I’ve read a lot of posts about Lilo and Stitch 2025 and I see the topic of Pleakley’s cross-dressing being brought up quite often.
I haven’t watched the remake and I doubt I will so my goal is not to compare Pleakley from the animated movie(s) with Pleakley from the live action. I just want to share some of my thoughts on this topic too because Lilo and Stitch has always been one of my most favourite Disney franchises with Pleakley being one of my most favourite characters of all time, not to mention I’m getting into this franchise again so I’m starting to have more to say about it.
Just note that those are only my thoughts that I decided to share so I’m not claiming to be a Pleakley expert or anything and I’m sorry if I’ve worded anything wrong.
One of the takes made in favour of Pleakley NOT cross-dressing in the live action is that him disguising as a woman is taken more as a joke and hence seems offensive to trans people. I’m not going to deny that it was definitely used for a comic effect in some scenes but I think it’s also fair to point out that Pleakley seems to be genuinely interested in feminine clothes and feminine looks in general. Otherwise he wouldn’t put on a wig and admire himself in the mirror (or even keep the wig after he didn’t need his disguise anymore) in the campsite scene.
Is it a minor detail? I’d say yes. But it does imply that Pleakley is interested in feminine clothes and this is why it’s grown into such a significant part of his character in the next movies and in the series.
Pleakley is an Earth expert, and he’s spent many years of his life studying this planet and familiarizing himself with its customs and traditions (which we see A LOT in the series, from Pleakley doing yoga to singing Christmas carols), and there’s no wonder Pleakley would get interested in the Earth attire as well. I don’t remember where I read it but I’m pretty sure Pleakley didn’t even know that clothes he took in the og movie were feminine* so it only kindled his interest. It’s unknown, and it makes it exciting.
An interesting thing I find about Pleakley’s character is that despite leaning towards feminine clothes and clearly favouring them (and even disguising as Lilo’s aunt on Earth) he doesn’t stop wearing masculine clothes. He wears them both depending on his mood, and nobody comments on his preferences.
One of the episodes from Lilo and Stitch: the Series that really stood out for me in regards of Pleakley’s identity and the way other people/aliens treat it is the episode Nosy, the one about an experiment that reveals secrets and loves gossiping.
We learn that Keoni, Lilo’s crush, has a crush on Pleakley, and when Nosy reveals that Pleakley is not a woman, the first thing Keoni does is asking Lilo about Pleakley to make sure he’s indeed not a woman. What is his reaction after this confirmation? He’s just glad that it was revealed because yeah, he’s a simple straight guy (who’s also much younger than Pleakley but this is not what we’re talking about now).
Keoni never asks why Pleakley, a male, would even wear dresses, have long hair, and call himself an aunt. As I mentioned above, literally nobody in the series (and also in movies) cares about the way Pleakley dresses. They never asked him to explain or God forbid justify his preferences.
They’re cool with it, and it makes Pleakley’s presence in the franchise as natural and genuine as possible because the way he dresses is not his whole character, this is something that blends neatly with his other traits to make him a memorable and compelling character.
As I said in the beginning, I haven’t watched the remake so I have no idea how they pulled off the rest of Pleakley’s character but I’m one of those people who’s convinced that Pleakley (read: an Earth expert who was sent to that very planet, getting a chance to learn more about its customs and traditions and accidentally stumbling across Earth feminine clothes just to embrace it as a way of self-expression and find comfort in it) is not Pleakley without cross-dressing.
*Added some more thoughts on it in the tags because those are mostly me thinking out loud and I wouldn’t want to ruin the structure of my “essay” with random babbles.






