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Every time I watch the 2nd family Guy Star Wars parody I keep forgetting to ask this but recently I saw it again.

Near the end at the point where Lando and Chewie break off from the Rebel Fleet Chewie (portrayed by Brian) breaks the Fourth Wall and points out in that scene Lando is wearing Han's clothing

and this is roughly the same scene in the actual movie showing that Seth MacFarlane was not just screwing with us

now here's a comparison between what Han normally wears and what Lando wore when he was on Cloud City

I am wondering, why did Lando dress up in Han's clothes? It's an awful coincidence that he decided to have a change of clothes and happens to look like Han's. Has it got something to do with how he was piloting the Falcon or is there a production reason for this? Does the novel state than Lando was wearing Han's clothes (or acknowledge that he dressed in clothes similar to Han's)?

From the New Orlean Comic Con in January 2011 (see below video)

Host: The real answer is that costume designer John Mollo decided to put him in the same clothes didn't mean anything as they [Harrison Ford and Billy Dee Williams] were actually sized differently.

The fan answer or the universe answer is it's actually part of the Corellien Core[/Corps?] group. If you look at Han Solo's pants he's got those red marks on them and stuff it's from the old army basically, so it's the same uniforms.

Billy Dee Williams: Yeah we're all in the army. I started as a Steve Wynn, owning Las Vegas, only to join the army to become a, I guess I was a General or something.

Host: I think we should start a new rumour that you left all your clothes on Cloud City because you had to get out of there so fast and Han had plenty of clothes on the Falcon. How's that work for everybody? That's my new answer.

Basically it's an old army uniform. It was never meant to mean anything significant.

Youtube video

Lando left Cloud City with nothing but the clothes on his back. He was on the Falcon where Han presumably kept all his clothes. He borrowed Han's clothes since carbonite Han doesn't need them.

Hard to say in the storyline. From the filmmaker's perspective though... the change of clothing is another visual cue that Lando has abandoned his commercial interests and is now one of the rebels.

Plus, Han's outfits just look cool. Lando's first outfit would look a bit fruity on the Millennium Falcon... I mean, this is Star Wars, there's no place for a caped crusader.

The reality is this is yet another example of George Lucas trying to cram tie-ins and connections down our throats even if it doesn’t make sense. He’s clearly trying to show that Lando is taking over Hans role for a while. We get that when Lando is piloting the Millenium Falcon. Do we need to have it underlined and bolded for us by putting him in Hans clothes too???

It’s similar to how he insisted on putting C3P0 and R2D2 in Episodes 1-3. Why the hell would he make it so Anakin built C3P0 and also had R2D2 as his primary droid other than to create bull crap connections for no reason at all.