Ankle Boots w/ shorts. For denim shorts, pair them with black ankle boots while khaki shorts will look great with brown ankle boots. Neutral color tops in white, black, grey or cream will definitely be the perfect match with denim short. Tuck in the top to make it more appealing and belt the shorts with a thin leather belt that matches your boots. Accessorize with a medium size handbag that will complement the top or the boots, necklace, and earrings. Finish off with dark sunglasses and.