Miss World America 2020 winner Alissa Anderegg and her longtime partner Winthrop “Win” Gruber tied the knot in a glamorous New York ceremony on Jan. 3. The couple celebrated their love in a setting they called a “love letter to New York,” and the wedding drew 150 guests, including actor Kyle MacLachlan and former MLB pitcher Trevor Megill. Their union marks a new chapter for both their personal lives and their shared business, Upper East Side Tan.
At a Glance
- Miss World America 2020 winner Alissa Anderegg married Winthrop “Win” Gruber in New York on Jan. 3.
- The ceremony, described as a “love letter to New York,” hosted 150 guests.
- The couple co-owned Upper East Side Tan and plans to expand the business.
Why it matters: The wedding blends celebrity culture with entrepreneurial ambition, showcasing how personal milestones can elevate a brand.
Love Story and Engagement
Alissa and Win first met in 2019 through a mutual friend, influencer Jessica Bartlett. After a group trip to Miami where they “hit it off,” they began dating and eventually moved in together in New York. Win popped the question on March 26, 2024, on the balcony of their suite at the Faena hotel in Miami Beach.
Wedding Planning and Venue
The festivities kicked off with a welcome dinner on Jan. 2 at the couple’s favorite restaurant, Armani/Ristorante, featuring a custom menu curated by head chef Daniele Castellano. After dinner, the bridal party was whisked to the Astor House, a neoclassical townhouse on the Upper East Side that was designed in 1927 by architect Mott B. Schmidt for Vincent Astor. For 80 years the landmark served as the headquarters of the New York Junior League, of which Alissa is a member.
On Jan. 3, Alissa and Win exchanged vows in Saint Thomas Church, a historic venue on the Upper East Side, followed by a reception at one of the city’s oldest private clubs. The ceremony was officiated by Father Mark Schultz, the couple’s reverend.
Reception Highlights
Alissa walked down the aisle in a princess-worthy Steven Khalil gown paired with a royal-length veil of chantilly lace. She added a “something borrowed” 19th-century diamond necklace from bridesmaid Yu-Chi Lyra Kuo to her look. After the vows, the couple served dinner and dancing to classic jazz standards performed by an 11-piece Kevin Osborne band.
The menu included:
| Course | Dish |
|---|---|
| Appetizer | Wild mushroom risotto |
| Main | Dry-aged ribeye, black sea bass |
| Dessert | Apple tart |
They also featured a four-tier white chocolate wedding cake with fresh raspberry filling and delicate sugar flowers. For their first dance, Alissa and Win chose “Can’t Take My Eyes Off You,” a favorite oldie that everyone could recognize.
Family and Friends
The guest list included notable figures such as actor Kyle MacLachlan, his wife Desiree Gruber, former MLB pitcher Trevor Megill, former NFL player Austin Mack and his wife Joye Mack, and Greek shipping magnate Peter Georgiopoulos with model Kara Young. MacLachlan’s 17-year-old son Callum wore a couture tuxedo in the traditional MacLachlan family tartan, a piece originally made for the actor by designer Vivienne Westwood. In a sweet full-circle moment, Win served as ring bearer in MacLachlan’s 2002 wedding to Desiree.
Future Plans
Alissa and Win look forward to expanding Upper East Side Tan, which currently has 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 said. “We are an amazing team, and we’re so excited to continue to grow together for the rest of our lives.” Their next agenda item is a honeymoon in “sunny” Anguilla.
Credits
- Planner: Everything Fabulous for Your Events
- Band: Hark Lane Music
- Florals: Ariston Flowers
- Bridal gown shop: L’Fay Bridal
- Bridal makeup: Glow by Brenda Lowe
- Bridal hair: Darima
- Lighting: Sns Staging
- Candelabras: Regal Candelabra Rental
