Fashion & Beauty

WTF Do You Wear to WFH? One Writer Finds Out

Toronto-based writer and jewellery designer Anna Stainsby dressed for success for one week—here's what she discovered about herself and her style

It’s a truth universally acknowledged that working from home is a recipe for sartorial sloth. I wish I could say otherwise. I could pretend that the glamour of my current status as a writer/jewellery designer/graduate student translates seamlessly into colourful and exciting outfits—but it doesn’t. In truth, my work-from-home fashion leaves *a lot* to be desired. Unless I have meetings, customers to see or classes to attend, my style is what I’d describe as “comfy”—which is really just a cute way of saying that I live in sweatsuits

That’s not to say I don’t like dressing up—I do! But part of the fun of dressing up is experiencing the world and everything that goes along with it. (Other humans! Fresh air!) So if I don’t plan on leaving the house, I see a good outfit as a waste—like painting a picture that no one gets to see or baking a cake that no one gets to eat. In other words, kind of sad.

The truth is, as cozy as I may be in fleece-lined clothing, it doesn’t make me feel like me. As someone whose professional and academic careers are creatively inclined (I’m currently doing a master’s in creative writing at the University of Toronto and am the founder of and designer behind Neophyte Jewels), I started wondering if maybe starting my day with a little more intention and creativity might manifest itself in other areas of my life. I decided to document a week’s worth of work-from-home outfits to find out whether dressing well *really* affects my productivity. 


work from home outfits: the writer poses for a selfie in a striped sweater, with a bib, bike shorts and gold sandals

The writer in her first WFH outfit

I tend to start my week off by filling orders for Neophyte that accumulate over the weekend, so Mondays are generally spent at home making custom pieces and packaging. It’s a pretty nice way to ease into the week.

Ever since I got my paws on this sweater (an insane deal at Aritzia), I’ve pictured it with bike shorts. When I told my boyfriend about it, he asked what season I planned on wearing this combo. And then it occurred to me: It’s the perfect at-home outfit! Bike shorts are ludicrous for winter/early spring— unless you never plan on leaving your toasty apartment, that is. I didn’t have any appointments for the day, so I committed to summer from the waist down and Scandinavian baby up top. It ticked all my comfort boxes and I managed to write even more than I’d set out to. I credit the bib.


work from home outfits: the writer poses for a selfie in a chunky oatmeal coloured sweater and navy slip dress

This term, I managed to squeeze all my courses into one long day, so on Tuesdays I’m actually out and about in the world. It was a balmy 4 degrees outside, so I laid my groundwork with a silk slip, tights and Oxfords. To balance everything out (the Victorian in me truly thinks that even a semi-exposed ankle is incredibly sexy), I threw on a huge chunky knit. Fun fact: The knit is older than me, and the it’s warmest thing I’ve inherited from my mom. Despite the fact that I actually wasn’t at home all day, this is still a perfect WFH fit.

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work from home outfits: the writer poses for a selfie in a blue suit and tie dye cropped sweater with white sneakers

When I initially saw this suit at a vintage store, the elastic waist felt a little too geriatric. But then I tried it on and, man, an elastic waist is one *underrated* feature. It’s such a light suit that I wear it mostly in the spring and summer, but it was truly perfect for lounging in at home. Plus, there’s nothing like working while wearing a full suit—for some reason, I was less tempted to crawl to the couch or take a nap. My brain just activates “biz mode” and then I’m off downing coffee and crunching numbers.*

*FYI, the numbers thing is a figure of speech.


work from home outfits: the writer poses for a selfie in a black lace dress, black mules and a purple sweater tied diagonally across her shoulders

I had lots of edits to do on my thesis on Thursday, so I tried to conjure up a “writer’s outfit” to inspire me. Because my master’s is in creative writing, my thesis is actually a novel, which is both really fun and a big undertaking. I’m always looking for productivity hacks (waking up at 4 a.m. or wearing a writing hat are just a couple that I’ve tried), so I thought I’d see if dressing the part would work.

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The aesthetic was Victorian (High neck! Lace! Ankles!) meets Latina (a pop of colour and vintage gold hoops). I always try to imbue my writing with my Honduran heritage, so I tried to translate that in my style as well. It was a pretty productive day, but I do have to credit lots of coffee and a sugar rush courtesy of a cinnamon roll from The Danish Pastry House for at least *some* of my stamina. 


work from home outfits: the writer poses for a selfie in blue jeans, a ruffled white top and gold jacket

This last outfit was my casual-Friday take on Chanel designer Virginie Viard’s final-bow outfit at the spring/summer 2020 show. I’m currently breaking these boots in, and after countless blisters and blood-soaked shoes (talking to you, Doc Martens) over the years, I’ve found the easiest way to do this is to just sit around and sweat in them all day. Since I only had school readings to do and a few orders to fill, I did just that! And I’m happy to say the boots fared well on our one excursion to the post office—and got lots of compliments from the ladies who work there. 

The verdict

Working for yourself means that you’re never really off. And that can be challenging. I’ve learned that sometimes I have to physically turn my phone off, make a non-work-related outing and enforce boundaries for the sake of my sanity. 

But I’m beginning to see that taking a moment in the morning before diving into the thick of writing/reading/creating can also be a way to care for myself. Picking out clothes that either have something to say about what I want to accomplish or how I want to feel can be a physical way to set the tone for the work I’m about to engage in. Not to sound like I’m therapizing myself (though I guess I am), but a little moment of sartorial intention is another way to nurture my artistic expression.

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And even if some of my outfits don’t get to see the light of day, maybe, just maybe, enjoying the process of putting them together is enough. 

Isn’t the process what it’s all about anyway?