Hi, Kimberly!
I'm surprised you didn't compare the size of the flowers to drill bits, hole saws, or socket wrenches - and I would have understood those comparisons as I know my way around 'the tools' too!!
The color of the blouse being a white/cream color, even if it's mostly covered with those flowers, tend to make it more a summery outfit. A darker color, in general, is more for fall/winter wear. The hose color would affect how the outfit looks overall given the time of year it's being worn.
Calf-length denim skirt with a button front? Hmmm, it still might have a tendency to gap open at the very bottom (between the last button and the hem) and see those hairy Sasquatch legs of yours.

It's too bad Kaye(SO) won't let you shave the legs, she's missing out on a very sensuous and sexy feeling, IMHO!
Okay, the Sasquatch legs are reason enough to wear the trouser socks as opposed to thigh highs or pantyhose. The suntan color would be more 'summery', or even a taupe or coffee color, instead of black. Nude or pink trouser socks as Donna suggests? Hmmm, might work if it covers up the hair!
"Fashion sense of a guy" -
Hmph!! I know some hetero non-CD's who have wonderful fashion sense, and they're not models, either!
Life in general is so much better if you can learn to laugh at yourself!!
I know that Kaye(SO) and yourself have been working through things and doing quite well, and that says quite a lot about both of you - the art of communication and compromise, seasoned heavily with love and understanding.
I'd love to see a pic of you in this outfit - provided you can get the camera back from your son!!
- SL