How One Vogue Editor Styled a Week of Professional Outfits That Feel Like Pajamas

Photos courtesy of Sarah Spellings. Design by David Vo.

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I’m not always proud of my work from home outfits. A few weeks ago, I tweeted that my OOTD was, in fact, a fancy pajama top, no pants, and shearling Birkenstocks. One thing I love about working from home (and doing most other activities from home) is that it really is intuitive dressing: I’m wearing what feels good in that moment, and I can change it at any time. If I want to wear a giant t-shirt, I can. If I want to wear a metallic tea-dress that really should only be worn for formal occasions, I can! There’s no pressure to follow trends or dress codes as long as I look presentable on Zoom.

That’s the freedom. But I loved the ceremony of getting dressed in the morning for an audience, where I could rationalize putting on a top that maybe I couldn’t raise my arms in, but it just looked so fabulous how could I not wear it? Isolation has revealed something new: I’ve realized what I actually need from my work clothing. The reality is that I do work better when I am dressed in something that makes me feel good. But a tight waistband or a too-tight strap can bother and distract me from my actual work. To be productive, I need to feel like I’m wearing nothing. But I need to wear clothes that make me feel good to get things done. Do you see my conundrum? The clothing that makes up my work from home wardrobe needs to be unfussy, a little slouchy, comfortable, and pretty. I’m no stylist; I’m terrible at layering accessories. But give me a bright red color, a statement sleeve, or an earring that looks like food and I’m on board! While I truly loathe having to describe my own style, day-to-day it is simple with a touch of whimsy.

My clothes need to be able to handle a sojourn to the bed, should I decide I’d like to recline and edit for a few hours; they also need to be suitable for a walk to the grocery store in New York’s August weather. I will only give up comfort if it’s something that delights me—otherwise, it needs to function. I’ve dubbed it “slouchy elegance,” and the moodboard is full of old Céline ads, photos of Solange Knowles at the airport, and wide-leg pants with muscle tees. See one week’s worth of such outfits below.

Monday

If I could marry one fabric, it would be cotton poplin. It’s so comfortable but always makes you look put together. I’d wear this button up with anything, or nothing but tights a la Elaine Stritch. But I am not Elaine, sadly, and so I paired the top with wide leg pants I got for a steal on TheRealReal. I hemmed them myself in quarantine, so if the hems look off, please don’t tell me! This is my “business woman outfit” (I’m sure actual business women are shaking). But despite the relative formality of the top and pants, together they feel like pajamas. Throw on a pair of statement earrings and I’m good for a morning of meetings!

Theory menswear shirt in Good Cotton

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Vince wide-leg trouser

Kendra Scott Sophia drop earrings

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Workaday Handmade blue espresso mug

Tuesday

Oh, this dress. I love this dress. I was working out this morning and so I was running late. This dress is the perfect thing to throw on. It’s a column dress with micro pleats and gorgeously sculpted shoulders. It makes you look like you have your life together. I threw my sweaty hair into a claw clip, and pulled out some face-framing strands to look like Amanda Bynes circa 2007. My friend Stephanie makes these earrings that look like caviar blinis and they bring me so much joy. I did put on platforms for this video, but since I'm unaccustomed to wearing heels, I quickly took them off and wore white Birks whenever I went outside. This is maybe my favorite outfit, and it took me 5 minutes to get ready.

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Mara Hoffman Aranza dress

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Chefanie glass blini earrings

Riviera matte tortoise claw clips

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Birkenstock Arizona Birko-Flor sandals

Wednesday

The best thing I’ve ever bought was a vintage Bruce Springsteen shirt from my favorite vintage shop in Dallas, Dolly Python. It goes with absolutely everything, and people always tell me their Bruce Springsteen stories when I wear it. I wore it today with a simple slip skirt from Universal Standard, and the official Vogue-editor slipper, the shearling Birkenstock. My favorite earrings are from Agmes, and look like cute little Brancusi sculptures. Easy, breezy, beautiful.

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Universal Standard CeeCee midi bias skirt

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Vintage Bruce Springsteen Born in the USA tank top

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Agmes Luna earrings

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Birkenstock Arizona shearling sandals

Thursday

This dress is from a super cool sustainable New Zealand brand called Kowtow. I think it’s supposed to just hang like a trapeze dress, but I like that it hugs my curves a bit. To tone down the sex appeal, enter the sweater. Yes, it’s preppy but so am I. The sweater used to be my boyfriend’s, but I have stolen it. When I don’t wash/style my hair, I just run some texturizing spray through it and this Oribe works well and smells so good.

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Helmut Lang twist-back stretch crepe midi-dress

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Pangaia lightweight recycled cotton sweatshirt

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Oribe Dry Texturizing Spray

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Kes Peace mask black cotton

Friday

This dress is old Céline, which I got off TheRealReal. Most of the new clothes I buy are secondhand, and I’ve been enjoying collecting some items from my favorite designers that I wouldn’t be able to afford otherwise. When I got this dress, I texted my mom that it looked like a hospital gown, which it does and that’s why I love it. It breaks my “no fuss” rule, because it has to be buttoned up the back, which requires a second set of hands. But with some sculptural earrings, minimalist flip flops, and a berry lip, it’s truly an outfit that delights me and makes me feel like my most glorious self. And isn’t that really what we want from our clothes?

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Another Tomorrow belted organic cotton-poplin shirt dress

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Tkees Riley flip-flops

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Timeless Pearly mismatched pearl & glass gold-plated hoop earrings

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MAC Cosmetics Satin Lipstick in Rebel