What to Wear
Many, many times, we find ourselves surprised by what other people on the trail are wearing. A lot of the time, it's obvious that people have no idea what to expect when hiking and treat a hike in the woods as if it were a stroll through the mall. So we're going to offer up some tips on what to wear to have an enjoyable experience in the midst of nature.
Hat: It's always advisable to wear a hat of some sort, ranging anywhere from a standard baseball cap to a wide-brimmed straw hat. A hat is good for two reasons: a) In warmer expeditions, it keeps the sun off your head (helping reduce dehydration and preventing sunstroke) and out of your eye (can't enjoy the view if you can't see); b) In colder expeditions, it keeps your head warm, and any schmo worth his salt can tell you, you lose most of your body heat through your head.
Bandana: And excellent alternative to the hat, it works well if you'll be engaging in activities where a hat may be cumbersome (rock climbing, rafting, etc.). Also a good choice for ladies with longer hair, as the bandana does a decent job of keep the bugs out of your locks.
Shirt: Believe it or not, I am a firm believer that any type of shirt will work. Old gym shirt, specialty hiking blouse, whatever. The important thing to remember is that your shirt must fit properly (not too short, not too tight). Sure, given the choice, I'll opt for some sort of moisture wicking top, but in a pinch, anything is just fine. Remember, if you're going to get wet (or sweat a lot), bring a back-up shirt.
Jacket: Use a jacket especially designed for the outdoors. They're usually waterproof, lighter to wear, and do a great job of keeping you warm. Avoid getting a heavy ski or winter jacket as your sole "camping" jacket because it'll be too hot for you during the rest of the year.
Sweater: A sweater is only really recommended for relaxing around the campfire or if you're taking short hikes away from the car or camp (< 1 mile). Usually, sweaters are heavier to carry and do badly when they get wet. It's better to sport the jacket on longer expeditions instead of a sweater.
Shorts: I can't stress this highly enough: NEVER wear cotton shorts. No denim, no cargo shorts. The reason is simple: if they get wet, they stay wet... for a long time. Only wear synthetic fiber shorts, or at worst, a cotton-poly blend, because they'll dry faster. And believe me, you will encounter frequent opportunities to get your shorts wet (rafting, hiking the Narrows, just jumping in the lake, etc.) Not to mention, they're lighter. Synthetic shorts aren't that expensive, so if you find yourself going hiking more often than you thought you would, buy a pair. You'll thank me later.
Pants: Unless you're going to invest in synthetic fiber pants (which may or may not be worth it depending on your Expedition patterns), I'll bend our rule of thumb and cautiously allow the use of denim. Because denim holds up well in colder weather and can take a beating in the backcountry, it can be just as effective as synthetic, and expeditions requiring pants due to colder temperatures probably won't provide an opportunity to get them wet. HOWEVER, if your travels take you to a place where you know it's going to rain and/or snow, you have to go synthetic. Denim will wick up moisture, even in light snow, and the last thing you want is to catch hypothermia because you're legs were wet and cold.
Boots: A good pair of boots is a hiker's best friend. When you're looking for a boot, you should be looking for something comfortable, waterproof, and supportive (preferably in the ankles). Also look for a good tread on the sole. If its got no grip, you're going to slip. One thing with boots: if it doesn't feel comfortable when you try them on in the store, no amount of "breaking-in" is going to help (especially if it's tight in the toes). It's one thing for a boot to be stiff, and another for it to be unwearable.
Hiking Shoes: This is what we usually sport. The hiking shoe (other names include: trail shoe, outdoor shoe, etc.) operates just like a boot, but is "low-cut," giving you greater range of motion in the ankle. That's extremely helpful if you're doing any bouldering or climbing. One other major benefit of hiking shoe over hiking boot is weight. Boots are going to be heavier than shoes and on longer days, that's going to take its toll. The downside is that shoes won't last as long as a good boot. And as always, check for a good tread.
Athletic Shoes/Sneakers: Good in a pinch, but usually only something in a cross-trainer. Basketball shoes aren't good because while they may offer ankle support, they usually have no tread (they tend to have flat soles for maximum grip on the court, which cause a lot of slippage on the trail). Running shoes also aren't that good, because while a select few may have a tread, the design of the running shoe doesn't provide enough support for any kind of hiking or climbing. If you are having trouble finding a comfortable boot or hiking shoe, find a cross-trainer with a good tread and leather uppers.
Sandals: Hiking sandals or outdoor sandals prove to be popular with some folks for all-purpose use, but I don't like them as an everyday option. They don't provide the necessary foot support for most terrains and leave your foot unprotected for ground level varmints. I would recommend having a pair of decent strap-on sandals with a good tread for specific cases (like hiking though water), but that's about as far as I would go with these. Flip-flops are NOT suitable for any conditions.
Gloves: I've found that different types of environments call for different types of gloves. The biggest factor with gloves is the temperatures they'll be used in. Sometimes, winter or ski gloves prove to be too hot outside of winter, while lighter gloves, or the popular finger-less gloves, don't offer enough protection in the cold. If you're going to commit to only one pair of gloves, I would recommend a pair of leather workshop gloves. They can usually handle most cold conditions and thick brush.
Mittens: Only to be used relaxing around the campfire. Never wear them on a hike. Use gloves instead.