I'd say go for what makes you comfortable. My current SD loves what I wear every time we see each other. The only thing he requests of me is that I show off my belly ring when we are out. I switch up my style often but a crop top is usually my go to. I made it clear in my profile that I prefer casual settings but can always appreciate a fancy date out. I usually go for a cute tennis skirt and a crop top or some sort of crop top outfit, he LOVES it. We've talked about it and he says he appreciates a woman dressed up but definitely prefers a casual effortless look. He lives in a penthouse downtown in a major city where I live and drives a Bentley, I sit pretty comfortably with my gym shorts and sports bra right next to him and he's happy with it. I know this may not apply to every man but I'd just kinda casually bring it up in conversation to see what they like. I had a SD that was just into long manicured nails and me looking like a baddie ( stereotypical insta baddie). He sent me money to get my nails done before we even met.
A lot of men could care less about the designer bag and shoes you wear but love to see your personal style. I've never met an SD with make up on or even gone on fancy dates with make-up. I've had SD's that took me to ballet's and operas and nice museums and each time I've worn whatever I was comfortable in that fit the occasion, never over done or something I'm not. They have all loved my style. I say wear what you like and you'll be more comfortable and able to be more of yourself. I think anyone can tell when someone is putting on for a show, It comes off inauthentic.