I think I do. I don't go out and buy something new, but I choose an outfit from my wardrobe that I think would go with what he is likely to wear. Like right now, I am dating a 42 year old professor type. So I go with elegant dresses, more mature, not too revealing.
Being petite, I tend to look very young (often get mistaken for a 16 yr old,) so I dress in something that makes me closer to my age when I date an older man. I also wear heels on most dates when with someone much taller.
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In my opinion you dress for your comfort and mood on that day. Once I had a date with a pretty girl, she was wearing a beautiful dress and heels. I had a feeling that the dress doesn't fit her well.. I didn't mention anything, but i complemented her... But still she was not very comfortable, all the time she was trying to check whether the dress is alright.
We didn't feel a romantic connection; but we continued as friends, once i asked her why she was nervous on our first date. Her answer was closer to what you mentioned. Since I'm taller, she wanted to wear heels on that day. And her favorite dress for heels was a little tight (later she told thanks to her fast food addiction). So she he wore her favorite dress and later started feeling uncomfortable.
It's just an experience. what i meant to say that - go for the dress suiting your mood...