Ask yourself five key questions before buying new boots.
1. Where are you going? As a general rule, you’ll be more comfortable with the lightest boots appropriate for your planned terrain. Dayhiking on trails? A well-cushioned, flexible low-cut should do. Carrying 50 pounds off-trail in Alaska? You’ll want a high-cut, heavy-duty boot. Once you’ve picked a category, don’t fixate on weight: With footwear, fit trumps a few ounces.
2. Do you need more (or less) support? If you have weak ankles, choose higher-cut boots with maximum stability. The extra weight is well worth the joint protection. Likewise, if you’re prone to sore feet, opt for stiffer soles made for heavier loads than you typically carry. Conversely, some trekkers need less structure and can wear trail runners for ultralight trips or 2,000-mile thru-hikes.
3. Waterproof? You need weather protection for soggy trails, certainly, but don’t always pick a waterproof shoe for just-in-case scenarios. If you rarely hike in cold, wet conditions, you might be better off with footwear that’s more breathable and fast-drying. If you’re getting a low-cut boot primarily for summer use, an airy upper can prevent sweaty feet—and blisters.
4. What size? Feet grow and change shape with age and mileage. Get yours measured on a Brannock device (gauges length, width, and arch length) by an expert salesperson who should be able to recommend specific brands and models well suited for your foot’s shape. To best simulate your on-trail shoe size, shop in the evening, when your feet will be slightly swollen.
5. Do they fit? Try on boots with the hiking socks and insoles you intend to use. If you can’t slip your index finger between your heel and the back of the boot, try a bigger size. Wear your top-pick boots for at least 20 minutes in the store, then answer these focused fit questions: Do your heels slip? Test movement on an incline board so you can check fit on ups and downs. Feel any pressure points? Do your toes feel pinched or bang the boot front? Remember: A boot may stretch in width, but it can never get longer.
Pressure points may not be readily apparent in the store. For a good visual, remove both insoles and stand on them. The more similar the shapes of your feet and the insoles, the better chance of a good fit. Red flags: Places where your feet overhang indicate likely snug spots. A boot may be too loose (a recipe for blisters) if its insole is wider than your foot.
Because manufacturers use differently proportioned lasts, stick with brands that you know fit well. If you’re unsure about sizing, order three pairs at once (your best sizing guess, plus a half size bigger and smaller) to compare. Zappos.com offers free shipping (on returns, too!), and backcountry.com and rei.com have no-questions-asked return policies. Be respectful: Restrict test-wearing to clean, indoor surfaces.