By EW his hair is waist-length and does get in his way, but he hasn't had a haircut since Coerthas and likely never will - see, the first half of FFXIV journal entry 11... (Incidentally there's another comic in the works about his hair, which I hope to complete soon)

Having just reached EW, the last major reason WoL cried was during the Faded Memories quest - here's the snippet of FFXIV journal entry 28 that shows as much.

FFXIV journal entry 32: Echo (1/2)

FFXIV journal entry 32: Echo (2/2)

The FFXIV playing card deck so far! As the poster boy WoL, Meteor is set to be one of the Jokers. But I keep thinking how fun it'd be to make custom decks where you can have your own WoL in there instead.......