The invitation to last Friday night's Reader party celebrating the Best of Chicago asked attendees to "dress up a little"—and they did. Above, a pair of shoes with pockets on the toes—for change?

A study in the effective use of contrast: ladylike lace with striped menswear-inspired shorts.

You can imagine one of the bad girls from Mad Men in this vintage dress with hoop earrings (and cocktail).

Kudos to guys who take chances—here, by mixing patterns.