Willkie Farr & Gallagher LLP, who advised Men’s Wearhouse on its recent acquisition of rival Jos. A. Bank passed on Armani and Zegna in favour of Joseph Abboud suits for $600, a once-prestigious brand now owned by Men’s Wearhouse. “If you’re going to make a pitch to a client for whom you’ll be charging a lot of money, you should know their product,” says Vice-chairman David Edwin.

Peter Comisar

Partner Steven Seidman says he wore a light blue number with a slight checkered pattern to multiple meetings over the six-month negotiation period since they were “custom-made.” Men’s Wearhouse’s directors

You need to dress to impress in mergers, acquisitions, and initial public offerings in the hypercompetitive world. It also helps to have a broad description of what that entails. Yoga, on the other hand, isn’t for everyone. One banker who pitched the idea recalls the elastic bottoms being too tight. “It was honestly rather embarrassing,” the banker adds, recalling leaving his hotel the morning of the pitch and feeling foolish as people in suits strolled by. Despite their determination to wear the pants, the bank was left out of the transaction.

Mr. Lubell recalls, “At the time,¬†Peter Comisar ¬†appeared in my newest Big T Cords, a wonderful shirt and blazer.” “In a sea of deep suits and ties, his style stood out.”

Even the banker remembers what he wore on that critical day: Olive green corduroy pants with white stitching around the pockets.The deal did not go through. Mr. Comisar, on the other hand, left such an impact on Mr. Lubell that he hired him to represent the brand in its sale to a private equity group years later.

Dressing up for a pitch has been a long-standing ritual. Gilbert Harrison, the founder of Financo LLC, a retail investment bank, recalls learning the lesson the hard way. Mr. Harrison wore his go-to shoe, black Gucci loafers, to a meeting with Interco Inc. in St. Louis in the 1970s. The number of wardrobe changes might quickly mount up. When it comes to selling luxury clientele, bankers are often required to pay for their suits and accessories, which can be costly.

Sartorial solicitation can be a tricky business at times. Ms. DeFlorio claims that she was typically the only woman in the room while working on Maidenform’s initial public offering. She recalls that if the management team or other bankers discussed the fit or comfort of the bras, they would motion to her and ask her opinion.

She admits, “It just killed me to buy them.” Worse yet, spending a lot of money didn’t help.

The business went with a different bank. Ms. DeFlorio recalls speaking to a room full of guys at a roadshow presentation in New York. She introduced Maidenform’s executive team with a veiled product advertisement that generated giggles to lighten the mood.

“I can attest to the excellence of this organization and its management team,” she continued, her hips thrust out for the punchline. “Most importantly, I can vouch for the product’s quality.”