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Suiting Up for ‘The Wolf of Wall Street’: A Chat With One of Cinema’s Most Sought-After Tailors

The Wolf of Wall Street Interview Leonard Losdail
Paramount Pictures

“These are left over from the strippers,” says an extra adding a pile of crinkled white button-downs to the wardrobe station, its tables already drizzled with majorette hats, plastic tubs full of men’s brown, leather wingtips, and standalone racks of fully styled outfits. With some actors having participated in a bathroom brawl scene the night before and an airplane orgy earlier still, dozens of women with classic ‘Working Girl’-style hair poofs and men fitted in their stockbroker best begin lining up for a final approval before heading to the bullpen set, where they’d soon be bombarding Leonardo DiCaprio’s Jordan Belfort with job requests.

And despite all these distractions on the set of ‘The Wolf of Wall Street,’ these background actors made time to approach one man dressed in a classic, pinstriped suit to ask, “Is this the Leonard Logsdail?”

“I’m surprised all the time that I’ve got to where I am,” remarks Logsdail on the generous attention he receives, though it’s well warranted. Aside from his thriving made-to-measure and bespoke tailoring services, based out of his New York showroom in Midtown Manhattan, Logsdail’s suiting work already popped up in a slew of films, such as Robert De Niro’s ‘The Good Shepherd,’ Oliver Stone’s ‘Wall Street,’ Ridley Scott’s ‘American Gangster,’ Ron Howard’s ‘Frost/Nixon’ and, of course, ‘The Wolf of Wall Street.’

In Martin Scorsese’s latest, based on the memoir of Jordan Belfort, DiCaprio portrays this true-to-life, corrupt stockbroker in all his hard-partying, cocaine-snorting, quaalude-popping, sex-addicted lifestyle in the late ’80s and early ’90s. As he goes from hawking penny stocks to setting up his own brokerage firm, Stratton Oakmont, targeting the wealthiest 1% of Americans, he earns himself the nickname “The Wolf of Wall Street.” But first, he must look the part.

“They only call me in for the big stars,” says Logsdail, the foremost reason being that he denounces all ego, having developed a tough skin through working with difficult (though, in some cases, that’s a generous term) customers in his day-to-day work life. “I don’t care if they have a hissing fit. I can really concentrate on what I need to do and get my work done. I have no ego in it; I’m happy to do whatever the actor and the costume designer says.”

Consulting with three-time Oscar-winning costume designer Sandy Powell – who worked on a number of Scorsese films, winning her second Academy Award for ‘The Aviator’ — on the film, Logsdail developed a variety of suits for DiCaprio, Ethan Suplee (playing one of Belfort’s original associates), Jon Favreau (Belfort’s lawyer), Rob Reiner (Belfort’s father) and Matthew McConaughey (Belfort’s first boss in the stockbroker business). Flaring trousers and shapely blazers quickly became more fitted as the film’s timeline progressed over, Logsdail approximates, its 10-year span.

“The lapels changed, a little bit narrow or wider; the shoulders changed a little bit, a little bit more shape; a little bit shorter jacket,” he describes. “Sandy’s very into the subtle nuances of an era that make the difference that when somebody looks at it they may not even notice the difference there.”

In addition to Logsdail, Powell enlisted longtime friend of DiCaprio and Scorsese collaborator Giorgio Armani for the outing, and was able to dip into his vast archives. “The era of power dressing on Wall Street projected tremendous amounts of resolute strength,” she previously said of the effort. “We endeavored to capture that iconic look through our partnership with Mr. Armani.”

Armani’s relationship with DiCaprio proved itself fruitful in the past, though not for Logsdail. As he recollects, “I started ‘The Great Gatsby.’ I did the pilot and DiCaprio walked in and said, ‘Who’s this?’ And [the producers] said, ‘Oh, this is Leonard. He’s the tailor. He’s going to make your clothes.’ [DiCaprio replied,] ‘Oh, we don’t need him. Armani will make my clothes for nothing.’” In the end, Brooks Bros. became the primary clothing partnership.

