"Not Even" by Kenneth Cole Reaction ($72.95 at zappos.com)
Jeans or slacks (just make sure they're long enough).
"R7859" by Lumiani ($29.95 at zappos.com)
This shoe would work well under jeans or slacks, and maybe with a flirty (but not poufy) knee-length skirt.
"Cos I'm Hot" by Kenneth Cole Reaction ($201.95 on zappos.com)
Yes, I actually think this is attractive. Do not wear it with a skirt, capri pants, a dress or any item of clothing other than jeans or dark colored slacks. The pointed toe and thin heel make this boot more attractive than your "run of the mill" honkey-tonk clunkers (which many sorority and wannabe-sorority girls seem to love wearing with mini skirts. Gag.).
"Flo" by Anne Klein New York ($403.95 on zappos.com)
This is an incredibly attractive (and expensive) shoe for going out. It's a classic color (that can go with just about anything, just so long as you're not wearing metallic colors anywear other than your handbag or jewelry) and style, and doesn't look like it would be terribly uncomfortable.
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