The New York fashion icon returns to the legendary Upper East Side cabaret November 23–28 with A Holiday Fruitcake, an irreverent celebration of music, comedy, and old-school Manhattan glamour.
There are few personalities who embody New York quite like Isaac Mizrahi. Designer, performer, storyteller, and unapologetic cultural provocateur, Mizrahi has spent more than three decades moving between fashion, theater, television, and music without ever feeling particularly obligated to choose just one.
And this November, he’s returning to one of the city’s most iconic stages to remind everyone that the holidays are infinitely more interesting with a little glamour, a great jazz band, and a healthy dose of mischief.
From November 23–28, Mizrahi brings A Holiday Fruitcake back to Café Carlyle, the legendary Upper East Side cabaret where sophisticated entertainment and quintessential New York eccentricity have shared a table for generations.
Accompanied by a six-piece jazz band led by pianist Ben Waltzer, Mizrahi promises an evening that refuses to behave like a conventional holiday concert. Expect seasonal favorites, unexpected musical interpretations, sharp cultural observations, and the kind of delightfully unpredictable storytelling that has made him as compelling behind a microphone as he is behind a fashion collection.
The musical references alone suggest that this won’t be your grandmother’s Christmas recital—unless, of course, your grandmother has impeccable taste and a particularly adventurous Spotify playlist. From the urbane sophistication of Noël Coward to the contemporary sensibilities of Billie Eilish, Mizrahi’s repertoire moves freely between generations and genres.
Part concert, part comedy show, and part intimate holiday gathering, A Holiday Fruitcake embraces the contradictions that have always defined Mizrahi’s creative identity: elegance and irreverence, sophistication and absurdity, nostalgia and experimentation.
A Fashion Icon Who Refuses to Stay in Fashion
Long before the term multihyphenate became a cultural cliché, Isaac Mizrahi was already living it.
His career has unfolded across some of the most recognizable institutions in American fashion and entertainment, from designing influential collections to hosting television programs, appearing on Broadway, and performing jazz standards in intimate cabaret rooms.
In 2022, he made his Broadway debut as Amos Hart in Chicago, adding another chapter to a career that has consistently challenged the boundaries between artistic disciplines.
His television work includes seven seasons hosting the Emmy Award-winning The Isaac Mizrahi Show and serving as a judge throughout all seven seasons of Project Runway All Stars.
But Mizrahi’s relationship with performance extends far beyond television. He has directed productions for the Opera Theatre of Saint Louis, designed costumes for the Metropolitan Opera, and annually directs and narrates Peter and the Wolf, a production originally created for New York City’s Guggenheim Museum.
Through his company, IM Entertainment, he continues developing projects across television, theater, publishing, and live entertainment. He also serves as Creative Director at Large for Target and is the author of the New York Times bestselling memoir I.M.
What connects these seemingly disparate pursuits is Mizrahi’s ability to turn personal perspective into performance. Whether discussing fashion, interpreting a song, or telling a story, his sensibility remains unmistakably his own.
The Enduring Charm of Unzipped
Mizrahi’s influence on contemporary fashion culture is perhaps most vividly captured in Unzipped, the cult-classic documentary he co-created and starred in.
The film, which celebrated its 30th anniversary in 2025 with a screening at the Sundance Film Festival, offers an intimate and often hilarious look at the creative anxieties, theatrical personalities, and backstage chaos surrounding the making of a fashion collection.
Recently re-released by Janus Films, Unzipped remains a reminder of a time when fashion was becoming increasingly intertwined with celebrity, media, and popular culture.
Three decades later, that intersection is practically the defining characteristic of the modern creative economy. Mizrahi, however, was exploring it long before it became an industry strategy.
And while the fashion world has changed considerably since the film’s original release, his combination of vulnerability, humor, and creative theatricality continues to feel remarkably contemporary.
A Holiday Party in One of New York’s Most Legendary Rooms
Of course, a show like A Holiday Fruitcake deserves a setting with as much personality as its headliner.
Originally opened in 1955, Café Carlyle has long represented a particular vision of New York nightlife: intimate, elegant, musically sophisticated, and just eccentric enough to remain interesting.
Over the decades, its stage has welcomed performers ranging from Elaine Stritch and Eartha Kitt to Debbie Harry, Alan Cumming, Jon Batiste, and Jeff Goldblum.
For 36 years, the venue was famously associated with cabaret legend Bobby Short, whose performances helped establish its reputation as one of Manhattan’s most distinguished musical institutions.
With seating for approximately 90 guests, music-themed murals by Oscar-winning French artist Marcel Vertès, and an atmosphere that feels suspended somewhere between old Hollywood and classic New York society, Café Carlyle offers something increasingly rare: the opportunity to experience a major cultural personality in a genuinely intimate setting.
Located inside The Carlyle, A Rosewood Hotel, the venue is part of a Manhattan landmark that has stood at Madison Avenue and East 76th Street since 1930.
The hotel’s Art Deco heritage, its connection to New York’s artistic community, and its proximity to Central Park have helped preserve an atmosphere of timeless Upper East Side glamour.
For Mizrahi, whose work has always balanced a reverence for classic sophistication with a mischievous desire to disrupt it, the setting feels particularly appropriate.
The Holidays, According to Isaac
There is something refreshing about an artist who refuses to treat elegance and humor as mutually exclusive.
At a moment when so much entertainment is designed to fit neatly into categories, Mizrahi continues to make a compelling case for creative unpredictability.
His performances draw on the traditions of cabaret, jazz, comedy, and theatrical storytelling without surrendering the spontaneous personality that has defined his public life.
And perhaps that’s what makes A Holiday Fruitcake such an appealing proposition: the promise of a holiday celebration that doesn’t take itself too seriously, even when the musicianship is exceptional.
After all, if anyone can make a Billie Eilish song coexist with Noël Coward in an Upper East Side cabaret, it’s probably Isaac Mizrahi.
This November, New York gets another opportunity to experience the city through his wonderfully unconventional lens.
And for one week, at least, the holidays might be a little more fabulous.
Event Details
Isaac Mizrahi — A Holiday Fruitcake
Dates: November 23–28, 2026 (no performance on Thanksgiving, November 26; confirm individual performance dates and times)
Venue: Café Carlyle, The Carlyle, A Rosewood Hotel
Address: 35 East 76th Street, New York, NY
Music: Six-piece jazz band led by pianist Ben Waltzer
Tickets: Café Carlyle reservations via Tock
More information: HelloIsaac.com
Instagram: @IMISAACMIZRAHI | @CafeCarlyle
