If you’re opting for a shorter pant or skirt, make sure to wear the right shoe. “Update your shoes by choosing a pair of heels, boots or flats with a slightly pointier or almond-shaped toe,” says Stoll. “This will help elongate your leg line and helps you look more polished. Avoid short, rounded toes, since these can make you look shorter and frumpier.”
If you want to wear heels, more power to you, but don’t feel like you have to. “The perfect level of style is when there’s some comfort in there,” says Rothman. So swap out your five-inch pumps for kitten heels, platform shoes or wedges so you can wear heels without the pain. Try these extra-cushioned, low-heeled ankle boots from Hush Puppies. They’re comfortable, stylish and even sensibly water-resistant.