It's such a stereotype flirty move. I've done this to a couple guys I've liked on the street or the public transport but 99% of the time I chicken out and can't get to do it even though I want to.
In my case most guys don't react, probably stunned by my courage or questioning if they really saw me wink. The few times that they reacted has been a shy smile and continue walking.
One time it actually led to sex with the guy I winked to. We were on holiday. He was sitting at a bar with his boyfriend. I walked passed, winked at the one I liked, 10 min later went back to sit down with them. Exchanged numbers. Next day he was fucking me

That's my hottest story and outcome with this and frankly I love bragging about it because I'm not that type of person and this was really out of character for me.
Locking eyes and winking sounds so cinematic and subtle and that's probably what excites me about it. No apps or modern ways. Such a vanilla move, but takes balls.
What's your experience, has anyone done it to you, have you done it, how did/would it make you feel?