Shop your Hourglass Shape. Women's choices for Plus and Missy hourglass clothing. The best way to tell if your shape is an hourglass is to take your measurements. If your bust and hip measurement are the same or close to the same, and your waist is smaller, these tips will work for you. First, anything that wraps or ties around your waist is a must. When you wear something more fitted at the waist, we get to see a silhouette. Shape is good. If you prefer something on the flowy side, make sure that it tapers in at the waist so that we can still see shape. Another rule about wearing something flowy, not just for hourglass, but, for every shape is: if it's flowy on the top, then it needs to be fitted on the bottom and vice versa. Flowy + flowy = tent. Don't do that to yourself, let us see you!