Miss World America's Alissa Anderegg Marries Winthrop 'Win' Gruber in 'Timeless' Holiday Wedding in NYC (Exclusive) Erin ClackJanuary 27, 2026 at 4:26 AM 0 Winthrop "Win" Gruber and Alissa Anderegg Alex Logaiski for My Wedding Way Miss World America's Alissa Anderegg married Winthrop "Win" Gruber, the nephew of actor Kyle MacLachlan, in New York City on Jan. 3 The couple tells PEOPLE the elegant wedding was "a love letter to New York" Alissa and Win first met through a mutual friend in 2019 and got engaged in March 2024 For Alissa Anderegg and Winthrop "Win" Gruber, there's no place like home.
- - Miss World America's Alissa Anderegg Marries Winthrop 'Win' Gruber in 'Timeless' Holiday Wedding in NYC (Exclusive)
Erin ClackJanuary 27, 2026 at 4:26 AM
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Winthrop "Win" Gruber and Alissa Anderegg
Alex Logaiski for My Wedding Way
Miss World America's Alissa Anderegg married Winthrop "Win" Gruber, the nephew of actor Kyle MacLachlan, in New York City on Jan. 3
The couple tells PEOPLE the elegant wedding was "a love letter to New York"
Alissa and Win first met through a mutual friend in 2019 and got engaged in March 2024
For Alissa Anderegg and Winthrop "Win" Gruber, there's no place like home. That's why the couple decided to tie the knot with a glamorous New York wedding on Jan. 3, celebrating the romance and rich history of the iconic city.
Describing the nuptials as "a love letter to New York," the Miss World America 2020 winner, 31, tells PEOPLE the location was an obvious choice.
"New York is our home — and the place where our love story grew. It was only natural to celebrate here," she says, adding, "There was such a beautiful simiplicity in ending the night walking back home as husband and wife."
Alissa Anderegg and Winthrop "Win" Gruber
Alex Logaiski for My Wedding Way
The groom, who is the nephew of actor Kyle MacLachlan, was born and raised in the city. He and Alissa have since put down roots there together and co-founded Upper East Side Tan, a boutique tanning and red-light therapy studio that has four locations across New York and Miami.
Explaining her and Win's vision for their post-New Year's nuptials, Alissa says, "I wanted our wedding to feel timeless and deeply personal, and it meant so much to continue the holiday season with our loved ones by bringing them to the best city in the world."
Other top priorities? "Great food, great band, great company — and many nods to New York," Alissa shares. Those nods included a New York coffee table book that served as the guest book and the Frank Sinatra classic "New York, New York" for the cake-cutting.
Alissa Anderegg walks down the aisle
Alex Logaiski for My Wedding Way
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The wedding festivities kicked off with a welcome dinner on Jan. 2 at the couple's longtime favorite restaurant, Armani/Ristorante, featuring a custom menu curated by the bride and head chef Daniele Castellano.
After the dinner, the bridal party was "whisked away" to the Astor House, a neoclassical-style townhouse on the Upper East Side that was designed in 1927 by renowned architect Mott B. Schmidt for Vincent Astor. For the past 80 years, the landmark has served as the headquarters for the New York Junior League, of which Alissa is a member.
Winthrop "Win" Gruber and Alissa Anderegg
Alex Logaiski for My Wedding Way
The next day, Alissa and Win, 28, exchanged vows in a ceremony amid the towering grandeur of Saint Thomas Church, followed by a reception at one of the city's oldest private clubs. They were joined by 150 guests, including MacLachlan and his wife, producer Desiree Gruber; Milwaukee Brewers pitcher Trevor Megill, former NFL player Austin Mack and his wife, former Miss Missouri USA Joye Mack; and Win's godfather, Greek shipping magnate Peter Georgiopoulos, and his wife, model Kara Young.
The traditional ceremony was officiated by the couple's reverend, Father Mark Schultz. Alissa walked down the aisle in a princess-worthy Steven Khalil gown, paired with a royal-length veil of chantilly lace to complement the splendor of the church. For the reception, she added a "something borrowed" 19th-century diamond necklace from her bridesmaid, investor and haute couture collector Yu-Chi Lyra Kuo.
After Win and Alissa were officially declared husband and wife, they gathered with their guests for dinner and dancing to classic jazz standards, performed by the 11-piece Kevin Osborne band.
Winthrop "Win" Gruber and Alissa Anderegg
Alex Logaiski for My Wedding Way
The evening began with a cocktail hour featuring passed hors d'oeuvres and buffet stations, followed by a plated dinner. The menu included wild mushroom risotto, dry-aged ribeye, black sea bass and apple tart.
The couple also had a four-tier white chocolate wedding cake with fresh raspberry filling and delicate sugar flowers for decoration.
For their first dance, Alissa and Win chose "Can't Take My Eyes Off You." "It's a favorite oldie that all would recognize and love," the bride says.
Alissa Anderegg and Winthrop "Win" Gruber's wedding reception venue
Alex Logaiski for My Wedding Way
In a sentimental nod to the past, the pair displayed childhood photos throughout their reception. "Sourcing them from all our old family photo albums was especially meaningful. It was important for us to acknowledge our journey to where we are now and thank all of those who have supported us along the way," Alissa says.
MacLachlan's 17-year-old son, Callum, wore a couture tuxedo in the traditional MacLachlan family tartan. It was originally made for the Sex and the City actor by the late designer Vivienne Westwood. In a sweet full-circle moment, Win served as ring bearer in MacLachlan's 2002 wedding to wife Desiree.
From left: Desiree Gruber, Kyle MacLachlan, Alissa Anderegg, Winthrop "Win" Gruber and Callum McLachlan
Alex Logaiski for My Wedding Way
Alissa and Win's love story first began in 2019, when they were introduced by a mutual friend, influencer Jessica Bartlett. After a group trip to Miami, during which the pair immediately "hit it off," they began dating and eventually moved in together in New York.
Win popped the question to Alissa on March 26, 2024, on the balcony of their suite at the Faena hotel in Miami Beach.
Now that they are married, the two are looking forward to their next chapter together, including expanding their business.
Winthrop "Win" Gruber and Alissa Anderegg
Alex Logaiski for My Wedding Way
"We've already grown so much as a couple: being together nearly seven years, starting a business together and now getting married," Alissa notes. "We are an amazing team, and we're so excited to continue to grow together for the rest of our lives."
But first on the agenda, she says, is a honeymoon in "sunny" Anguilla.
Additional Credits:
Planner: Everything Fabulous for Your EventsBand: Hark Lane MusicFlorals: Ariston FlowersBridal gown shop: L'Fay BridalBridal makeup: Glow by Brenda LoweBridal hair: DarimaLighting: Sns StagingCandelabras: Regal Candelabra Rental
on People
Source: "AOL Entertainment"
Source: Entertainment
Published: January 26, 2026 at 10:36PM on Source: RED MAG
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