Brad Bennett, Style Blogger

Do: Menswear. Boyfriend jeans, worn-in button-down shirts, beat-up coats. Girls in Barbour jackets, forget about it.

Faith Connexion Cropped boyfriend-fit straight-leg jeans, $300, available at Net-A-Porter.

Don't: Silly hats. Not a day goes by that I don't see an otherwise great-looking girl ruin her whole outfit with some silly little fedora, "military" hat, newsboy cap, or some awful crocheted mess.

Halogen Leather Belt Fedora, $38, available at Nordstrom.

What should Chicago girls try more often?
I'd love to see more natural. Natural skin color, no bottle tans. Natural hair color, no highlights. Less makeup. It's refreshing to see girls embrace what they have, as opposed to trying to cover it up.


Photo: Courtesy of Brad Bennett