What shoe should you buy next? In this video I explain why the answer is often already written on the bottom of your current pair. Hiking footwear is easily the most important piece of gear you’ve got, but the options and buzzwords—heel drop, pronation, rock plates, waterproof membranes—can make it feel way more complicated than it needs to be. I walk through the big boot vs trail runner debate, why I personally switched to trail runners, and why boots still aren’t “wrong” if durability and rugged use are your priorities. I also break down waterproof membranes and why I changed my mind over the years. Waterproof shoes work right up until water comes in over the top—then they trap moisture and fight drying. Trail runners with a solid synthetic or wool sock can blast through water crossings and feel dry fast, without the hassle of swapping into sandals. Finally, I get into the more technical stuff: using your outsole wear pattern (or a wet-foot cardboard test) to learn about pronation and whether you need a supportive or neutral shoe, plus how heel drop can shift stress between knees/hips versus calves/ankles. I’m not a foot doctor, but this should get you a lot closer to buying the right next pair.