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Before taking the rabbit down the boot lacing rabbit hole, so to say, Id recommend considering what purpose the boots will serve and deciding on the proper boots for the task
The Metropolitan Museum of Art describes the Zig Zag collection as: a series of gowns that advanced the exquisite opulence of this prophetic New Look Each [dress] exploited the lavish drapery and controlled tailoring of Diors New Look, but with novel emphasis on asymmetry that was to become a Dior leitmotif. (Met) Daniel James Cole and Nancy Deihl note in The History of Modern Fashion (2015) that Harpers Bazaar declared him agent provocateur and hero of the day' (209)
Dresses with a belt or a fitted top and flowing skirt are perfect for this body type
4) Can I wear this more than one way? : If I can dress it up with heels or down with sandals, its a yes