Office Apropos: 6 Winter Outfits Inspired by Instagram, Couture Week, and More

Welcome to Office Apropos Winter 2020! It’s the first Office Apropos of the decade and the second in our new publishing format, in which we share the outfits we wore to work one day at a time. Below are six outfits we wore to work on Monday.

And might I suggest checking out what we wore to work last week on Tuesday, Wednesday, Thursday, and Friday.


I saw a picture of Camille Charriere in her Instagram stories wearing a blazer over a white button-down with a sweater over, a mini skirt, tights, and jewel-encrusted sandals then thought to myself: I love this. I dress like this. I want to wear this. So I swapped her skirt for jean shorts and sandals for boots eyyyy voila: an outfit to take me from breakfast in Soho to office in Noho to dinner in Flatiron with a brief interlude for kids around 5:30 p.m.


This outfit is the rare product of me actually laying (well, in this case hanging) out my clothes the night before, because I was so excited to wear this new smocked top from Doen that is technically intended for springtime but easily winterized with the help of a cardigan and wool pants. I was very stuck on what shoes to wear though, and I don’t think sneakers looked quite right, but I didn’t have anything else that was better. Please advise in the comments if you have any ideas. To their credit the sneakers did shepherd me along my morning commute quite comfortably and made me feel less stuffy when I traversed the Williamsburg bridge for a dinner later in the evening, so there’s that.


A friend from Turkey introduced me to this designer who makes these amazing faux fur coats and I’m nothing if not a simple-outfit-with-a-wild-outer-layer kind of person. Then surprise, surprise these jeans and boots make another appearance, it’s most definitely a uniform at the moment. Perfect for a full day in the office followed by a night at home with zero plans for literally the first time in a full week. I cooked, read, and was in bed by 10 p.m.


Mango pants, vintage cardigan -- similar here, thrifted shirt -- similar here, New Balance sneakers Mango pants, vintage cardigan -- similar here, thrifted shirt -- similar here, New Balance sneakers

You know what? When I planned this outfit in my head over the weekend, it did not involve the button-up underneath the cardigan. It didn’t even involve the button-up at all. I guess I was feeling a little ~crazy~ this morning when I woke up and just went for it. Glad I did, though. I am both warmer and prouder because of my layering techniques. Once again, my favorite pants but in the OTHER color, have made their debut. These are—and I cannot stress this enough—my new closet staple. They’ve set a new high that is hard to beat. The cardigan is my newest vintage baby. And she has a bow. Isn’t that precious? I don’t necessarily identify myself as such but with this cardigan I feel like I can be anyone I want to be. And today I want to be precious.


I had one of those mornings today. I was hellbent on wearing an outfit I’d envisioned the night before, only to find the real thing looked NOTHING like its profile picture (a.k.a. my imagination). Cut to 25 minutes later, every sweater & pair of pants I own is strewn across the chair I had just cleared of laundry and I am still unconvinced. In these situations, I find it best to return to the tried and true ‘fits that never fail you. Entrè vintage balloon jeans, white turtleneck, and red lip (for confidence). Doubling down on confidence boosters, I went for my fluffy, takes-up-too-much-space-on-the-L faux sherpa coat that moonlights as an office blanket.


I woke up with a cold today, so I was feeling very uninspired while getting dressed. The only things that got me feeling slightly excited were these new Weejuns (bought on Eliz’s expert recommendation) that arrived over the weekend and this story we published today, which featured a white-socks-and-loafers Chanel couture show look. I bought this jacket from Zara when I moved to NYC in 2017 and I get asked about it so much—it’s one my favorite fall or unusually-warm-winter-day staples.

Team Repeller

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