or multi-hour dates with Ladies who truly are "one gentlemen a day" types, is that I get to see them both dressed up, and casual.
I like "ebb & flow", and when she can feel comfortable 'letting her hair down', I always take it as a compliment.
Recently I had two extended evening dates in a row with a Lady. At the end of the first evening's date, around 11pm, before she left, she pulled out a pair of yoga pants, a sports bra/top, and socks/sneakers, and proceeded to get dressed, pulling her hair back in a bun. "Casual Hot" I'd term it. She was going off to the gym (she is a bit of a night owl). Seeing her get dressed was a turn-on especially when I saw she was going 'commando'. Made me want to get a guest pass for a day and go with her, lol.
I do appreciate when a Lady takes the time and effort to 'doll up' to her standards. I'll appreciate her beauty in whatever form she decides to share it with me in. But as long as she is clean, and wearing a smile, the clothing is secondary.
Now, if I had been in your gentleman's shoes, knowing it was going to be an extended date, I probably would have offered to give you a nice hair shampoo and scalp/face massage to help you move past embarrassment and have some giggling shower time.
I find this realm often brings us serendipitous moments that can really give us lasting memories.