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Old Nokias and other pre-smartphone era phones did.

My Bose QC 35 headphones have a 2.5mm socket but on the headphones end for when you'd want to use them wired. It came with a cable with a 3.5mm male plug for the source device and the 2.5mm male plug on the side that goes to the headphones.

Never seen a wired headset with 2.5mm male plug that goes to the source device however.

Not headsets, but Bose ANC headphones have used a 2.5mm jacks for years (and still do). They give you a 2.5 to 3.5mm cable, though. I imagine this is likely just to drive cable sales, though, as there isn’t any real reason you need the 2.5mm jack on their relatively big headphones.

I had an HTC Wizard (branded by T-Mobile) many year ago, which had a 2.5mm jack.

I have the Cingular version and had forgotten this detail. Sure enough, you’re right- it has a 2.5mm jack on it. How unusual.

I think some portable minidisc players and discmans around 2000 used 2.5mm.