The Wolf of Wall Street Matthew McConaughey
Paramount Pictures

Luckily, Logsdail got his chance to work with DiCaprio for ‘The Wolf of Wall Street’ — although he also previously produced suits for the Scorsese-DiCaprio ‘Shutter Island,’ they were for Ben Kingsley — and he proved himself through his ability to get inside the characters’ heads. “I often believe 90% of our business is psychology and 10% is tailoring,” he says. ”Sometimes the costume designer and the actor and I will sit here, and I will listen to their to and fro as they’re beginning to create the image they want to put onto the screen. And I have to understand that because they’re not gonna go in the back and make that.”

Getting into character comes naturally to the tailor, who also appears with his son, Leonard, Jr., in ‘The Wolf of Wall Street,’ playing a tailor, no less. “I got the call from David Davenport, who’s a great guy, who was first assistant to the costume designer [Sandy Powell]. He said, ‘We need two tailors. Do you wanna be one of them?’ So I did one, and my son actually came on and did the second one.”

Logsdail, Sr. had the opportunity to play an extra twice before – working with De Niro, whom he praised for boosting his own confidence, in ‘The Good Shepherd,’ and with Oliver Stone in ‘Wall Street,’ which he called one of the more fun experiences – but his presence on the set of ‘The Wolf of Wall Street’ and witnessing the theatrical hustle and bustle behind the scenes made him appreciate all those involved in making the wardrobe process move as smoothly as possible, especially for scenes with so many moving parts.

“There was a guy across the hallway who had a snake around his neck,” he describes of the chaos. “Apparently this actually happened on the trading stocks floor of this Jordan Belfort. There was a gerbil, a hedgehog, a parrot and a snake, and … they brought in a monkey on rollerblades.”

As a tailor working in Manhattan during the ‘90s, Logsdail recalled many encounters with these real-life Wall Street stockbroker types and their off-the-cuff shenanigans. “They were under so much pressure. That’s why they started drinking, that’s why they started doing drugs; the pressure to keep going all the time was tremendous. And so they did these wacky things to goof off from the stress.

He continues, “We had this tailor’s chalk, and I would sharpen it into a glass so that when people came in I did fittings to mark the suits. The amount of these Wall Street guys that came in and said two things: ‘Can I have a line?’ ‘cause they thought it was cocaine, and the other one, ‘Don’t leave that when you go ‘cause the help will steal it.’”

Logsdail has a lifetime’s worth of these wild tales of the trade, having been keeping a running tab since he first conceived his business three months after his 21st birthday. In his early days as a tailor working in London, he remembers how one of his first “horrible” jobs was to mop the mice droppings off the suits hanging in the hovel out of which he worked above Carnaby Street. “I had nothing to fall back on. I had to make it work.”

Soon he set his sights on America, with which he fell in love on his first trip. Each visit lasted about two weeks, during which time he’d visit clients and expand his business. He would eventually marry an American and fully move over with his wife, child (and one on the way) and four suitcases of belongings. “I used to work and work and work, and chase any order anywhere, and nearly went out of business,” he says. “In fact, I started writing letters to clients telling them I [couldn't] make [their suits].”

With no money in the bank, two children and a mortgage, Logsdail was scraping along, until a surprising savior turned things around — one of his more “difficult” customers. Keeping the man’s name to himself, Logsdail was on the verge of denying him service in order to maximize his more profitable orders. After finally succumbing, however, this unlikely customer ordered three suits and paid 50% up front, which Logsdail then used to turn his business around. “I always had a soft spot for him. He was always difficult, always a pain in the neck, and I just put up with him because to me he was like a little guardian angel that came along just when I needed him.

“I told this guy a number of years later, and it’s like he couldn’t care less,” he says, though no doubt Logsdail will always remember that moment, especially when upcoming films on which he’s worked — like ‘Winter’s Tale‘ with Colin Farrell and Russell Crowe, and the new Joel Kinnaman-led ‘RoboCop‘ remake — hit theaters. With ‘The Wolf of Wall Street,’ however, he sees his fashions slipping more into the shadows of the casts’ powerhouse performances.

“I’m not sure this movie is going to become any type of style leader,” he speculates, with films like James Bond and ‘The Great Gatsby’ in mind. “You never know. Look what happened to ‘Wall Street’ 1 with the horizontal and the suspenders … I think people are going to be more taken up with the action they will with the clothes, if I’m being honest.”

‘The Wolf of Wall Street’ is now playing in theaters.

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