Jon Hamm, 50, dons tiny shorts with bikini-clad Anna Osceola, 33, snorkeling in Mediterranean Sea

He is best known for his role as sharp-dressing, smooth talking advertising creative director Don Draper in Mad Men.

But Jon Hamm stripped down to a much different suit on his latest outing.

The 50-year-old actor donned a pair of tiny swim shorts while enjoying a recent snorkeling outing in the Mediterranean Sea with his much younger girlfriend Anna Osceola, 33.

Scroll down for video 

Making a splash: Jon Hamm, 50, donned a pair of tiny swim shorts while enjoying a recent snorkeling outing in the Mediterranean Sea with his much younger girlfriend Anna Osceola, 33

The two were certainly primed for some fun in the sun as they were seen on a boat just off of the Italian island of Pantelleria.

Jon kept it comfortable in the yellow, green, and orange patterned shorts which he paired with a white long-sleeved button-down shirt and baseball cap.

Anna donned a multi-colored vertical striped mini dress before stripping to her patterned bikini.

Chill: The two were certainly primed for some fun in the sun as they were seen on a boat just off of the Italian island of Pantelleria

Relaxing: Jon kept it comfortable in the yellow, green, and orange patterned shorts which he paired with a white long-sleeved button-down shirt and baseball cap

Vibes: He washed up before wrapping a towel around his shoulders

Stunning: Anna showed off her fab figure in a two-piece bikini

Her red tresses were worn down as they flowed like waves over her shoulder as she showed off her natural looks by going make-up free. 

The two enjoyed some time aboard the yacht before getting into their swimwear and jumping into the sea.

The couple sweetly swam side-by-side as they explored the water on the romantic outing. 

Though the pair are relatively private when it comes to their relationship, they first met on the set of Mad Men and appeared in the series finale together. 

Pretty: Her red tresses were worn down as they flowed like waves over her shoulder as she showed off her natural looks by going make-up free

Cute: The couple sweetly swam side-by-side as they explored the water on the romantic outing

One with the ocean: Jon took his snorkel and goggles off to dip his head in the ocean

Just us: It seemed to be quite the fun day

Cuddling close: The happy couple were seemingly inseperable

Found each other: Anna and Jon’s relationship seemed to be a slow burn as they had been spotted leaving a coffee shop together in 2017 before they were seen a year later playing tennis

Things only turned romantic during the quarantine, five years after he split from longtime partner Jennifer Westfeldt in 2015. 

 In June they were seen attending the premiere of his film No Sudden Move at the Tribeca Festival. 

And Anna and Jon’s relationship seemed to be a slow burn as they had been spotted leaving a coffee shop together in 2017 before they were seen a year later playing tennis. 

Perfect: Anna donned a multi-colored vertical striped mini dress over her patterned bikini

They have since proved to maintain a close bond as they spent California’s COVID-19 lockdown together.  

In between that time he had also been linked to Ben Affleck’s producer ex Lindsay Shookus, after they were glimpsed at a touchy-feely dinner.   

But his rep told Page Six that they had ‘not dated [and] are not friends,’ continuing to call them mere ‘acquaintances.’  

Remember when: The flame-haired actress appeared on the Mad Men finale back in 2015 (pictured) and was first linked to Jon over the summer of last year