"Great night with @chelseahandler AND her new haircut!! #girlfriends," Jenner, 58, captioned the picture.
Handler debuted her new look online on Dec. 3 with the cheeky caption, "The best head in town." The look is reminiscent of Handler's real-life bestie Jennifer Aniston, who recently chopped off her locks into a similar bob. (Aniston's mini-makeover was courtesy of longtime hairstylist Chris McMillan.)
The Kardashian-Jenner clan matriarch has visited Handler's show several times recently, and even did a Chelsea Lately "take over" when Handler was out back in March 2013, filling in for the candid host.
And though they seem to have an amicable relationship, Handler, 38, has no problem bashing the reality family frequently on her show. But all reports of a feud between the two have been quashed publicly by Handler herself.
After Star Magazine reported that Handler told Jenner to "shut her pie hole," at an E! executive's house after the mother of six supposedly made a disparaging comment about President Obama, Handler brought up the rumors on her show in September 2013.
"This story is ridiculous," Handler joked. "I've never even been to an E! executive's house, except for the one I slept with to get this job."