QUESTION: Allison from South Bend, IN asked, “Can you wear heels with rolled up jeans....I have a hard time doing that one...guidelines???
ANSWER: This it is a very trendy youthful look, and is one that can also take a "mom's errand" day to something more fashionable
On the shoe - try a heeled oxford style shoe (like the one pictured here from Verandah, A Shoe Shop in Granger, IN). This is my favorite oxford this season - perfect heel height, and with the pretty bow (rather than laces) it makes this masculine trend a little more feminine.
Next, on the jean. 
Be sure that the roll of the jean isn’t a perfect cuff….the look you are going for is intentionally unintentional. …and again, if you try this look and are unsure, then the answer for you and your style is no!
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