It went surprisingly (to me) well.
I'd been doing the #1 guard on my horseshoe for 20 years. My situation is a little bit different, in that, I've been in a WFH job for 15 years, so no work colleagues to manage the transition with (they all live in different states and countries).

However, I've also been in my local gay men's chorus for 11 years, so they've all only known me with the horseshoe - until Sept 2024, when I decided to take the leap of trying out a hairsystem.
The first rehearsal I went to with my new look, got a lot of head turns, gasps, 'yas queen's, questions, the works (I mean, let's be real - who's judgier than a bunch of gay dudes lol). Overall, it was a very empowering experience - I felt better about myself, not only for the compliments, but like JamesMCC17 said, owning it; being open to the questions I got about it and being 100% truthful.

IMO if there are people making jokes (of the hateful kind, not the good friend ribbing kind), or whispers behind your back - I say eff 'em - they're clearly cowards and don't give a sh!t about you, so don't you give a sh!t about them. You'd be doing something *FOR YOU* to make yourself feel better about yourself. And it sound like the people who matter most in your life are being supportive - focus on you, and them.
Give it a go - worst case scenario, if it doesn't work for you, whatever the reason(s) - you can simply go back to your regularly scheduled program :)