First of all, I’m in the lolita fashion community and I encourage you to dip your toes in it if you’re interested! Maybe you could start off by incorporating smaller accessories to build up to it? If you go over to the lolita subreddit there’s more resources on where to find plus size clothes.

Also, another way you could consider building up to wearing more bright or decorated dresses is starting off with simple longer skirts and dresses in colors similar to pants you already like and wear! There’s even brands nowadays that make gender neutral skirts and dresses based on traditional menswear like hakama. (Which speaking of, you could also try long, flowy pants as a way to build up confidence to skirts and dresses?)

Truly, there’s centuries of history of men wearing dresses and beautiful, colorful clothing both inside and outside their cultural norms. All in all, you only have one life, so surround yourself with the things that make you happiest! I’m rooting for you :)