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You wouldn't buy a dress without trying it on; follow that rule with a prospective pocketbook. Medina's three approved positions for a short-handled bag: over your shoulder and tucked under your arm; over your forearm (or in the crook of your elbow); or held in your hand. When worn over the shoulder, your bag should fall as close to your center of gravity as possible (around the navel or waist, on average; a little higher—at chest level—if you're petite). Very busty women should avoid carrying anything on the shoulder: They're already being pulled forward by the weight of their breasts, and this aggravates the misalignment.