Buying your first pair of cowboy boots can seem intimidating, particularly if you’ve never received cowboy boots as a gift or hand-me-down in the past. But there’s no reason to feel nervous. With a little planning and research, your cowboy boots can quickly become your new favorite wardrobe staple – one that will last for seasons and years to come.

Are these boots made for walking?

The first thing to consider is whether your primary reason for buying cowboy boots is for function or fashion. There’s no shame in wanting to make a fashion statement. If you’re planning to use your cowboy boots as work boots or riding boots, your requirements will be a little different than if you mainly want them for everyday wear or an evening out.

If you’re looking for cowboy boots for working or riding, the first aspect to consider is the heel of the boot. You might think a nearly flat or flat sole would be best, but you’ll want at least a slight heel – something in the range of 1.5 inches or a little higher is perfect for keeping your boot from sliding around too much in a stirrup. You don’t want anything with too tall a heel for riding, though, or it could leave your foot stuck in an awkward position.

You’ll also want to consider the shape of the toe. A pointed toe is what most people envision when they think of the classic cowboy boot, but if you’re going to be wearing these boots all day and working hard in them, you should try out boots with different toe styles. You might find that a rounded or square toe fits your foot better, and that will go a long way to leaving you feeling more comfortable in your boots.

Are you ready for your close-up?

If you don’t plan to wear your boots to work all day, you should give some thought to what kind of wardrobe statement you want to make. Do you want these boots to help you blend in or stand out? If you don’t want your new cowboy boots to be the central focal point of your outfit whenever you wear them, consider a more traditional or neutral leather color like black, tan, or dark brown. Then again, maybe getting attention is your whole goal! If you want to make a statement, consider a more exotic leather like snakeskin or lizard, splurge on a pair of alligator boots, or look for trim and other details in eye-catching hues like bright red and turquoise blue.

Take your time!

Regardless of whether your boots will be fashion-first or purely functional, getting them fitted correctly is the key. Take your time when you’re trying them on. Make sure you’re wearing socks, and try to use socks that are similar to the ones you plan to wear with your boots every day, rather than something too thick or too thin.

When you’re trying on cowboy boots, you want them to be snug, particularly around the calf, but never painfully tight. If you’re buying real leather, you should prepare for a breaking-in period that could last a few days or a couple of weeks, depending on how often you wear the boots. During this time, the leather will soften and start to fit itself to the shape of your foot and calf, and pretty soon you may discover that your cowboy boots are the most comfortable footwear you own.