haven't worn in years but feel that they might be the thing that elevates from day wear to sexy?
I hope you find something that is comfortable and makes you feel good and sexy, so that you can forget what you are wearing, relax and enjoy the date.
Is sexy for you that you look attractive to the male gaze or that you feel comfortable and confident in your own skin?
High heels that you haven't worn in years might not be that comfortable. Discomfort would show on your face. It doesn't sound to me as if uncomfortable shoes would be idea for a first date.
This is uncomfortable close to some of the issues raised in the Olympics for men v women's uniforms. Women being expected to wear skimpy clothes for the male gaze, so they can't be comfortable when in public.
No one wants to feel a frump but putting your feet in high heels doesn't seem the right way forward for me.
I think it is the nature and quality of the fabric that elevates from day wear to evening. Hope you find something that makes you feel great.