Outfits for First Dates

[PartlyDress]

help me with some style ideas for two first dates I have lined up. One is Friday night cocktails, the other is “Straight from Work” where work for both of us would be Chinos plus Polo or casual shirt.

I live in an unglamorous/very understated place so nothing extreme.
50, 5’ 8”, size 10 in M+S

Do you have any preferences? E.g

Dresses or trousers or jumpsuits?
Heel height?
Fabric preferences or hates?
Are you a "I want to show off my assets" type or a "I want to show off my one of a kind dress" type ?

And last but not least- budget if you're thinking of buying new. If you're not thinking of buying new what do you already have?