Picking a new pair of boots is hard, mostly because buying them is a serious commitment — boots are typically pricey, they have to be comfortable enough to wear pretty much every day, and truthfully, they need to be durable enough to (ideally) last more than one season. But with all the different shapes and sizes (tall, short, pointed-toe, square-toe), colors (black, brown, white), and fabrics (leather, pony hair, velvet), finding The One gets even harder.

To jumpstart your seasonal shopping, we're laying the footwear groundwork: The perfect leather boot. While color and silhouette are up to your personal preference, if you're looking to upgrade your solid, wear anywhere, anytime shoe, this is where you'll want to begin. Leather boots are sturdy enough to take on those morning commutes and errand running, but still manage look pretty damn good. And if you're not sure where to start when it comes to fall boots, look to the 30 options ahead. They're worth it.