Office Apropos: Styling Slip Dresses for Winter and the Curse of Shiv Roy’s Pants

Office Apropos

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 last Thursday.

Oh and, if you haven’t already, go take a peek at what we wore last week on Wednesday and Tuesday.


This was a fun one! I went to a workout class before coming into work, sweated my boobs off, did not shower or change out of the t-shirt I was wearing, but did replace my leggings with high waist black jeans, and festoon my sweaty t-shirt with this very warm Cecilie Bahnsen cardigan. It’s kind of the unsung hero of my closet—one of those things you get on a whim, wonder if you’ll wear that much, then find yourself returning to over and over again. Don’t you love when that happens? It’s like discovering a new dimension of your interests, or something. The slingbacks are by The Row.


I love this outfit, mostly because it embodies my lifelong goal of figuring out how to style a slip dress in a way that feels “me” (I’ve historically struggled with this seemingly simple endeavor). Turns out the answer is wearing one in the winter with an oversized cardigan and tall boots that you bought at Barney’s with a gift card exactly one week before said gift card was no longer valid for use (RIP).


Eliz told me that she liked my color palette today and it made her want a mocha latte, I’ll take it! Back again with my favorite jeans of the moment and I’ve also been wearing these boots non-stop since I got them. The jacket was a rogue impulse purchase from Century 21 the other weekend, I love it so much. I was mostly in the office all day and was suitably snug.


“I’m the highlighter at the bottom of your pencil pouch.” That’s it. That’s the whole tweet.

Okay, fine, I’ll say more. Writing utensils weren’t necessarily the inspiration for this outfit but it does sound pretty creative so let’s go with it. These pants, in all their blinding joy, were yet another find on The RealReal, but I must admit, I had no dang clue how bright they were until I could practically see them glowing through the box. <3 They’ve been lighting up my life ever since. <3 (SOMEONE STOP ME.) Moral of the story, don’t ever be afraid to leave the house looking like one of those magic pens that can change ink colors with the flick of a button. You know the ones. Lean into it.


Office Apropos
Vintage '60s sweater vest -- similar here, vintage '70s pants -- similar here, Nike shoes
 Vintage '60s sweater vest -- similar here, vintage '70s pants -- similar here, Nike shoes

My coworkers are good at coats. I mean reaaally good. I have one very cool coat in my closet (which it did not occur to me to wear), but other than that I am sorely lacking. Therefore, I mostly approach winter style based on how I want to feel in the office after removing my outer layers. This ’60s vintage sweater vest fits like a glove and, as such, IS SO WARM. It beats a drafty office building any day. I paired the vest with 70s wide-leg pants from Seven Wonders to fully lean into the “candy cane” of it all. The sneakers are Air Max 1s, in dire need of a clean and also the most important things in my life. I highly suggest.


Since the mania of Succession season two hit, I’ve been finding it hard to wear these Frankie Shop pants without feeling like a budget-version Shiv Roy. I got this Naadam sweater a few weeks ago and hadn’t thought about pairing it with said pants until this morning—I’m quite happy with the result. I’m still definitely treading the line of Sarah Snook cosplay but I’m okay with that.

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