You could be out on beautiful trail on a perfect day – water below, rocks underfoot, blue sky above -but if your feet aren’t enjoying it, chances are you won’t either. Proper footwear isn’t just important to making the most of a walking tour, it’s crucial. That’s why we’ve taken the time to collect some of our best tips for choosing the right hiking footwear – and guaranteeing yourself happy feet the next time you’re out on the trails.

Be Honest About Your Ambitions. A huge part of choosing the right shoes is understanding the terrain. If you’re exclusively interested in leisurely ambles down well-maintained rail trails or paved bike paths, you probably don’t need heavy-duty hiking or mountaineering boots. On the flipside, if you’re interested in a destination full of uneven paths or rocky ascents (like Ontario!), you should probably put those cute low-tops you’ve been eyeing back on the shelf. As a general rule, if you have any concern about rolling ankles in the places you’re planning to walk (due to the terrain or your own tendencies), opt for stiffer shoes with ankle protection.

Shop Near the End of the Day. Most people’s feet tend to swell as they go about their usual daily routine. So if you’d like to imitate the conditions your feet will be in during a long walk, it’s best to go shopping later in the day. That way, the normal swelling of your feet will help you choose a shoe that fits at the end of a long hike, not just the beginning.

Bring Your Insoles, Orthotics, and Socks From Home. A common mistake people make when buying hiking shoes is that they shop in the socks they happen to be wearing (which, if they’re coming from work, may be thin cotton dress socks). As a result, they choose shoes that fit incorrectly when they’re actually wearing their preferred thick hiking socks. Make certain to try on your shoes using exactly what you’ll wear while out in the real world; including any orthotics or insoles. You’ll be amazed by how much they change the fit!

Be Loyal to Your Brand. If you’ve had a pair of hiking boots you’ve loved for years but need to have replaced, consider buying the same brand. Most manufacturers use the same shape of wooden mold (or “last”) for their shoes, so chances are good that if your last pair fit, another from the same company, even purchased years later, will have a similar feel.

Know What a Good Fit Feels Like. It’s easy to over-think things when buying shoes. Don’t convince yourself that a particular pair fits “well enough.” Instead, pay attention to a few specific details to make sure you’ve got a good match. First, make sure your toes don’t feel crowded in the front; a toebox that’s too narrow will lead to blisters or worse. Second, check the length: with the shoe completely unlaced, stand up and slide your foot forward until your toe touches the front of the shoe. There should be just enough space in the back to stick your index finger behind your heel. Finally, lace up the shoes and see how they feel to walk around in. Check to make sure that your heel doesn’t slip at all in the back (a sure cause of blisters) and see if you start to feel extra stress on the balls of your feet or heel. This could be a sign of a mismatched footbed. That doesn’t necessarily mean the shoe won’t work; it’s just a sign you might need a custom insole or extra arch support.

Remember to Break Them In! Finally, don’t forget to take your new hiking shoes out on some walks prior to your next big adventure. By using them for a number of lighter, shorter strolls, you’ll help them mold to your feet. That means they’ll feel perfect by the next time you’re out on a Hiking Holidays tour!