AAOx4: @joycon: It is complicated. He doesn't 'like it' per se, but does it habitually as a way quelling or appeasing others. He sees himself as not human, an object or possession, so he sometimes regressed into a state where he wants to make himself 'pretty' like an intricate ornament you'd put on a shelf, so he's less likely to be broken / damaged.
AAOx4: @joycon: Wearing dress --> you seem harmless and inoffensive. A 'wallflower' in the literal sense so others (mostly the entities that harm him) don't see him as a threat. Also brings him closer to the dolls he identifies with: Pretty and human seeming by appearance, but inside they are just artificial creations, objects built to amuse humans.
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He looks so happy being a 50's diner server