As the owner of one of Calgary’s top boutique event-planning companies, Derek MacDonald knows how to dress for the occasion

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Dress for the Occasion: Derek MacDonald on Vintage Style

One year into his fine arts degree at the Alberta College of Art + Design, Derek MacDonald needed to pick a major. At the same time, his friend, Nathan Redekopp, suggested they go into business together.

“I had all this tuition money, and I thought: okay, I could stay in school, that’s one really formal way to get an education,” MacDonald laughs. “Or … I can just take this adventure and see what happens.”

Jumping headfirst into the more-daring option, MacDonald funnelled his tuition money into building his first business, Junk Star Vintage, a vintage clothing store on 17th Avenue S.W. “I’m so glad I made that choice,” he says. “Going into that business taught me way more than I ever would have bargained for.”

After a few years at Junk Star, during which he travelled around Canada bringing vintage steals back home to Calgary, he moved on to event planning at e=mc2. But he knew he needed to be his own boss. In 2011, he launched Boom Goes the Drum, a full-service special event-planning boutique. After only two years in the business, he won the ISES Esprit Award for best social event budget over $75,000 for the Paul Hardy Design 10th anniversary celebration fashion show.

Although he may have a tendency to keep a keen eye on the next big adventure, MacDonald is also a man of patient awareness, in his work and in his style. He won’t settle on anything before it’s a perfect fit, be it a venue, a band or a denim jacket, which makes his wardrobe one to be reckoned with. After years of collecting vintage clothes and waiting for the right item to come along, MacDonald has refined a definitive, timeless look that keeps getting better with age

Leather coat and sweatshirt are vintage; shoes by Converse; jeans by J Brand from Holt Renfrew; belt from American Apparel.

What was it like to throw yourself into building a business from scratch?

I had learned a lot about what to focus on from starting my first business, but it’s still hard. You have to have that mentality where you put a lot of years and a lot of hard work into something before you start to see payoff. There are times I work 90 hours a week, but I still love it so much and I have so much support that it makes it a pleasure to go through the challenges.

What were the deciding factors in choosing to take the plunge into business?

It was an adventure; I’m a sucker for a big idea and an adventure. It was staring me right in the face, and, as adventurous as art history class is, I never really wanted to do the “safe” thing. Not knowing the final outcome is kind of what excites me, just to see what happens.

Trench by Calvin Klein; jacket from Scotch & Soda; pants by J. Lindberg; tuxedo bib by Paul Hardy; belt from Coach; tie and loafers are vintage.

What is it about vintage clothing that attracts you?

Growing up, I used to shop at the Salvation Army in High River. They had these sales where you could fill up a Safeway shopping bag full of vintage for $5. I would go and find these great bell-bottoms and polyester shirts. I was always picking vintage. I fell in love with the fact that it was hard to find — it’s not like when you go to the mall and find the perfect fit and colour in every size. 

Do you still stick to vintage?

I have more of a classic style now. I’ve stopped wearing vintage T-shirts and blue jeans; I used to wear that every day. Now I’m all about vintage shoes. If I can find vintage shoes, I’m in love.

So what sort of clothes are you drawn to these days? 

I’m more into a pared-down, classic look. Everything has to have function before form. I stick to pretty basic clothes, building off of these pieces, but I’m not flashy at all. Maybe it’s from when I was 14 years old and being heckled for wearing striped bell-bottoms through the streets of High River, but I’m a little more conservative in what I wear now. I’m much more about the way that things fit and the purpose that they serve, rather than if they grab attention.

Sweater by Paul Hardy; shirt from J.Crew; jeans by J Brand from Holt Renfrew; boots from Gravity Pope.

Would you say a lot of your clothing is an investment? 

I view my closet as a collection now. For me, it’s more about finding something that fits just perfectly, and then keeping it and wearing it every fall or every winter. 

And has the collection stood the test of time? 

I’m really into mending things. I have the greatest seamstress in the whole world. She’ll be able to mend pieces that I’ve had for years and, if it starts to feel like it doesn’t fit right, she’ll take it in or out. I like that feeling, knowing that the shirt that I’ve had for four years will feel like new again with just a little bit of a tweak. 

Trench coat by Moon from Hudson’s Bay; blazer from H&M; pants from Levi’s; shirt by Ralph Lauren; bag by Filson from Hanson’s Fishing Outfitters; shoes and tie are vintage; umbrella from London Drugs.

I take it you don’t put much stock in trends? 

No, I feel like I’m wearing an outfit that I would have worn when I was 16. My jeans are probably a little bit more expensive and I would have had holes in my shirt back then, but I’ve seen so many things come and go — patterns and col-ours — I just like classic things. I like to feel like I’m wearing something that I could have worn when I was 16 and I could possibly be wearing when I’m 50. I don’t want something that’s just in the moment. You need to feel comfortable in what you’re wearing, because, when you see somebody wearing something just because it’s trendy right now, it screams off of them.

Jacket from Scotch & Soda; pants by J. Lindberg; belt from Coach; pocket square from Brooks Brothers; toe and loafers are vintage.

You’re a perfectionist with your style, aren’t you? 

That’s funny — you’re the second person to call me a perfectionist in the past hour. But I guess you’re right. In my head, I’m always thinking that it’s all about the nuance and subtlety — but I think you’re bang-on there.

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