Amazon April showers may be necessary for May flowers but there's nothing worse than getting caught in a rainstorm unprepared-i.e. while sporting your fave leather flats that are definitely not waterproof. The good news? There are tons of totally chic rain boots that look chic and will still keep you dry this spring. There's the classic tall silhouette, chunky lugsole styles, Chelsea-inspired designs, and so much more. Best Affordable Rain Boot Style: Fubotao Mid Calf Rain Boots, $25.99Best On-Sale Rain Boot: Hunter Original Tall Rain Boot, $152.