A flat shoe that hits right above your ankle still shows off lots of leg without throwing your proportions off. We love Chelsea boots or Dr. Martens.
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Pair this preppy shoe with a contrasting style, such as a '60s shift or sweater dress. Stay away from pleated or plaid, which could look like a school uniform.
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Sleek pointed toe works to elongate your legs and lend a professional, grown-up vibe to your ensemble.
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The key is to choose a boot with a flat sole or heel & enough structure so that it neither slouches down nor clings to your calves.
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