I like to wear Western (cowboy) boots, but I have had heels put on them.
The first pair, Dan Post's grey with silver trim I had 4 inch heels put on, and the next pair of black Tony Lama's got 5 inchers.
I just got a pair of beige ostrich Noconas and had another set of 4 inch heels put on. They are all medium-wide tread heels except for the Dan Post ones, and they are spikey...a little TOO spiky for me, but fun to wear anyway.
Each time I had them done, they only cost me about $30.00 each..pretty fair I think. That's over the original cost of the boots, which range from $400.00 to $700.00.
With my Gloria Vanderbilt size 10 Petite, boot-cuts, mid-risers, woman's jeans in classic blue color, I also wear a western blouse (yes, with the buttons on backwards) and my "Little Joe" hat and the peacock feather, I present as a mixed bag of gender. If the colors are mixed well on the blouse, I can wear a nice wired bra and it isn't too obvious...at least not anyone has said anything yet.
I like Vasserettes with a wire and they are the most comfortable I can find for me. I wear a 38B or a 36C interchangeably. I try to get bras with all the hardware and adjusters in the front if I can..but not the Vasserettes..they have the adjuster right behind the top of my shoulders and they will show in solid colors and under a tee shirt, so I like to wear the extra splashy colors anyway.
Back to the shoes thing, I also have some woman's joggers shoes too...and I look for ones with a decent higher heel. They come with about a 2 inch heel and I add a pair of Dr. Scholl's jell inserts for the extra height. I just stay away from pink, but I like baby blue and turquoise with white trim and some rather female designs on them. The andro look works with them.
If I tuck the jeans into the boots, it gets very obvious...but outside they send the male signal. I like to wear trouser socks with them, they are like nylons, only shorter...not short like Peds, but at least knee-high.
Around home, I wear some strappy heels..all over 4 inches, open toed and box-toed too, but I like to wear the black trouser socks to keep the contrast down...as I live in a mobile home park and I have neighbors near to me.
When I have to go male, I wear Florsheims in brown or black or grey...but I still wear the women's trouser socks at least. I just get them in the colors that match closest to the shirt or tie I am wearing.