My main Wing Chun teacher Dr. G.K. Khoe had a background of Judo and also TaeKwonDo before studying Wing Chun under Master Wang Kiu, who was a private student of I Man (Yip Man).
In my day we always wondered how to handle a good kicker. These days Wing Chun people wonder how to handle a good grappler. Eventually the non-pig headed Wing Chun people eventually conclude that they better learn a bot about the other art that they are worried about as well.
In every Wing Chun class of every Wing Chun club the students practice against pretend kickers, pretend grapplers, pretend knife experts, pretend Boxers and pretend multiple opponents who don’ know how to fight as a group (another subject).
For the beginner that is what you must do. However then when faced with someone who really knows how to attack in a Wing Chun way, whatever you learn in class just does not work. The ideas are still god in theory but in practice you need to tweak your timing and distancing to make Wing Chun work.
But in most schools you do not have real fighters to train against. For that, you must venture out to another school or to just enter some tournament to fight another art. For most this is not too practical and may be a hard way to learn.
My teacher was good against TaekeonDo because he trained that a lot. But we never faced TaekwonDo experts so we did not have this same experience. Of the various masters I encountered I know that Emin Botepe and Kenneth Chung were also good in this area. With the others, the topic just didn’t come up, so I don’t know their skills in this area.
So as a starter lesson in all this, it is good to watch one of the best videos about TaeKwonDo kicking that I used to watch in the 1980’s. It’s my favorite TaeKwonDo instructional video. Now it is on YouTube.