Fall VERY casual dress/skirt looks?

[Jane Bond]

Originally Posted by Dance-with-me

I'm getting so much help in my "what shall I wear to show my appreciation to my date" thread I figured I'd ask for more!

I'm 53, short (5'3"), curvy (183 nekkid in the morning, and a size 16-20 depending on who makes it) femme who is very quickly recovering from over 11 years of progressively frumpy dressing and looking to expand my wardobe with some essentials (and yes, lingerie as defined in my other thread is an essential). My tits are my best feature,so a little cleavage or a bit of an accent there is always good. But being short and round, there are just a lot of looks that I can't carry off well, plus I just have no overall fashion sense or idea of what might look good.

I'm trying to figure out a fall weather CASUAL date dress or skirt outfit, the type of outfit that would not stand out as totally out of place in a group of people who were wearing just jeans and t-shirts, but would still give me that "look, I'm a GIRL!" confidence boost in a group of generic lesbians (and perhaps draw the attention of a butch in the crowd).

To give some perspective, my summer go-to outfit is a casual above-the-knee soft rayon or light knit beachy shift/sundress and some flat sandals, which doesn't look too dressy in a group of folks in shorts, sleeveless t's and sneakers. But for the life of me I can't think of what would work as the fall/cooler weather equivalent to that.

Ideas? Pictures/links?

I think they sell all sorts of pattered leggings now that fit and flatter almost anyone, then on top a nice tunic length that somehow matches the leggings. And maybe a nice scarf.
Shoes? Got me there all I wear is man shoes. Maybe flats? Good luck & have fun.