A classic suit is the gift that keeps on giving. Not only is it chic, but it's timeless and appropriate for tons of different occasions. You could feasibly own the same blazer-and-pant combo for several decades (talk about optimizing the cost per wear). But the challenge there is coming up with fun styling ideas so it doesn't feel like something you've owned for a lifetime.
Leave it to Rosie Huntington-Whiteley to demonstrate one way to keep things fresh: cinching a jacket at the waist with a belt bag. The retro accessory is coming back with a vengeance, and whether you're sold on it or not, you have to admit—it's pretty functional. Also, in Rosie's case, it looks effortlessly cool. (It doesn't hurt that the belt bag is part of Gucci's ever-covetable Marmont collection.)