Party Land’s New Spots Find the Humor in Everyday Style Dilemmas

If and when guys think about fashion, it can be a little stressful, as men tend not to be too confident when it comes to clothing choices. Which is why humor—defusing that tension—makes a lot of sense for the category.

We see this in Party Land’s work for Men’s Wearhouse. The retailer embraced humor in a campaign last year that introduced the “Love the Way You Look” platform (a line taken from the old Men’s Wearhouse ads with George Zimmer). Now, it’s back with three more spots, which tap into the truth that guys just want to know what to wear and where to get it.

The ads star Chris Kleckner, a Groundlings improv actor, who has to figure out what to wear to his sister’s birthday party, a neighborhood barbecue, and a summer wedding. In each case, he nails it—thanks to the products and service at Men’s Wearhouse.

Directed by Peter Martin, the spots feature other improv actors in supporting roles, including Greg Cromer, Katie Walder, and Beth Dover.

“Comedy works because it makes people feel seen,” said Matt Heath, co-founder and chief creative officer at Party Land. “Most fashion ads love to pretend every guy is a supermodel, but most guys just want to look good without having to think too hard.” The humor, he said, makes the brand “feel more relevant and more like the guys who shop there.”

“Our strategy is all about creating mass reconsideration, and there’s no better way to do that than with comedy,” said Matt Repicky, chief brands officer at Tailored Brands. “We’re reintroducing Men’s Wearhouse to people who think they already know us—making the brand feel more relevant than ever while still staying true to what’s always made us great.”

Last year’s campaign drove a double-digit increase in awareness and a significant increase in consideration, the brand said. The new spots will air nationwide this spring across broadcast, connected TV, social, and digital platforms.

This article appeared in AdAge, written by Tim Nudd on March 26, 2025.