These oxford booties can be tricky, and I'll admit to having a difficult time styling them without an actual model. But here goes: Flat oxfords look dowdy with a dress or skirt that doesn't fall above the knee or mid-thigh, but you'll look like a school girl if the dress or skirt is pleated. Here, the dress transforms into a skirt by adding the chunky sweater. Only let a bit of the dress peak out at the bottom, and create a continuous line from leg to shoe so you don't appear to have flat duck feet.
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