Can Hugo Boss Actually Be Cool?

“You could hike a mountain in this,” Mr. Greider proclaimed, saying sales of suits for the brand recovered last summer, in tandem with scaled-back lockdown measures across the world. “People wanted to get dressed up and go to restaurants.”

(The “suit of tomorrow” will arrive in stores in “late January.”)

There are still some classic Hugo Boss elements amid these new clothes, to be sure: European tailoring, preppy, billowy button-downs. (Mr. Grieder does not want to alienate the brand’s existing customers, who may find the new look somewhat startling.) But there are some forward-looking elements, too. One standout comes from the Boss line, in the form of an oversized long-sleeve button-down and shorts set, available in an on-trend burnt orange. And women’s lounge shorts have the voluminous proportions of basketball shorts, flirting with androgyny.

Why is Mr. Greider so convinced this is the way forward? Because, he said, he had a secret weapon: Gen Zers themselves.

Throughout the overhaul, Boss hired teenagers to work as consultants and assist on photo shoots. “Gen Zers are a rare commodity,” said Miah Sullivan, who oversees marketing and communications at Boss and is herself a millennial — though perhaps what is more true is that Gen Zers who want to engage with big brand executives on the subject of suiting are a rare commodity.

“I go to this Gen Z consultant — he has an agency, he’s 17, and a complete boss — and he gives me advice on how to execute, how to augment, how to change,” Ms. Sullivan said.

Sometimes the consultant, whom Ms. Sullivan declined to name, also helped the brand find other consultants.

“It’s actually hard to find Gen Z on LinkedIn,” said Ms. Sullivan. “They’re on TikTok.”

Whether they will also be in Boss while on TikTok is now the hope — and the question.