Scott McGillivray’s 10 Most Embarrassing Looks

I stand in solidarity with every pre-teen who’s had to show up to school with braces or headgear. Yes, it feels embarrassing, but now my teeth are perfectly straight, and the people who made fun of me are probably dealing with huge dental bills. At least, I like to think so.

Turtleneck sweaters and long wavy hair. It was a look. And I’m not ashamed.

I’ve been told I look like a young Fabio here, but I’m not sure how that comment was meant. I chalk the smooth, shiny hair up to a few VO5 hot oil treatments. But seriously, my hair is naturally wavy, so this look took some serious time in the morning.

You may remember that back in the late 90s, boy bands were kind of a big deal. Can you blame me for trying to look the part? I think I still have those silver pants somewhere…

Yeah… this one requires a bit of an explanation. I did not, I repeat DID NOT create this look for myself. I needed a few extra bucks and agreed to be a model for a hair show. I have some regrets.

I like to think of this as my “facial art” phase. It takes precision and determination to achieve a look like this, and there may have been one or two days where I had to walk around with Band-Aids on my face.

I don’t need glasses now, and I didn’t back then. But for a few days in 1998, I decided that pretending to have slightly impaired vision was super cool.

I think I looked pretty good! But any time people see this photo, they snicker and make an *NSYNC reference. Well *NSYNC just got a star on the Hollywood Walk of Fame, so who’s laughing now?!

When your hair can do this, you know it’s time for a cut. Sure, it worked for Bieber, but he was 12. It doesn’t work so well when you’re in your late 30s.

I’ve never looked worse!!!