Experiment with heel height and structure; you might be more comfortable in a wedge or a platform.
Consider newer names like Sophia Webster and Charlotte Olympia, two talented designers who test out their high heels by wearing them around their neighborhoods.
The White House has new tenants—surely your shoe cubbies would like them, too.
(We've all stood at the gym, frantically searching both bags for a yoga guest pass, and it's neither pleasant nor cute.) If you can afford to get the bigger size, do it.
Every item in your closet has been around since the Bush administration.
Investment pieces are great, but if your entire wardrobe is 10 years old, it's time for a reboot.
(And if you do, have you been to a therapist recently?
) Bottom line: Buying clothes that truly fit will make you feel great and look great—and that's the whole point.