How to Choose Hiking Boots That Won't Hurt Your Feet.Make sure your hiking boots fit perfectly with these tips, so that you've got some spring in every step:.When you're trying out hiking boots, make sure that you're wearing the type of socks you'll wear when you're on the trail.If your toes seem like they're up against the edge of the boot, that rubbing could become a literal pain during a long hike. .Take the shoes for a stroll around the store, so you can really get a sense of how they feel on your feet. .To get the perfect fit, you might need to add insoles to increase the support and comfort for your feet.