Jon Hamm is leaning into his dad-era style, even as he admits he feels “terrified” about becoming a father in his mid-50s.
The 55-year-old actor was spotted running errands with his 38-year-old wife, actress Anna Osceola, at the upscale Gelson’s grocery store in Los Angeles on Sunday.
Hamm embraced a distinctly fatherly look, wearing an unbuttoned royal-blue shacket over a gray graphic T-shirt, dark gray shorts and slip-on sneakers.
He completed the casual outfit with a green dad hat and glasses, keeping his hands tucked into his pockets as he walked.
Osceola, meanwhile, displayed her growing bump in a white patterned midi dress paired with two-strap Birkenstock sandals.
She wore her strawberry-blonde hair loose and went makeup-free, adding oversized brown designer sunglasses to her relaxed look.
Jon Hamm is embracing his dad-era style after admitting he feels “terrified” about becoming a father in his mid-50s
The 55-year-old actor ran errands with his 38-year-old wife, actress Anna Osceola, at Gelson’s in Los Angeles on Sunday
Last month, Hamm addressed the couple’s baby news publicly, saying he was “very excited and deeply terrified” about welcoming a child with Osceola during an appearance on Late Night with Seth Meyers.
After host Seth Meyers, 52, displayed a photo of Hamm and Osceola at the Emmy Awards in early September, where her baby bump was visible, the Mad Men star enthusiastically confirmed: “We are having a baby!”
When Meyers asked whether he was looking forward to fatherhood, Hamm replied: “By turns very excited and deeply terrified. Yeah, so I think I’m doing it right.”
The pair also joked about becoming “old dads,” with Hamm poking fun at the considerable age difference between himself and his future child.
“When your kid is 70, you’ll be like, ‘I did it!’ When I’m 152,” he joked.
In August, Our News Outlet exclusively reported that Osceola was pregnant after she revealed her baby bump in a bikini during the couple’s vacation at a luxury resort in Ischia, Italy.
The pregnancy marked a dramatic shift for Hamm, who had previously said he did not “necessarily want kids.”
In a 2008 interview with The Guardian, while he was still dating longtime partner Jennifer Westfeldt, Hamm said: “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 recently said he was “very excited and deeply terrified” about welcoming a child with Osceola during an appearance on Late Night with Seth Meyers
Hamm and Osceola were seen in East Rutherford, New Jersey, in September
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Hamm and Osceola made their red-carpet debut in 2022 and later appeared together in the crime comedy film Confess, Fletch.
The couple’s engagement was confirmed in February 2023, prompting a source to discuss the next stage of their relationship with Us Weekly.
Hamm has also spoken about their romance on The Howard Stern Show, explaining that his relationship with Osceola prompted him to reconsider his views on love and family.
“I haven’t come down hardcore on either side of the argument. I think when people come from a stable family, having children becomes a celebration, and I’m not sure it would be that way for me.”
Before Osceola, Hamm was in a relationship with Westfeldt that began in 1997 and continued for nearly two decades before ending in 2015.
Hamm first met Osceola in 2015, when she appeared as a receptionist in an episode of the hit AMC series Mad Men. Just months later, Hamm and Westfeldt announced that they had ended their longtime relationship.
At the time, a source told the outlet that Hamm’s “party-heavy lifestyle” had become too much for Westfeldt. The source also claimed Westfeldt wanted him “to grow up,” while “he never wanted to.”
The Baby Driver actor was later photographed with Osceola in 2017, and the pair’s relationship was confirmed in 2020.
Osceola displayed her baby bump on the red carpet at the 2026 Emmy Awards in Los Angeles
Hamm met Osceola in 2015 when she played a receptionist in an episode of his hit AMC series Mad Men
Mad Men transformed Hamm’s life in several ways. The series launched his career and brought him widespread fame, but it also introduced him to the woman who would become his wife.
In 2010, while he was still with Westfeldt, Hamm said that neither he nor his girlfriend had any plans to marry.
“I don’t have the marriage chip, and neither of us have the greatest examples of marriages in our families,” he told Parade.
Although Hamm had previously ruled out walking down the aisle, he said in a 2022 interview with Sirius XM that his outlook changed after Osceola entered his life.
He credited Osceola with encouraging him to seek therapy for childhood trauma following his mother’s death—an experience that ultimately sparked a new desire to build a family.
Hamm said professional help “opened up the possibility of things like being married and having kids.”
In a June 2024 interview, Hamm said he hoped his marriage would eventually lead to children.
“It’s been great. And I hope it turns into kids. It’s not lost on me that I’m 53. I will be the old dad, but so it goes. It could be a good thing. We’ll see.”
