It could be an “empowerment” issue.

Dresses and fancy preparation are empowering. They show that this person manages their life well and is successful. That of course all sounds positive. Only problem is, to someone struggling with that issue, it can be intimidating.

I struggle to find a good way to express this, but guys like myself since school have grappled with a perception that women “have more social power than them”. Even if the guy isn’t a total loser with a rented home that consists of a TV and a pillow, girls are viewed as a pedestal-standing respected social icon by comparison. That’s definitely not universally actually true, but under young hormones it seems that way.

Hence why pajamas, glasses, or to extend further: VTuber streamers that joke about failing basic life skills, or not showering that week, are often a successful endeavor. They show someone more humanized, disempowered and flawed. Question is whether a woman is okay with accepting a bit of that debasement to put someone at ease.