The Englishman looks like he is going for a daring new look after posting pictures to Instagram.
On his personal page, he took two snaps that were uploaded to his story.
The first saw the ex-Leicester star sporting a barnet of straggly curls before his next picture showed off a more eyebrow-raising haircut.
In what might be best described as the Robert Doback look from Step Brothers, Drinkwater had shaved off the top of his head but left the sides.
"New look?" he captioned the picture, including several laughing emojis.
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While Drinkwater might have sported his fresh trim for a moment, it might be safe to say it did not hang around for long.
Instead, it appears that the midfielder is going clean-shaven, possibly preparing himself for a comeback to football.
The 33-year-old has been without a club for over a year now after his contract at Chelsea expired last summer.
Over five years at Stamford Bridge, he made just 23 appearances and just one after his debut campaign in 2017/18.
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After winning the Premier League with Leicester in 2016, he joined Chelsea for £35million a year after the club's grand success.
But he could never replicate the form that he showed at the King Power Stadium and was instead sent out on loan to various clubs including Aston Villa, Burnley and Kasimpasa in Turkey.
Off the pitch, Drinkwater has suffered several problems including being attacked outside a nightclub, headbutting a teammate and receiving a 20-month driving ban for drink-driving.
However, he is ready to put his troubled past behind him and find a new club.
Drinkwater said last week: "It's been a really good year. It felt nice to open up last year, I got good feedback about that.
"But since then, nothing's come up football wise that's really excited me. I was getting offers but nothing sat right at the time.
"If you go back two or three years, to the Chelsea scenario, I was in such a rut.
"I'm probably hungrier to play football now than I've been in years. This year out, it's helped me refresh and keep sharp mentally and physically. I've not wanted to play football this much since I was 16.
"I've missed the group environment, the banter, the routine. You can do a certain amount away from football but there's certain things you don't get."