Hiking Footwear Buying Guide
Get yourself a good pair of footwear to protect your feet, and the trails are your oyster. They come in all shapes, sizes, and colors, but ultimately they all do the same thing; provide a platform to keep you hiking along your chosen path. When setting out to capture the best pair of footwear for your feet, make sure you grab the socks you'll be wearing on the trail. Preferably a moisture wicking, cushioned one that gives the necessary warmth for the environment you'll be exploring.

Application
What is your name? What is your quest?
The terrain, weather, season, and how much weight you'll carry are all factors
First, close your eyes and envision what you plan on getting up to in your sweet new kicks. Only you can decide what you're after for any given setting or situation. Zoning in on how you plan to use and what you hope to get out of your hiking footwear is the best start toward maximizing your comfort and performance out there.
ENVIRONMENT: Choosing the appropriate footwear for your adventure can depend on both topography and seasonal factors. Will you mostly encounter well-maintained trails? Rocky ridgelines and scrambles? Long stretches of sandy beach? A lot of in and out of the water? How about the climate where you live or where you're planning on traveling?
On a macro level, maybe you do most of your hiking through mountainous terrain where it's critical to have a rugged tread on your outsole for traction and underfoot protection, and a good amount of support for those frequent uphill climbs. Or maybe your favorite trails are like those of the wet, soggy Pacific Northwest, and keeping your feet dry with waterproof footwear is a high priority. Getting more specific, you may have a plan to hike the Grand Canyon rim-to-rim in mid-August. Chances are you'll want to look at well-ventilated options to adapt to the hot summer climate of the Southwest.
PAYLOAD: Your payload is most often a function of the distance and duration of your hike, so consider how much weight you carry when your pack is fully loaded. This can help determine the amount of cushioning and support you should be looking for in your footwear. If you mostly day hike and only carry a rain shell, water, and some lunch, you can probably get away with minimal cushioning and support. If you do a lot of backpacking and carry a heavy load, you should probably look into a stiffer design with a solid amount of support.

Style
Ain't no mountain high enough, unless your feet get too sore first
Shop a style that fits your planned hike
It can be tough swimming through the sea of product names and buzzwords out there, but we're here to help sort all of that out.
BAREFOOT / MINIMALIST: Exactly what it sounds like. These are basically really highly evolved socks. Well, kind of. They keep trail debris off of your feet and feature a thin sole to help with gripping the trail. Some rave about this style because it affords the greatest amount of trail feel possible without going fully barefoot. With little to no support, these are best when carrying very little extra weight in your pack. And this isn't a style to jump headfirst into; your feet will need time to adjust.
TRAIL RUNNERS: While not built specifically for hiking, this is quickly becoming the go-to option for many hikers, especially those attempting a thru-hike. Ready to hit the trail straight out of the box, plus the shedding of weight (compared to a boot) can be truly glorious to your feet. Not to mention the multi-purpose factor: you can do actual trail running in them too! They will wear out much faster than a good pair of boots, but it may be worth it in the long run.
APPROACH SHOES: Geared toward the climber that's really just looking to get to the crag quickly, approach shoes have a super-sticky rubber outsole, much resembling the rubber you'll find on climbing shoes themselves. They perform incredibly well on rocky routes though, so you don't really have to be a climber to put 'em to good use. The lacing system is incredibly adjustable, typically starting way down at the toe (again, like a climbing shoe). Plus, in my opinion, these kicks tend to have a cool look to them. A little fashion on the trail never hurt anyone.
HIKING SHOES: Often referred to as a hiking shoe, low hiker or lightweight hiker, these resemble the little brother of big old clunkers. Where a running shoe meets a hiking boot, if you will. They offer more flexibility in the ankle, and while they can still include a half shank for stability, they typically don't, becoming more flexible underfoot. Usually chosen for shorter trips, they're great for day hike or weekend backpacking adventure. They're also lightweight, so your feet won't get tired from dragging extra ounces.
HIKING BOOTS: You could really split this category into two: mid-cut hiking boots and high-top hiking boots. Generally speaking, the higher the cut, the greater the protection, stability, and ankle support while carrying heavier loads. It's also true that taller hiking boots tend to be heavier than the ones that reach just over the ankle. Hiking boots are probably the most common style you will see on the feet of backpackers and bushwhackers. Heavier-duty models start transitioning into more technical trekking and mountaineering territory, as well as winter season applications.

Materials
Living in a material world
Weight, durability, and breathability are all heavily influenced by materials
In short, you're either going to go with leather, synthetic, mesh or most likely, some sort of combination.
LEATHER: A pure, all-leather boot is nested deeply in the past of hiking, but that doesn't mean you can't find them being used out there today. They're incredibly durable and over time mold to your foot, getting softer with age. Many hikers find the soles wearing out before the uppers, sending them to a cobbler when they just can't kick their trusty old friend.
SYNTHETIC: Fast forward to the here and now and synthetic materials like nylon, polyester and synthetic leather (PU/TPU) are kind of taking over. Lightweight and quick-drying, synthetics are highly versatile and find their way into the design of most modern offerings. They're also nice and durable so you can still kick rocks aside.
MESH: Breathable mesh is the cream of the crop for warm weather adventures. This material allows air in and out of your shoe constantly, making especially hot days much more bearable. A little on the delicate side, it is often incorporated with other synthetic materials, such as a cage layover, to enhance the durability. The best part about mesh is it dries incredibly fast, so if you land in a puddle or trek through a creek, you'll be dry again in a little while.

