• by Sarah Mahoney , Staff Writer @mahoney_sarah, March 26, 2025

Men’s Wearhouse, long a go-to source for workwear and wedding gear, knows that between back-to-office mandates and Zoom-call casual, many guys are just plain confused. Its latest campaign -- “What Do I Wear to This Thing?” -- aims to help.

Created with agency Party Land, the campaign leans into humor, reminding customers that advice and options are as close as their nearest Men’s Wearhouse. Matt Repicky, senior vice president and chief brands officer at Tailored Brands, explains what the company hopes to achieve.

Interview edited for length and clarity.

Retail Insider: Tell us about the campaign.

Matt Repicky: We wanted to show people we’ve got answers for all kinds of “what should I wear?” challenges -- like his sister’s 40th birthday with a dress code, the annual neighborhood BBQ hosted by his judge-y married couple friends, and an inhumanely hot outdoor wedding.

Retail Insider: Is a key goal moving people from brand awareness to consideration?

Repicky: Yes. Everybody knows Men’s Wearhouse. We benefit from mentions on everything from "SNL" to Marvel movies -- we’re already in the zeitgeist.

Our strategy is about creating mass reconsideration. We’re reintroducing Men’s Wearhouse to people who think they already know us, making the brand feel more relevant than ever, while staying true to what’s always made us great.

We’re convinced humor is the way to do that. Last year’s campaign, also from Party Land, drove a double-digit increase in awareness and a significant increase in consideration. Oracle’s research, for example, finds that 90% of people are more likely to remember funny ads, and 72% say they’d choose a humorous brand.

Guys aren’t supermodels. They just want to look good without having to think too hard. And as the return-to-office trend picks up, raising more what-to-wear questions, we tried to get in front of men as they make some of those decisions.

Retail Insider: Yet none of the new spots show men in offices. Why?

Repicky: One of the insights behind this work is that people know us as a place to buy a suit or rent a tuxedo. Thanks to all those ads by George Zimmer, the founder, people know we sell tailored clothing. But they don't always track that we have more casual offerings -- things like polo shirts, chinos, or jeans.

As you think about returning to work, you may or may not be wearing a suit. It’s a new environment, and you have questions. We want to show that we have helpful, knowledgeable consultants in our stores to make that easier for you.

Suits still exist -- we still sell a lot of them. But we are not just suits.

Retail Insider: Is this especially confusing for Gen Z? Or is it more about the office/casual, suit/no-suit dilemma? Once upon a time, magazines like GQ and Esquire spelled out the rules. Who’s in charge now?

Repicky: I don't know. Social media has provided a platform, and Gen Z especially uses it for fashion questions. They trust creators and influencers more than fashion experts.

I don’t see this as strictly generational -- though Gen X may have more experience wearing suits. I’d say it’s more persona-based.

We work with Morning Consult as our brand insights partner, and we go into the field every week to talk with 300 guys about menswear, including our brand. That gives us great nuggets. People don’t dress up as they used to, but there are still case-based situations. Maybe I’m usually more casual, but this week, I’m giving a presentation to the CEO.

Retail Insider: Not to get political, but confusion seems everywhere. President Donald J. Trump recently mocked Ukraine President Volodymyr Zelenskyy for not wearing a suit to the Oval Office, and the internet erupted -- billionaire Elon Musk never wears suits there either. Do even those guys know the rules? Or are there simply no rules anymore?

Repicky: I'm not saying there aren't any rules -- just that there's not a singular place people turn to. It's unfettered, and there are a lot of voices.

Collectively, they say, “Here’s a direction you might go in.” But there’s no singular source of truth anymore.

Retail Insider: Speaking of Musk -- can you talk about the tech industry's influence on menswear? From Steve Jobs’ black turtleneck to those cliché Patagonia vests, is Silicon Valley still driving the office-casual look?

Repicky: That probably depends on your role at the company. Again, there are no universal truths here.

I live in the Bay Area, and I know plenty of tech folks looking to level up their style. The shift toward casualness continues, but nothing is as uniform as it used to be. It’s not like the days when your choices were a black, navy, or grey suit.

It’s more up in the air, and that causes some consternation. Since it’s not prewritten, you have to think harder about what you’ll be doing that day.

Retail Insider: For younger men, especially, beloved brands are the opposite of workwear: Vuori, Lululemon, and Nike. They’re wearing sweatpants everywhere. How does that impact you?

Repicky: We certainly carry those types of products. I love wearing them, too.

Comfort underlies that trend, and we live in a world where people want everything to feel as good as joggers. That evolution means men are more interested in -- and open to -- fabric technology. We’ve seen it in athletic wear and expect it in all clothes.

The wedding spot, for example, focuses on a suit made with Chillflex, a temperature-controlled fabric we’re using in many of our suits. People are loving it.

Retail Insider: How big is this campaign?

Repicky: It’s significant. Men’s Wearhouse is the biggest brand in our portfolio, and this is a multichannel campaign. We’re using TV, YouTube, streaming platforms, and plenty of social -- we know that’s where people go first for advice.