That is totally up to you, my friend! My sizing chart is based on the diameter of the pasties. Many people feel most comfortable with a pair of pasties whose diameter matches up the diameter of their areolas, or a little larger. Some find they like to go a little (or a lot!) smaller or larger than their areola. If you’re not sure, for your first pair, I recommend going with a size close to your areola measurement. You can always extend your collection later to include multiple sizes and styles. Additionally, I offer custom sizing in any size you can imagine. There is no “too big” or “too small”. You are perfect exactly as you are. Just send me the diameter of your areola, and I’ll be happy to tailor a gorgeous pair of pasties to your specifications.