Jon Hamm and Anna Osceola’s Red Carpet Love Story: From Mad Men to Wedding Glamour

Hollywood heartthrob Jon Hamm is officially off the market — he’s now a married man!

Wedding Details: Anna Osceola’s A-Line Gown and Hamm’s Classic Tuxedo

The Mad Men star married Anna Osceola on June 24, 2023, at Anderson Canyon in Big Sur, California — the exact iconic location where the final episode of Mad Men was filmed. Born in 1988, Osceola is 17 years younger than Hamm, born in 1971.

Celebrity guests at the intimate ceremony included Billy Crudup, Paul Rudd, and Tina Fey. Osceola walked down the aisle wearing a strapless, A-line wedding gown, while Hamm looked dapper in a black tuxedo.

Jon Hamm and Anna Osceola turned heads at the ESPY Awards, with Hamm in a sharp black tuxedo and Osceola stunning in a black floral gown paired with a red clutch (Credit: Xavier Collin / ABACA / INSTARimages / Cover Images)

Red Carpet Glamour: Anna Osceola’s Metallic Heels at Vanity Fair 2025

Continuing their red carpet streak, Jon Hamm and Anna Osceola made a glamorous appearance at the 2025 Vanity Fair Oscar Party, once again showcasing their effortlessly sophisticated style.

Jon Hamm looked sharp in a classic black tuxedo and patent leather dress shoes, while Anna Osceola dazzled in a shimmering, figure-hugging metallic gown paired with strappy metallic stiletto sandals that elongated her statuesque frame on March 2, 2025, in Beverly Hills, California (Credit: Doug Peters / PA Images / INSTARimages)

Anna Osceola’s metallic stiletto sandals, paired with a soft pink pedicure, perfectly elongated her legs and complemented her shimmering gown

Mad Men Beginnings: How Jon Hamm and Anna Osceola’s Love Story Started

Although they’ve mostly kept their relationship out of the spotlight, it’s believed they first met on the set of Mad Men, where Osceola appeared in a small but memorable role in the final episode.

In the episode, the actress played the front desk clerk at Esalen, a spiritual retreat in California that Hamm’s character, Don Draper, visited.

Jon Hamm’s Don Draper meets Anna Osceola’s Esalen receptionist in Mad Men’s final episode, where their on-screen encounter later blossomed into real-life romance (Credit: AMC)

Hamm was in a long-term relationship with Jennifer Westfeldt then, but split from his partner several months after 18 years of being together in 2015.

The couple had expressed a desire to avoid marriage numerous times before the breakup.

“I don’t have the marriage chip, and neither of us have the greatest examples of marriage in our families. But Jen is the love of my life, and we’ve already been together four times longer than my parents were married,” Hamm told Parade in 2014.

In September 2015, Jon Hamm and Jennifer Westfeldt ended their relationship after being together for 18 years (Credit: INFphoto)

Couples Style: Elevated Footwear Moments on the Red Carpet

Osceola was first photographed with the Curb Your Enthusiasm actor in 2017, and they were romantically linked in 2020. Since then, they’ve been out and about together, enjoying meals, playing tennis, and vacationing in Italy in September 2021.

They made their red carpet debut at an Oscars afterparty in March 2022 and have attended several other events together since then.

Height & Shoe Size: How Anna Osceola and Jon Hamm Compare in Heels

Standing at 5 feet 11 inches (1.80 meters), Anna Osceola is nearly as tall as her husband, Jon Hamm, who measures 6 feet ¾ inch (184.8 cm). When she wears high heels, their height difference virtually disappears on the red carpet. Osceola wears a US women’s shoe size 9, while Hamm wears a US men’s shoe size 11.5.

Jon Hamm and Anna Osceola attend the Top Gun: Maverick premiere in San Diego, with Hamm in a sleek black suit and Osceola elongating her 5’11” frame in neon yellow ankle-strap stiletto sandals paired with a striped mini dress (Credit: Fayes Vision / Startraksphoto)

In May 2022, they were spotted on the red carpet at Sarah Silverman’s musical Bedwetter. In July, they participated in the 2022 ESPY Awards, and in September, they attended a screening of their film Confess, Fletch.

In a 2022 interview with Howard Stern, Hamm shared that his relationship with Osceola felt “settled and comfortable,” opening him up to the idea of marriage and starting a family.

Reflecting on his personal growth, Hamm noted that working through past trauma had made his current relationship even more meaningful, allowing him to envision “a new version of happiness, life, [and] wellness.”

Jon Hamm and Anna Osceola made their first public appearance as a couple at Vanity Fair’s Oscars Party on March 27, 2022, at the Four Seasons Hotel in Los Angeles, with Hamm in a textured velvet tuxedo jacket and Osceola turning heads in a high-slit geometric gown paired with strappy black stiletto sandals (Credit: PA Images / INSTARimages)

The couple appeared together in Confess, Fletch, where Hamm starred as journalist Irwin M. Fletcher, with Osceola playing a supporting role. Before meeting Hamm on Mad Men, Osceola had guest roles on shows like Saving Grace, Greek, Rizzoli & Isles, NCIS, and Law & Order.

The actor and his wife don’t use social media and keep their personal affairs private. In 2017, Hamm told InStyle, “The point of life is not to put dog ears on yourself and post it online for everyone to see.”