Freelancer Fashion: Monica Heisey

Katie Capri

As the work day changes, the way people dress for a day’s work has too. Our new series is designed to provide insight into the alt-lifestyle of the freelancer. Now that “creative types” at the helm of the freelance revolution no longer need to hide their true colors under business causal dress codes, we wanted to see what they wear to work when their day job is free from public and professional scrutiny. And then share it with the public.


Writer and comedian Monica Heisey writes from her kitchen in Toronto, turning granules of personal experience with saccharine pop culture, beauty standards, and awkward situations into bittersweet episodes of salient cultural critique delivered with a dry wit and self-deprecation which mask the finger-pointing running under the surface. She also specializes in clear-cut calls to take away the taboo of having feelings. Google closely associates her name with Jake Gyllenhaal for no discernible reason other than this largely overlooked tweet.

monica heisey

The “What if I’m coming from/going to the gym? You don’t know” Look

Line of Work

I’m a freelance writer and work mostly online, for sites like The Hairpin, VICE, Gawker, The Cut, Playboy… basically anywhere that will have me. I’ve had a few office jobs, but typically my work has either been from home… or sort of bizarre and performance-based. The last regular job I had that wasn’t writing involved dressing up in a jumpsuit and pretending to be a bartender on a spaceship for an immersive events company called Secret Cinema. Because of this…

I have almost no idea what an adult person is supposed to wear to work. I don’t even own an “emergency real job interview” blazer anymore.

Daily Routine

My alarm goes off every day at nine but I’m not going to lie to you about getting out of bed before ten-thirty. I usually check my emails on my phone and hang out in bed with my boyfriend and cat after pressing snooze like five or six times. Sometimes I run bad jokes by them for pieces I’m working on. (The cat is not very helpful, but my boyfriend is a comedian, so it balances out.)

From whence the freelance writing came.

From whence all freelance writing came.

Around ten-thirty I make some tea and breakfast and open my computer and actually get to work. If I don’t have concrete plans to leave the house—to meet someone for a coffee or have lunch with my dad or something—my beauty routine is pretty minimal. I very frequently have mascara on from the night before, so I’ll just put on moisturizer and brush my teeth and draw on my eyebrows. I’m too ginger for my brows to be at all visible on their own, and I get really antsy about not having them on, which is such a ridiculous problem to have, but it makes a real difference to how I feel about myself.

“Once my eyebrows are on and I feel like A Normal, I can get on with my day”

Photo on 2014-11-24 at 4.41 PM #2

A ‘let’s get real’ bathrobe.

Favorite Outfits

When I first started working from home I invested in this beautiful vintage kimono and told myself I was going to wear it all the time, just swanning around the house in a silk robe drinking cold brew coffee and making organic lunches and living this gently bohemian lifestyle I had invented as a teen, hopped up on repeat viewings of Moulin Rouge. About a week into this plan, the kimono sleeves had been accidentally dipped into just about every source of liquid in my house and my organic lunches could be more accurately described as “just hummus.” I still keep it pretty cosy with my work clothes. This, for instance, is a less-fancy robe with more convenient sleeves that I wear a lot:

Another classic working from home look is “What if I’m coming from/going to the gym? You don’t know.” Athletic wear is as comfortable as pyjamas, but implies an active lifestyle and positive choices. This is perfect for leaving the house to buy more cereal.

And finally, I’d be lying if I said I didn’t work naked most of the time.

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Home office appropriate nudity

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