Oh for sure. Angelica would love to see him all done up in that for her. (Playing with her food)
Ironically I think Roland's normal outfit but disheveled is what does it for her most. (That or anything to do with furry stuff).
It's a small headcanon of mine that Angela's robot body in LobCorp was absent of any sexual components besides her general shapely figure (no nipples or genitalia, basically a Barbie doll anatomy situation). So I personally think that she doesn't have much of a sense of modesty. Angela never really needed one since she was always fully clothed and never really had a 'need' to get naked anyway. She'd know on a logical level that she was made to be visually appealing, including sexual appeal with her figure, but Angela herself doesn't strictly view her own body in a sexual sense besides being aware of how others might perceive her physical appearance. (Very specific kind of ace mood.) Whether she retains that kind of blank body or if she gains those features like on a human body.
What I'm saying is that, for Angela, she may have the view of clothing being more akin to different types of accessories than anything else. So she'd probably be interested in trying out a lot of different things. Including more racy ones like lingerie or costumes which she'd want to show to Roland.
I enjoy the idea that she walks up to Roland and just yanks open her shirt to show him a new bra, and he jumps half a foot in the air. Or she tells him she wants to show him something new and she's standing there in a bunny suit or something. She'd enjoy seeing his reactions but at least until she figures out what she likes it'd be for her like she's trying on different earrings to show off to him. Except those earrings also happen to give him boners.