From tefillin to tailoring: the Chabad Savile Row-trained couturier

Yosel Tiefenbrun is hands down the most unusual rabbi you will ever encounter. To begin with, he doesn’t dress in the typical black and white associated with the strictly Orthodox. Colour is his thing — from occasional denim on his rare days off, to his striking, almost waist-length red beard, a look that is part Rembrandt portrait, part Jewish ZZ Top.

Yosel Tiefenbrun, 36, is a master tailor, based in New York’s Tribeca district. His path to his showroom (he has another, where he started, in Brooklyn) is a riotous journey that takes in a batmitzvah in Singapore, an artist grandfather and his own beginnings as the eldest of a family of 10, raised in the Chabad tradition.

But overshadowing all of this is Yosel’s training — which took place in London’s Savile Row. He jokes that “being a Lubavitch kid running around Golders Green and asking people if they were Jewish” had given him a perfect grounding for knocking on doors in Savile Row and being turned away — until he wasn’t.

The near-nomadic life of Chabad families — charged by the late Lubavitcher Rebbe, Menachem Schneerson, with bringing the love of Judaism to all parts of the world — applied equally in Yosel’s case. He was born in New York but raised in London, where his father served as a chazan. Creativity runs in the family, he thinks. His grandfather was indeed an artist — one of his portraits of the Rebbe is on display in Yosel’s tailoring studio — but it was his grandmother who was the inspiration. “She was really artistic — she made beautiful pieces of art with dried leaves, she knitted and crocheted… she brought home paint and told him, ‘Why don’t you give it a try?’” Not that the Tiefenbrun children were able to watch their grandfather painting. “It was a very private pursuit and he would be totally absorbed in the work – usually portraits of famous rabbis.”

From the age of about nine or 10, the future tailor “really started paying attention to what I was wearing”. He took care of his clothes and admits that he was “fussy” about ensuring things matched, and that he “pushed the boundaries” when it came to which shoes or coloured socks (not regulation white) to wear to yeshiva. But, says Yosel with a smile, “I played it well. I knew where the limits were and I didn’t get into trouble.” The opposition came not so much from his parents – although he concedes they were anxious about the example he was setting for his younger siblings – but more from his school or yeshiva.

Aged 18, he was at summer camp in California and, knowing he wanted to work in fashion and design, was questioning whether to go back to yeshiva in New York. “But my parents persuaded me to return, and I did. But at the same time I was also sketching….” The sketches, incidentally, were for women’s fashion.

That year was “very important”, recalls Yosel, as the Chabad shlichut — emissary — element took hold. He and several other young men were sent to Singapore to work for the movement, although he had no intention of becoming a rabbi.

“Singapore shaped my future — the two years I spent there were among the greatest in my life,” he says. He qualified as a rabbi there and also studied interior design, but a fortuitous meeting with the fashion editor of Harper’s Bazaar at a batmitzvah got him an internship at the magazine.

Somewhat to his surprise, Yosel discovered that he rather liked being a rabbi — “I liked talking to people, helping them, learning with them.” So he faced a dilemma: “How do I make this work?” He considered applying to Central Saint Martins in London, but lacked the qualifications. Having avidly watched fashion shows in Singapore, he decided instead to follow Alexander McQueen’s path — bringing Savile Row tailoring into the design of womenswear.

Yosel’s determination to bestride both the world of the rabbinate and the world of fashion eventually led him to knocking on doors in Savile Row. Everyone turned him away, so he tried studying tailoring at Newham College. But it was frustrating: “You can’t learn tailoring in a group of 25 students.” So it was back to knocking on Savile Row doors. This time he caught the attention of Trinidadian-born Andrew Ramroop, head of the Maurice Sedwell Academy, who had faced similar struggles breaking into Savile Row. Recognising Yosel’s drive, Ramroop took him on as an apprentice to master every aspect of world-class tailoring.

In London, Yosel spent hours in vintage shops, buying old suits and jackets to dismantle back at Savile Row — studying how great tailors achieved perfect balance and drape. (He even deconstructed a vintage Brioni suit he later wore to his engagement party.) He also encountered the age-old dilemma for observant Jewish tailors — shatnes, the ban on mixing wool and linen. Its reason is unknown, but the rule must be obeyed. Rabbis told Yosel it was permissible to make shatnes-containing garments for non-Jews. Yet while he once created shatnes-free suits only for Jewish clients in New York, today none of his tailoring includes the forbidden blend.

Before New York, he and his wife Chaya spent two more years in Singapore working with the Jewish community. True to form, Yosel split his time between rabbinical duties and interning with top tailor Kevin Seah — and although he’d considered women’s fashion, he soon fell in love with men’s tailoring.He enjoys the challenge — a very Yosel word — of making a suit that drapes and flatters even the most imperfect figure. He now employs four tailors and Chaya runs the accounting and management side of the business. The couple have three children.

“I’m a full-time tailor who happens to be a rabbi,” Yosel says now, but adds with a grin that the rabbi part is so ingrained that it comes out when he deals with clients. Certainly you are unlikely to find any other tailor who has both a bar in his studio and a set of tefillin, should a client suddenly feel compelled to take part in this mitzvah. “I had a pair of tefillin made specially for the shop — and they are used pretty often.” Yosel admits to sometimes being taken aback at the willingness of even secular Jews to agree to lay tefillin. “Look, they know who I am. They’re not walking into a synagogue here, but I am openly religious and I always try to talk to the man and get to know him. It’s in my blood, and I am proud of it and I want to share.

“I was making a wedding suit for one gentleman; I never had the guts to ask him if he would like to lay tefillin. The wedding was in Berlin. The Uber was outside the studio and he had a suit bag in his hand and was ready to leave. He had his hand on the door and I asked him, would you like to put on tefillin? And he said, ‘Absolutely, I would love to.’ That taught me I shouldn’t wait till the last moment.”

Now thriving after six years in New York, Yosel finds his early ambition to design for women returning. It began when he replicated a client’s wife’s coat pattern; next may come exquisitely-tailored women’s suits — or even evening wear. Meanwhile, as he forges an international reputation, people fly in from around the world for a unique experience — a bespoke suit, made to measure by a rabbi, thus ensuring the hechsher (certificate of approval), and tefillin if desired.