All of my little black booties! Is it ridiculous to have so many? Yes. Do they all serve different purposes? Also yes. I think you should have a stiletto and potentially also a block heel. One is casual and edgy and one if very classic and elegant. I also wear my waterproof lug boots ALLLLL winter. Quite literally. End of fall into early spring tbh. Perfect for the snow and slush and are anti slip. Look adorable with a wide leg ankle jean. The Madewell in the top left are all business. They have a squared off toe and low thicker kitten heel. They’re perfect for jeans or trousers but are definitely not super dressy but also not casual. Lastly; the suede. I just love the option to have another texture. It’s so soft and feminine! I got my true size in all! Hope this helped! LTKShoeCrush LTKSeasonal LTKStyleTip