As a kid, Halloween was all about getting free candy, as a 20-something it was an excuse to have a party and now as a dad with young kids, it’s all about getting free candy again! (Just kidding, I would never steal my kids’ candy!). But sweets aside, I’ve always gotten a kick out of dressing up in costumes for Halloween – and over the years I’ve had some pretty impressive ones (and some pretty embarrassing ones). Take a walk down memory lane with me, as I relive the good, the bad and the downright horrifying costumes of Halloweens past!
Scott McGillivray is a real estate expert and host of HGTV Canada’s Income Property and Moving the McGillivrays.
Published October 2, 2017, Updated October 20, 2019
Editor’s note: we’re (summer) lovin’ this look of Scott dressed up as Danny Zuko from Grease on The Marilyn Denis Show in 2018. You’ll want to check out this video of Scott reacting to the photos from this gallery.
Editor’s note: also from 2018, this snap of Scott and his family has him channelling some serious hippie vibes. “Peace out,” he captioned on Instagram.
Related: From Thanksgiving to Halloween: Fall Decor for Under $100
Editor’s note: in 2017, Scott and his wife Sabrina dressed up for a Halloween party as some pretty awesome pirates. “We ARrrrrrr having fun tonight,” he joked on Instagram.
The Walking Dad
Halloween is one of my favourite times of the year because I get to live out some of my craziest fantasies. I’ve always wanted to be an extra on The Walking Dead and I think this is as close as I’m ever going to get!
Master of the Universe
Back in 1999 I decided to channel my inner He-Man. I admit that my quads might need a little extra work, but otherwise I think the resemblance is uncanny.
When you’re working on Halloween as a lifeguard, you’re a little limited for costume options. I can’t remember who came up with the Conehead theme, but it was a genius idea. It’s the Halloween equivalent of a swim cap. (Of course, looking back, an injured lifeguard seems a little counterintuitive).
Related: Do You Dare? 13 Haunted Houses From Horror Movies You Can Visit in Real Life
It Takes a Village
I’m not going to say it was the best Village People costume ever, but once a construction worker, always a construction worker. Even when you’re the evening’s entertainment, it’s important to stay on brand. You can quote me on that.
Baby’s First Halloween
Halloweens haven’t been the same since this little one came into mine and Sabrina’s lives. It may have been pretty different from previous years, but Myah’s first Halloween was probably my favourite.
Scott’s Pumpkin Pride
My competitive side definitely comes out at Halloween. Now not only do I need to have the best costume, but I feel like I need to carve the best pumpkin! When Myah and Layla’s friends come trick or treating I want them (and their parents) to be blown away. I was pretty happy with this one, but I’m going to try to up my game this year.
Related: The Most Over-the-Top Decorated Homes for Halloween
McGillivray Family Fun
The family that plays together, stays together and we definitely like to play together. Sabrina is the best at making costumes and decorating the house and she really goes all out at Halloween. But to be honest, sometimes I think Layla’s just humouring us.
A Real Head Scratcher
When you find a giant zombie head with glowing eyes in a homeowner’s basement, what other choice do you have but to try it on for size? I wouldn’t recommend trying this at home though. Renovating while wearing a skull bobblehead is something best left to the professionals.
Sometimes the people around you inspire the best Halloween costumes. So cheers to Mike Holmes whose hair game has always been strong. Thanks for always giving me something to aspire to, buddy!
Good Cop, Bad Cop
I never thought I’d be the kind of guy to do a couples costume, but come on, how awesome is this? Truth be told, Sabrina doesn’t need to dress up like a police officer for me to do whatever she tells me. But I’m glad she did!
Dad on Duty
Other than the last day of school, there’s no day that’s more fun to take the kids to school than Halloween. They’re so excited to be in their costumes, you can’t help but be excited with them. And no princess ever looked as cute as Myah in her car seat. (Don’t worry, we were parked in the driveway when we took the selfie!).
Ken Stole My Look
Remember that year I accidentally went as the new Ken doll? Or did he go as me? They say imitation is the sincerest form of flattery, but I take issue with the receding hairline and dad bod.
Beware the Hair
A boy bander’s evil twin? A castoff from The Lost Boys? I’m afraid not. The scariest thing about this picture is that it wasn’t even for Halloween. This, ladies and gentlemen, is what hair shows looked like in the late ’90s and early 2000s. But come October 31st, I might need to recreate this look.
Interview With the Vampire
I didn’t intend to make myself look like an extra from an Anne Rice book, but I’m really channeling my inner Lestat here. Who says you need a costume when a little makeup and a photo app will do?
Hanging With My Pumpkins
Best Halloween moment ever? Going to the pumpkin patch with my girls to choose the perfect pumpkin. We started the year Myah was born and now it’s a yearly tradition. Even though I’ve been known to grow my own pumpkins in the garden, we still make it a family event. It wouldn’t be fall without it!
Related: 15 Holiday Traditions Scott McGillivray Never Misses
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