Never had sufficient courage to try it before.
I rode a BMX-style bike with smaller than full-size wheels. Nominally 20" (406). A folding bike with handlebars and saddle at adult height.
The top of the frame is 25" high so I had to lean the bike away from myself to lift my leg over with some level of modesty.

I was enjoying myself so much that I rode around the block several times.

No problems with the skirt flipping back.
My outfit was:-
A-line skirt (my usual length of 18") - above knee
Black medium support tights (around 20 denier - pantyhose)
Black patent, 3 1/2" high, block heels with a strap (Mary Janes)
Yellow, hi-vis, cycling jacket
White crash helmet
Black cycling gloves