![Jon Hamm soaks in the summer-like weather in tiny shorts and flip-flops during food run to a market | Daily Mail Online Jon Hamm soaks in the summer-like weather in tiny shorts and flip-flops during food run to a market | Daily Mail Online](https://i.dailymail.co.uk/1s/2021/03/29/05/41063144-9413271-image-m-3_1616992323479.jpg)
Jon Hamm soaks in the summer-like weather in tiny shorts and flip-flops during food run to a market | Daily Mail Online
![Jon Hamm gets close to a redheaded female friend as they pickup takeout amid coronavirus shutdown | Daily Mail Online Jon Hamm gets close to a redheaded female friend as they pickup takeout amid coronavirus shutdown | Daily Mail Online](https://i.dailymail.co.uk/1s/2020/03/22/02/26254882-0-image-a-86_1584845711271.jpg)
Jon Hamm gets close to a redheaded female friend as they pickup takeout amid coronavirus shutdown | Daily Mail Online
![Jon Hamm goes casual in plain white t-shirt as he social distances in line to pick up lunch in LA | Daily Mail Online Jon Hamm goes casual in plain white t-shirt as he social distances in line to pick up lunch in LA | Daily Mail Online](https://i.dailymail.co.uk/1s/2020/05/17/00/28480462-8327199-image-m-51_1589672932103.jpg)
Jon Hamm goes casual in plain white t-shirt as he social distances in line to pick up lunch in LA | Daily Mail Online
![Jon Hamm soaks in the summer-like weather in tiny shorts and flip-flops during food run to a market | Daily Mail Online Jon Hamm soaks in the summer-like weather in tiny shorts and flip-flops during food run to a market | Daily Mail Online](https://i.dailymail.co.uk/1s/2021/03/29/06/41064654-0-image-a-14_1616996157386.jpg)
Jon Hamm soaks in the summer-like weather in tiny shorts and flip-flops during food run to a market | Daily Mail Online
![Jon Hamm and Anna Osceola pack on the PDA as they enjoy Mediterranean Sea on holiday in Pantelleria | Daily Mail Online Jon Hamm and Anna Osceola pack on the PDA as they enjoy Mediterranean Sea on holiday in Pantelleria | Daily Mail Online](https://i.dailymail.co.uk/1s/2021/09/04/18/47506237-9958029-On_vacation_Jon_Hamm_50_and_his_girlfriend_Anna_Osceola_33_looke-a-1_1630775126083.jpg)
Jon Hamm and Anna Osceola pack on the PDA as they enjoy Mediterranean Sea on holiday in Pantelleria | Daily Mail Online
![Jon Hamm and Casey Affleck pull off casual chic as they arrive at a pre-Grammys party in Los Angeles | Daily Mail Online Jon Hamm and Casey Affleck pull off casual chic as they arrive at a pre-Grammys party in Los Angeles | Daily Mail Online](https://i.dailymail.co.uk/1s/2022/04/02/22/56140567-0-image-m-11_1648936485934.jpg)
Jon Hamm and Casey Affleck pull off casual chic as they arrive at a pre-Grammys party in Los Angeles | Daily Mail Online
![Jon Hamm, 50, puts toned legs on display in tiny shorts while out with girlfriend Anna Osceola, 32 | Daily Mail Online Jon Hamm, 50, puts toned legs on display in tiny shorts while out with girlfriend Anna Osceola, 32 | Daily Mail Online](https://i.dailymail.co.uk/1s/2021/03/13/16/40421680-9358617-image-m-5_1615654673191.jpg)
Jon Hamm, 50, puts toned legs on display in tiny shorts while out with girlfriend Anna Osceola, 32 | Daily Mail Online
![Jon Hamm is spotted kissing Jane Lynch instead of his new 'girlfriend' Lindsay Shookus | Daily Mail Online Jon Hamm is spotted kissing Jane Lynch instead of his new 'girlfriend' Lindsay Shookus | Daily Mail Online](https://i.dailymail.co.uk/1s/2019/09/23/17/18655548-7494761-Jon_Hamm_seen_here_before_the_show_over_the_weekend-a-1_1569255392184.jpg)
