Miss World America 2020 Alissa Anderegg and Winthrop ‘Win’ Gruber, nephew of actor Kyle MacLachlan, tied the knot in a sophisticated, heartfelt New York City wedding on January 3rd, celebrating their love story with a “love letter to New York.”
In a celebration that felt both grand and intimately personal, Miss World America 2020 Alissa Anderegg married Winthrop “Win” Gruber in a dazzling New York City wedding on January 3rd. The couple, who have built a life and business together in the city, chose to make their nuptials a “love letter to New York,” blending iconic locations, elegant traditions, and meaningful personal touches into a truly unforgettable event.
The festivities began on January 2nd with a welcome dinner at the couple’s favorite spot, Armani/Ristorante, featuring a custom menu curated by Alissa and head chef Daniele Castellano. The bridal party then enjoyed a pre-wedding gathering at the Astor House, a historic neoclassical townhouse on the Upper East Side and the headquarters for the New York Junior League, of which Alissa is a member.
The following day, the couple exchanged vows in the stunning grandeur of Saint Thomas Church, a setting that perfectly matched the princess-worthy elegance of Alissa’s Steven Khalil gown and her royal-length Chantilly lace veil. The ceremony was officiated by the couple’s reverend, Father Mark Schultz, and was followed by a reception at one of the city’s most exclusive private clubs, attended by 150 guests.
Photo Credit: Alex Logaiski for My Wedding Way
The reception was a masterclass in refined celebration, featuring a plated dinner with wild mushroom risotto, dry-aged ribeye, and black sea bass, all accompanied by classic jazz standards from the 11-piece Kevin Osborne band. The culinary highlight was a four-tier white chocolate wedding cake with fresh raspberry filling, which the couple cut to the sounds of Frank Sinatra‘s “New York, New York.” For their first dance, Alissa and Win chose the timeless “Can’t Take My Eyes Off You.”
Guests were treated to numerous personal and family details. The couple displayed childhood photos from family albums, a sentimental nod to their journey together. Alissa accessorized her reception look with a “something borrowed” 19th-century diamond necklace from her bridesmaid, Yu-Chi Lyra Kuo. In a touching full-circle moment, Kyle MacLachlan‘s 17-year-old son, Callum, wore a couture tuxedo in the family’s traditional tartan—a garment originally made for MacLachlan by the late designer Vivienne Westwood. Win had previously served as ring bearer in MacLachlan’s 2002 wedding.
Photo Credit: Alex Logaiski for My Wedding Way
Their love story began in 2019 when they were introduced by a mutual friend. After a group trip to Miami where they “hit it off,” they began dating and eventually moved in together in New York. Win proposed to Alissa on March 26, 2024, on the balcony of their suite at the Faena hotel in Miami Beach.
Alissa and Win are not just partners in life but also in business. They co-founded Upper East Side Tan, a boutique tanning and red-light therapy studio with four locations across New York and Miami. “We’ve already grown so much as a couple: being together nearly seven years, starting a business together and now getting married,” Alissa shared. “We are an amazing team, and we’re so excited to continue to grow together for the rest of our lives.”
Photo Credit: Alex Logaiski for My Wedding Way
As they begin their new chapter, the couple is looking forward to a honeymoon in “sunny” Anguilla. Their wedding stands as a testament to a love that is both deeply rooted in the city they call home and ready to embrace the future together.
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