Jon Hamm Embraces 'Dad Fashion' Amidst Anticipation of First Child

Jon Hamm, 55, was recently spotted embracing a "dad style" during an errand run in Los Angeles with his pregnant wife, Anna Osceola, 38. The actor donned a royal blue shacket over a graphic t-shirt, paired with grey shorts and slip-on sneakers, accessorized with a green dad hat and eyeglasses. Osceola, meanwhile, showcased her baby bump in a white patterned midi dress and sandals.

This public appearance comes after Hamm spoke about his impending fatherhood in an interview on Late Night with Seth Meyers. He described the experience as "very excited and deeply terrified," acknowledging the unique challenges of becoming a parent in his mid-fifties. He humorously noted the age gap with his future child, joking, "When your kid is 70, you'll be like, 'I did it!' When I'm 152."

The couple's pregnancy news was first exclusively reported in August, with Osceola debuting her baby bump during a vacation in Italy. This development marked a shift for Hamm, who had previously expressed reservations about having children. In a 2008 interview, he stated, "I don't necessarily want kids. A lot of our friends are having children and I don't know if it's for me."

Hamm and Osceola, who made their red carpet debut in 2022, also appeared together in the crime comedy "Confess, Fletch." They became engaged in February 2023. Hamm has spoken about how his relationship with Osceola inspired him to seek therapy for childhood trauma, which in turn opened his mind to the possibility of marriage and starting a family. He previously credited her with inspiring him to reevaluate his love life.

Hamm first met Osceola in 2015 when she guest-starred on an episode of his acclaimed AMC series, Mad Men. Shortly after, Hamm and his long-term partner Jennifer Westfeldt announced their separation. At the time, sources suggested Hamm's lifestyle was a contributing factor, with Westfeldt reportedly wanting him to "grow up." The actor and Osceola were first seen together in 2017 and confirmed to be dating in 2020.

In a 2010 interview, Hamm stated he and Westfeldt had "no interest in tying the knot," citing a lack of positive marriage examples in their families. However, he later revealed in a 2022 interview that his perspective changed after meeting Osceola, particularly after undergoing therapy that helped him address childhood issues, including the death of his mother. This therapeutic journey, he explained, "opened up the possibility of things like being married and having kids."