Jon Hamm is spotted kissing Jane Lynch instead of his new 'girlfriend' Lindsay Shookus | Daily Mail Online
![Jon Hamm gets close to a redheaded female friend as they pickup takeout amid coronavirus shutdown | Daily Mail Online Jon Hamm gets close to a redheaded female friend as they pickup takeout amid coronavirus shutdown | Daily Mail Online](https://i.dailymail.co.uk/1s/2020/03/22/02/26254878-0-image-a-97_1584845754810.jpg)
Jon Hamm gets close to a redheaded female friend as they pickup takeout amid coronavirus shutdown | Daily Mail Online
![Jon Hamm, 49, and Mad Men co-star girlfriend Anna Osceola, 32, enjoy a beach day in Santa Barbara | Daily Mail Online Jon Hamm, 49, and Mad Men co-star girlfriend Anna Osceola, 32, enjoy a beach day in Santa Barbara | Daily Mail Online](https://i.dailymail.co.uk/1s/2020/09/28/20/33733326-0-image-a-1_1601322494943.jpg)
Jon Hamm, 49, and Mad Men co-star girlfriend Anna Osceola, 32, enjoy a beach day in Santa Barbara | Daily Mail Online
![Jon Hamm is a silver fox with stubble as he models tiny shorts while walking dog Splash | Daily Mail Online Jon Hamm is a silver fox with stubble as he models tiny shorts while walking dog Splash | Daily Mail Online](https://i.dailymail.co.uk/1s/2021/03/26/20/40991468-9407969-image-m-166_1616791413901.jpg)
Jon Hamm is a silver fox with stubble as he models tiny shorts while walking dog Splash | Daily Mail Online
![Jon Hamm enjoys solo stroll through LA's quiet streets as COVID-19 crisis forces city into lockdown | Daily Mail Online Jon Hamm enjoys solo stroll through LA's quiet streets as COVID-19 crisis forces city into lockdown | Daily Mail Online](https://i.dailymail.co.uk/1s/2020/03/20/10/26201370-8134169-image-a-12_1584700560824.jpg)
Jon Hamm enjoys solo stroll through LA's quiet streets as COVID-19 crisis forces city into lockdown | Daily Mail Online
![Jon Hamm gets close to a redheaded female friend as they pickup takeout amid coronavirus shutdown | Daily Mail Online Jon Hamm gets close to a redheaded female friend as they pickup takeout amid coronavirus shutdown | Daily Mail Online](https://i.dailymail.co.uk/1s/2020/03/22/02/26254884-0-image-a-88_1584845723907.jpg)
Jon Hamm gets close to a redheaded female friend as they pickup takeout amid coronavirus shutdown | Daily Mail Online
![Jon Hamm pays tribute to Saturday Night Live with his gray hoodie while on a grocery run in LA | Daily Mail Online Jon Hamm pays tribute to Saturday Night Live with his gray hoodie while on a grocery run in LA | Daily Mail Online](https://i.dailymail.co.uk/1s/2020/12/14/23/36845104-9053483-image-a-2_1607989361365.jpg)
Jon Hamm pays tribute to Saturday Night Live with his gray hoodie while on a grocery run in LA | Daily Mail Online
![Jon Hamm, 51, and his girlfriend Anna Osceola, 34, enjoy sunny stroll with Sarah Silverman in NYC | Daily Mail Online Jon Hamm, 51, and his girlfriend Anna Osceola, 34, enjoy sunny stroll with Sarah Silverman in NYC | Daily Mail Online](https://i.dailymail.co.uk/1s/2022/05/22/19/58143025-0-image-a-40_1653243253706.jpg)
Jon Hamm, 51, and his girlfriend Anna Osceola, 34, enjoy sunny stroll with Sarah Silverman in NYC | Daily Mail Online
![Madly in love! Jon Hamm and girlfriend Jennifer Westfeldt walk hand-in-hand in New York | Modest purple dress, Jon hamm, Celebrity look Madly in love! Jon Hamm and girlfriend Jennifer Westfeldt walk hand-in-hand in New York | Modest purple dress, Jon hamm, Celebrity look](https://i.pinimg.com/originals/2f/21/41/2f2141ac4ad5d779af9a0e13dbf32485.jpg)
