Hello. What do you think Aizen's fashion choices would be? To go to work, in casual clothes, at home, etc. I saw someone's headcanon about him wearing dresses. What are your thoughts in the matter?
Sorry for the delay - I haven't been in a headspace to answer asks for the past couple of months.
I sort of talked about my hc's on his fashion here. I think Aizen is someone who tries to blend in to the crowd, but the clothing items he wears are of great quality (I can easily see him agreeing to dieworkwear/Derek Guy's comments!). We can already see from how he dressed his own army and Orihime that he has particular styles and design choices he prefers.
In official art of him not wearing his Lieutenant/Captain/Hueco Mundo/Muken uniforms, he is dressed in "classic" menswear styles. (I haphazardly put this collage together on photoshop lol.)
Kubo had a convention in Italy back in 2017 where he sketched portraits of different characters in modern clothing, and this was his sketch for Aizen:
As for him wearing dresses, I don't see why not. I'm not interested in making commentary on other people's headcanons. That's the fun in it - anyone can imagine anything to their hearts content.
Thanks for the ask!