Freelancer fashion or “Are you wearing pants?”

One of the more realistic outfits from this tv freelancer. Not a giant flower in sight.

Let’s get this out of the way — when I started freelancing a friend sat me down and said ‘there’s only one rule to this job: every morning, before you start work, make sure you put on some damn pants.’

Okay, maybe she was exaggerating just a little. But it’s true that freelancers have a reputation for doing their work in sweats and yoga pants. Yes, that bed to laptop commute is pretty fabulous but freelancing isn’t just about hanging out in sweats — when you need to interview a subject, attend a press conference or review an event, you need a wardrobe to match.

As friend and freelancer Alexandra Kimball said, “There’s gotta be a happy medium between office wear and the look I’m sporting now — sweatpants, a t-shirt and, like, negative makeup. I look like a suicidal person. What can I wear to write on my couch that I’ll actually want to put on?”

Although I did once write a personal finance piece wearing a ball gown of ruffled tulle that was surprisingly comfortable, forget Carrie Bradshaw: most freelancers do not and don’t care to dress like Sex and the City’s heroine. Instead, think about how to dress stylishly for the everyday with clothes that are comfortable enough to work in and professional enough for the press line.

I asked Christie Ressel, an image consultant and owner of Personal Power Image, about what to add to your closet so you can be comfortable writing on your couch yet still look professional without having two wardrobes.

“Great-fitting jeans you feel good in — preferably dark washed as they transition easily from casual to dressy,” Ressel says. “Try Yoga jeans — they have the chic appeal of denim but the comfort of a yoga pant. I also love DL1961 jeans. They’re a beautiful fit and look really elegant when dressed up!”

If you’re not a jeans person but don’t want to wear yoga pants, Skinny Sweats does a sweatpant trouser. I wouldn’t wear them to the office but throw on a t-shirt and a jacket and they’re fine for running errands. If you prefer dresses, look for jersey or ponte: they’ll hold the shape and look professional enough, especially with a blazer on top.

Ressel also suggests investing in a trench coat in a vibrant colour. “Not only will they provide some shelter from the Canadian climate, but can look chic over casual pieces and cocktail attire.” The joy of trench coats is you can create attitude based on how you flip your collar. Or I’ve been watching too much BBC Sherlock.

Trench coats lead to blazers. It’s understood that a blazer instantly makes you look more polished, even if you were up until 3:00 a.m. finishing that piece because your editor moved up your deadline by a week. With blazers, cost is less important than good fit, particularly across the shoulders (and, let’s face it, you won’t get rich freelancing).

You can get blazers almost anywhere at any price point. However, while finding a decent blazer in plus sizes that looks good and doesn’t break the budget can be more difficult, you can increase your options by ordering online. Although shipping and customs duties do raise the price point, Eddie Bauer offers classically styled blazers in sizes up to 24w. Or indulge your inner fashionista with a paisley print from ASOS Curve. (Remember to check the return policy before ordering so if you don’t love it, you can send it back.)

Once you have your blazer, Ressel says add colour and texture with t-shirts and camis. “A good t-shirt is comfortable for long hours in front of your computer but can be dressed up or down with jeans, slacks or skirts and the right accessories,” she says. As for accessories, Ressel says just mix it up: “Fun, bold pieces in metallic or gem-covered styles take any ordinary outfit and immediately add glamour and interest.”

Finally, shoes — Kimball said one of the best tips she ever got was to keep a pair of good shoes by the front door so she looks pulled together when she takes out the garbage. Ressel acknowledges the glamour a pair of heels gives to an outfit but says flats are where it’s at for freelancers.

“Flats that are chic and cushioning while you race around town to appointments can also save your aching feet when you’ve been wearing heels for hours,” she says. “But don’t cheap out — make sure you get a well-made shoe with some support.”

I’m going to suggest one more thing – a bag that looks good and can carrying all your equipment. That could include your recorder, notebook, laptop (for those writing in a coffee shop days), phone(s), wallet, camera and pens. There’s nothing worse than carrying two big bags (packhorse?) or doing the bag transfer and forgetting that one vital thing – usually your recorder or pen.

Realistically, most of us will continue to wear sweats on the couch and change when we’re going out but, for me, dressing before I start work helps remind me that this is my job. When you work from home and have limitless freedom, it’s easy to lose sight of that. I feel more professional and thus more motivated in my ‘work’ clothes, even if I never leave the house.

It also means that the next time my friends ask if I’m wearing pants, I can say yes. Or say no, because I’m wearing a skirt.

Or a ball gown.


Part of the Free(lance) lunch series. 



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