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Tory Burch Georgia Ballet Flat Website / Nordstrom / Amazon / Zappos Tory Burch shops: website, Nordstrom, Amazon and Zappos Franco Sarto You could try a pair of tasseled loafers for a hip, preppy look

I would be careful about aiming for rumpling from a fit that isnt right, but at the margins it can be nice, for example a shirt that is a little more blousy in the waist, tucked into a neat waistband

For a seasonal twist, consider corduroy pants in the fall for a warmer, textured look

The flattering corset construction enhances your waist while the adjustable lace-up back creates a customized fit that feels secure and comfortable