Erin on www.dressaday.com did an entry today about her many pairs of penny loafers. I think I have owned two pairs of penny loafers in my lifetime. What I do wear on my feet is cowboy boots. This is my collection of cowboy boots. This is actually the bulk of my shoe collection.
You may wonder why this Boston-bred New Yorker wears cowboy boots. The simple answer is comfort. I have wide feet. Finding women's shoes that fit my feet and don't depress me isn't an easy task.
While the default width for women's shoes is a B, the default width for men's shoes is a D. I wear a D. I suppose I could wear lace up oxfords, but that would be simply depressing. These boots are all men's boots. The cowboy boots look fun , work well with skirts and feel good on my feet.
Because my foot is a relatively small one for a man, I can usually find boots on sale. because men tend not to go for flash, I can usually get a funky pair. Life in cold weather is good. I'm now transitioning out of boots now that the weather is warmer and am moving into clogs and sandals. The boots are actually more comfortble.
This single pair of short motorcycle boots was purchase in the "western footwear" section of the Sierra trading post catalog. I don't know if you would classify them as Western wear, but they are super comfortable. I love their tough girl look.