The key to buying a great investment piece is to make sure it functions for more than one season. You can wear it now and later? Totally worth it. Here, we’ve chosen a few statement-making hero pieces—a fringe jacket, denim dress and printed pant—that not only make an outfit, they transition beautifully from chilly to hot temps. Basically, once you’ve calculated the cost per wear, they’re almost free. Almost. Watch and learn.