The secret to enjoying a winter hike (or other winter workouts) when the temperature is in the single digits is dressing properly for the conditions. While your normal clothes are enough for a 15-minute stroll through a city park, for a long hike in frigid conditions, you'll have a much better experience if you dress appropriately and stay dry.
A Hat Is a Hiker's Thermostat
It's the easiest piece of clothing with which to modulate your body heat, but also one that hikers stubbornly ignore. Keep a hat on when you're cold, off when you're hot, and buckled down tight when the harsh winds blow. A hat like the Women's Textured Fur-Trimmed Hat ($31.50, part of the Eddie Bauer Semi-Annual Sale) can help block out the midwinter sun that lies so long just above the horizon.
In extreme weather, especially with wind, you can beef up your head protection by donning a balaclava (not to be confused with baklava, the delicious Greek dessert that could serve as emergency food if brought along on a hike). The SmartWool Balaclava ($31.96, part of the Backcountry Semi-Annual Sale) is made from merino wool that keeps its temperature-regulating properties even when wet. It's hard to say the same for cotton. In winter hiking, cotton is your enemy; it gets wet and stays wet, ruining any insulating properties by turning a chill into a freeze.
Layering Keeps Your Core Warm
Wearing several layers that you can don and remove as your body temperature dictates is the way to go. Start with a lightweight synthetic like the Merrell Men's Ascendancy Half-Zip Pullover ($24.49 via coupon code "SAVE30", with free shipping), which will wick moisture away from your skin and allow it to evaporate, keeping you dry and warm.
Your second layer of clothing should be made of a heavier yet breathable material, like the Route 66 Men's Fleece Hoodie Jacket ($22.99 with free in-store pickup). For an outer layer, try a rain jacket to keep out both rain and wet snow, and to block the wind. A fabric that allows perspiration to escape while remaining rainproof is best. The L.L.Bean Women's Cloudburst Rain Jacket ($99.99 with free shipping; bundled with a $10 L.L.Bean Gift Card) is a good selection.
I usually only wear two bottom layers, since my legs are doing almost all the work, and thus generating the most heat. I first suit up in a pair of long underwear. Ladies might like the Women's Fleece Lined Thermal Underwear Set ($12.99 plus $2.99 for shipping, a low by $1). For an outer layer, consider Nike Men's KO Fleece Pants ($41.25 with free in-store pickup, a low by $5), which have moisture-wicking technology to help keep you dry and warm. Some hikers prefer rain pants to match their rain jacket, but I've found them a bit too hot and annoyingly noisy while walking through picturesque winter landscapes.
To keep my lower legs and feet dry, especially in muddy or snowy conditions, I highly recommend high gaiters, which wrap around ankles and calves and hook into the top of your boots.
Put Your Best Foot Forward
The most important piece of gear, in my opinion, is footwear. Any light hiking boot or running shoe will suffice on dry urban trails, but if you are bound for the backcountry, where you might have to scramble across creeks or wade through snowbanks, you would be well-advised to invest in a pair of boots. A good pair might last most of a lifetime, so they're a worthy investment.
Leather boots can be waterproofed with a coating for winter and wet conditions, and breathe easily enough to keep you from getting cold feet. Consider L.L.Bean Men's Gore-Tex Ascender Hiking Shoes ($99.99 with free shipping; bundled with a $10 L.L.Bean Gift Card), which have a waterproof upper and inner lining.
Along with a good boot, socks can make the difference between a happy hiker and a miserable one. Here too, think layering. Start with a light, synthetic liner sock like the two-pack of the Bridgedale CoolMax Liner (from $17.96, part of the Backcountry Semi-Annual Sale), and then pull on a pair of the Merrell Women's Fluorecein Socks ($13.30 via coupon code "SAVE30", with free shipping), or other synthetic or wool hiking socks to keep your feet warm even when wet.
If you're heading out in severe conditions, think about layering your hand wear, too. I'd put on glove liners to start with. Cover these with some mittens — fingered gloves expose more of your hand to the air, and are therefore less warm. Slip on a pair of mittens and you're ready to go.
Sure, you may end up looking like a cousin of the Michelin Man once you're all bundled up, but that's a small price to pay for a full day of hiking through a winter wonderland. Don't let the weather trap you inside; there's a whole world to discover when snow is on the ground, and ice and wind have turned even the most humble pine tree into something glittering and new.