Waterproof vs. Breathable
Pick a side, then argue about it with another hiker.
You can have both with the right technology
At one point in history, finding your comfort zone within the hiking community would require you to take a firm stance in the waterproof versus breathable debate. To many, the issue with waterproof footwear is that it doesn't perform as well in warm to hot conditions. With traditional waterproof barriers (think waxed leather), moisture has no easy way to escape from the inside out and can lead to discomfort from sweat build-up. Furthermore, if water does sneak its way in, it can take much longer to dry those puppies out.
But, things are changing these days. Thanks to modern advancements in waterproof materials and design, we have footwear options that are increasingly versatile. Products that feature GORE-TEX® or eVent® membranes will offer waterproof performance and with varying degrees of breathability to keep you comfortable in a wide variety of conditions. Developed specifically for footwear, materials like GORE® SURROUND® and GORE-TEX® Performance Comfort are among the most breathable options with the latter designed for those high-intensity activities where breaking a sweat is the name of the game.
While strides have been made in creating footwear that is both waterproof and breathable, no shoe or boot will be a jack of all trades that performs perfectly in every situation. You will have to choose footwear with a balance of features that suit your needs and comfort preferences. Maybe you don't mind a little water between your toes and value quick-drying performance above all. Maybe you have a couple shallow stream crossings on your trail and a waterproof boot is just what the doctor ordered. Perhaps you're planning on some winter hikes with cold temperatures and snowy terrain. In that case, footwear without adequate waterproofing is downright irresponsible.
The cold, hard reality is that your feet have a good chance of getting wet at some point on your adventure. It's not surprising to find a hiker sitting on a rock dumping a puddle out of their shoe after a misstep or surprise storm. And many of us have had the pleasure of drying out our shoes by the fire. It's all good. Weigh the costs and benefits of breathable versus waterproof materials and as always, use your best judgment to maximize your comfort and enjoyment out there.

Underfoot
Do you know what lurks in the depths below?
What lies between your foot and the terrain can make all the difference
In short, you're either going to go with leather, synthetic, mesh or a combination.
INSOLE: Sometimes called a sock liner or footbed, the insole is the piece that sits right below the sole of your feet. These are either soft and flexible, or more rigid for greater support. Some are more ventilated than others, but most will do a good job at wicking moisture to keep your feet and/or socks dry. Almost all insoles are removable so you can take them out based on your comfort preferences, take them out for washing and drying, or even replace them with aftermarket or custom orthotic inserts.
MIDSOLE: This is the part that determines the stiffness/flexibility balance, and is also where most of your cushioning comes from. Midsole construction usually consists of EVA (ethylene vinyl acetate), PU (polyurethane), or a combination of the two. EVA is the soft, squishy, lightweight variety of foam that provides shock absorbing cushion. In contrast, PU is much more stiff and desirable for its supportive and durable qualities. Most footwear integrates both materials to give you a smooth creamy ride, mile after mile.
OUTSOLE: This is where the rubber meets the road. Err, earth. Outsoles come in many different forms as different rubber compounds result in various types of performance. Softer compounds will flex more but wear out faster while hard ones will be the opposite. Sticky rubber grips rock like a champ, and there is even rubber that grips ice and cold ground better than others. The sole pattern of a hiking footwear will have lugs facing various directions, all intended to help grip as you walk up, down, left, and right. The deeper the lugs, the greater the surface area to grab onto the ground.
SHANKS: No, not the kind that you whittle from a toothbrush, and not the thing your brace-faced cousin says when you compliment her. We're talking about a layer of plastic or metal sandwiched between the midsole and outsole that protects the bottom of your feet. You'll never see them, but shanks can extend through half, 3/4 or the full length of the sole. The longer the shank, the stiffer the boot.

The Fit
Make sure they fit juuuust riiiight
Poor fitting footwear can result in discomfort and injury, so try them on first
Just like any other sport, including basketball, football, tennis, and even ice hockey, what you wear on your feet can make or break the experience, and either enhance or compromise your performance. At the end of the day, you need to find a shoe, boot, or shoe boot that fits well with your foot and your comfort preferences. Your footwear should fit snug, but not too tight. The only way to find your golden slipper out of a crowd of potential suitors is to try 'em on and find what feels best on your feet. Oh, and make sure you wear a pair of socks you would plan on hiking in while trying stuff on. And if you are at a Moosejaw shop, ask the staff if you can try on a weighted backpack as well when trying on hiking footwear.
NOW GET OUT THERE ALREADY
If you're not comfortable, then your trip won't be either. Some hiking footwear needs a longer break-in period than others but if your feet are so upset on the first try-on, it's likely they won't get better after a month of hiking deep into the backcountry. Listen to what your toes are telling you and try a different pair, get another recommendation and when you find the ones for you, you'll know it. Then start breaking them in before you set off on the big adventure.