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Diary of a Copywriter: What Not to Wear

Posted on October 5, 2011 and read 4,241 times

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lindsay Diary of a Copywriter: What Not to WearLindsay Smith

There’s a stereotype about people who work in advertising.

They dress in black, wear skinny jeans and Buddy Holly glasses and are covered in tattoos.

Well. There is one thing I always say about stereotypes. They are probably true.

But, me? I like to be different. My manfriend calls it “weird.” Whatever. You say tomato, I say shut up.

I sort of fell into advertising. I was working as a freelance journalist and making about $12 a year when I ran into an old friend from high school at a party. She was a copywriter at an agency.

We commiserated about being English writers in Montreal and the difficulty of finding work. After comparing stories, she suggested I put together a couple writing samples and come in and meet one of the senior writers.

I followed up with her a few weeks later to set up the meeting.

Then that existential question came up. The one that never really has an answer. What do I wear?

Despite my friend’s insistence to dress casually, I decided to wear the exact opposite. Because you know, wearing high-heeled boots that I could barely walk in seemed like a brilliant idea at the time. I paired said boots with a polyester skirt that was part of an outdated suit, a pink long sleeve shirt and white leather jacket. Looking back, I’m not sure why I thought channeling the 90s was going to get me a job.

But it did. And it wasn’t the outfit.

I wobbled into that meeting on my ugly square-toed boots and shook hands with a very stylishly dressed man. I immediately felt overdressed and awkward. After marveling at the fact that he had a couch in his office, I had a seat in it and handed him my portfolio from under my arm.

But before I could say “Doc Martens and plaid shirts,” my cell phone rang.

I rustled around in my purse, apologizing profusely, and turned my phone off while silently cursing my friend Michelle for calling at that exact time.

“Is your ringtone the 90210 theme song?” he asked.

“Um. Yah. Sorry. I meant to turn my phone off.”

“No, no. That was awesome! I love 90210.”

Score. I was in. A week later I met with the creative director. And a week after that I had a job.

I eventually got the hint that advertising was a pretty casual place to work. I’m quick like that. I traded in the polyester skirt for jeans and the ugly boots for sneakers and not-so-ugly boots. But I still kept up a somewhat professional look.

I dabbled in heels, blazers and the occasional sequin. I wore a dress to the Christmas party and never left the house without makeup on.

Like most good creatives, I have a couple side projects. One of which is a fashion and beauty blog. So you’d think I’d have a clue when it comes to clothes for work. Like the leggings-are-not-pants rule.

Instead, after years spent lounging around on recording studio couches, Fatboys in conference rooms and first-class flights to L.A., my somewhat stylish self started dressing for comfort. What did I need to wear heels for? Or silk shirts? Or any natural fabric at all, for that matter?

Everything went downhill after that.

Also, totally lied about that first-class flight to L.A. It was coach. And I wore leggings. As pants.

But leggings as pants were only the beginning.

Soon I stopped washing my hair and opted to keep my toque on all day at work (that’s Canadian for “hat”). And then there were legwarmers. Before legwarmers were cool again. Pretty soon, I was living in a hoodie. From high school.

That’s when I woke up. Something needed to be done. For the love of J.Crew! I had to get my shit together.

So I started the anti-schlep revolution. No more schlepping to work in something that could double as a cleaning-the-fridge outfit. And I made rules.

  1. Heels at least once a week. Even if they hurt or give me blisters. Style is pain.
  2. Do my hair. Every day. Headbands are a faux-pas.
  3. When in doubt, choose the pink one.

And I stuck to it. I was party-ready, at all times. Drinks after work at some chi-chi place? No problem. I’m dressed for it. Impromptu lunch meeting with someone important? Got it covered. My outfit is cute. Volunteer for that promotional in-house video? Of course. My cleavage is impressive today.

I’d like to report that I’ve kept at the anti-schlep revolution. And for the most part, I have succeeded. I suffer through whole days in heels and look like a gazelle walking home I them. I wear dresses and worry about it flying up and showing the world my underwear. But there are days when I just don’t want to wear pants. And those days are the hardest of all.




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