Skip to main content

Freelancing: Dressing Up for the Occasion


Two years ago, Whitney Matusiak offered some good advice on BoldFace about wardrobe considerations for freelancers. Today I’m going to sing the praises of dressing up for working (mostly) at home. I am amazed at those who work in their jammies. Amazed in wonder, not judgment. The only things I can accomplish in my nightwear are scrolling through Facebook and drinking my first coffee.

My POV is about preparation, discipline, and focus. I am hyper-organized. I love lists. They are my modus operandi for life and work. In order to be productive, though, I must be “ready for my day,” and the physical must precede the psychological. (See the first point on Emma Gannon’s blog post about being self-employed.)

My dressing up for work at home is admittedly facilitated by having a largely neutral (read: black and grey) palette of similarly styled clothes: no hemming and hawing about what to wear. Once I know the forecast for the next day—our old apartment isn’t climatically smart—it’s easy to select tomorrow’s outfit. Boom—done!

My days-off wardrobe is what my husband would call urban bohemian, and my work clothes also focus on adaptable comfort. I even have a uniform that consists of a little black dress, a grey cardigan that was my mum’s, black stockings, and lace-up Doc Martens. This is my gettin’ ’er done go-to. My morning toilette includes hair product, eye makeup, and some jewellery.

If I dress as if I will be meeting clients and online colleagues in person, I find that I approach my at-desk work with more discipline and tenacity. Feeling pulled together allows me to interact with clients, even electronically, with confidence. It helps my presentation of self in everyday life as a business owner and not a hobbyist—as many of us freelancers are so often (annoyingly) characterized. Some days, I am only interacting with the snail-mail carrier, but if I am suddenly called out to an onsite client meeting or am needed for a Skype consultation, I’m ready.

And what about work at a client’s office? I might out-dress some folks in my formality, but with my walk-forever oxfords, some funky earrings, a scarf, and a hobo bag, my style keeps me approachable, comfortable, and adaptable to any curve balls the day might throw my way. I’d rather look overdressed than convey the wrong impression about my business practices. And I don’t leave the house without a purse-sized lint roller.

Of course, there are days when my work wardrobe model goes out the window, like if I’m feeling sick or have an appointment or a volunteer commitment requiring other types of clothes. But generally, if I show up to my desk in my uniform before nine, I’m likely to have a productive and satisfying day. If nothing else, my self-imposed sartorial strictness mirrors my ridiculously neat desk and organized office supplies. Minus the cat hair, that is. (See lint roller note above.)

Uptight, inflexible, over-the-top? Perhaps. That’s what 12 years in a school uniform will do to you. I wish I could still wear a St. Trinian tunic, but that might inspire literary shenanigans, rather than editorial clarity, consistency, and correctness.


This article appeared on the EAC Toronto Branch’s blog, BoldFace.