NYS drivers licenses went digital over 15 years ago, so every time one renews* they use the same picture. So, for lots of people, their pictures on dl won't match how they look today--so far, I've had no problem with TSA.
[Eventually people will request new pictures.]
*NYS DMV (to save money) tries to have everyone do transactions by mail or the internet (since lines at the DMV generally are very long.
)
A TDC at Logan gave me a hard time about my NYS DL once, not because of the photo (which was pre-beard) but our licenses have a security weave as opposed to a hollogram. Eventually she called a supervisor over and he waved me through.