Madly in love! Jon Hamm and girlfriend Jennifer Westfeldt walk hand-in-hand in New York | Modest purple dress, Jon hamm, Celebrity look
![Jon Hamm is a silver fox with stubble as he models tiny shorts while walking dog Splash | Daily Mail Online Jon Hamm is a silver fox with stubble as he models tiny shorts while walking dog Splash | Daily Mail Online](https://i.dailymail.co.uk/1s/2021/03/26/20/40992684-0-image-a-165_1616791395532.jpg)
Jon Hamm is a silver fox with stubble as he models tiny shorts while walking dog Splash | Daily Mail Online
![Jon Hamm enjoys the sunny Los Angeles weather in a set of shorts and sandals while walking his dog | Daily Mail Online Jon Hamm enjoys the sunny Los Angeles weather in a set of shorts and sandals while walking his dog | Daily Mail Online](https://i.dailymail.co.uk/1s/2021/04/02/16/41266610-9430679-Doing_his_thing_Jon_Hamm_was_spotted_taking_in_the_bright_spring-a-14_1617378993442.jpg)
Jon Hamm enjoys the sunny Los Angeles weather in a set of shorts and sandals while walking his dog | Daily Mail Online
![Jon Hamm steps out on a grocery run wearing a mask and bandana over part of his face | Daily Mail Online Jon Hamm steps out on a grocery run wearing a mask and bandana over part of his face | Daily Mail Online](https://i.dailymail.co.uk/1s/2020/12/13/04/36777774-9047857-image-m-81_1607833647222.jpg)
Jon Hamm steps out on a grocery run wearing a mask and bandana over part of his face | Daily Mail Online
![Jon Hamm and Casey Affleck pull off casual chic as they arrive at a pre-Grammys party in Los Angeles | Daily Mail Online Jon Hamm and Casey Affleck pull off casual chic as they arrive at a pre-Grammys party in Los Angeles | Daily Mail Online](https://i.dailymail.co.uk/1s/2022/04/02/23/56141477-0-image-a-31_1648939729307.jpg)
Jon Hamm and Casey Affleck pull off casual chic as they arrive at a pre-Grammys party in Los Angeles | Daily Mail Online
![Jon Hamm rocks sweater made famous by The Big Lebowski's The Dude while shopping in Hollywood | Daily Mail Online Jon Hamm rocks sweater made famous by The Big Lebowski's The Dude while shopping in Hollywood | Daily Mail Online](https://i.dailymail.co.uk/1s/2022/06/06/23/58762329-0-image-a-48_1654554023524.jpg)
Jon Hamm rocks sweater made famous by The Big Lebowski's The Dude while shopping in Hollywood | Daily Mail Online
![Jon Hamm steps out on a grocery run wearing a mask and bandana over part of his face | Daily Mail Online Jon Hamm steps out on a grocery run wearing a mask and bandana over part of his face | Daily Mail Online](https://i.dailymail.co.uk/1s/2020/12/13/05/36778734-9047857-image-m-86_1607837087409.jpg)
Jon Hamm steps out on a grocery run wearing a mask and bandana over part of his face | Daily Mail Online
![Jon Hamm proves to be the ultimate gentleman as he STOPS traffic for girlfriend Anna Osceola in NYC | Daily Mail Online Jon Hamm proves to be the ultimate gentleman as he STOPS traffic for girlfriend Anna Osceola in NYC | Daily Mail Online](https://i.dailymail.co.uk/1s/2021/06/19/06/44414875-9703201-image-m-168_1624079437071.jpg)
Jon Hamm proves to be the ultimate gentleman as he STOPS traffic for girlfriend Anna Osceola in NYC | Daily Mail Online
![Jon Hamm steps out on a grocery run wearing a mask and bandana over part of his face | Daily Mail Online Jon Hamm steps out on a grocery run wearing a mask and bandana over part of his face | Daily Mail Online](https://i.dailymail.co.uk/1s/2020/12/13/05/36779260-0-image-a-9_1607838696164.jpg)