brooklyn by way of Iowa.
Dream crossover ep!!
The only thing I love more than a jewelry uniform is a Malin selfie! xx