• by Erin Everhart , Staff Writer, February 14, 2025

I’ve seen a lot of ads. I’ve heard a lot of jingles. As a proud elder millennial, we had to wait until 9pm on Thursdays to watch our favorite TV shows, and it was during those times, we (gasp!) couldn’t fast forward through commercials. This idea of skipping ads just didn’t exit; if you didn’t want to watch commercials, you watched a movie.

And I don’t remember all of them, but there are a few commercials, a few campaigns, a few taglines that are so deeply rooted in my memory, it’s like they were a part of my childhood.

Reb Bull gives you wings. Finger lickin’ good. Maybe she’s born with it; maybe it’s Maybelline. I’m lovin’ it. A diamond is forever. And…I guarantee it. You’re going to like the way you look; I guarantee it. 

To this day, I can still vividly recall George Zimmer saying those words at the end of every Men’s Wearhouse commercial: the suits he was wearing, the infliction in his voice, the slight curve of his smile.

When a brand is so intrinsically tied to its tagline, how (and when) do you decide it’s time for a change? And how do you bring a newer generation along, showing them you’re not just the place where your dad buys his suits?

After 49 years, Men’s Wearhouse decided it was time. This week, I sat down with Tailored Brands Chief Brands Officer Matt Repicky to hear how they’re building reconsideration to the next generation of shoppers with their latest brand, “Love the Way You Look.” You can listen t the entire podcast at this link.