The Best Running Gear for Your Long and Chilly Winter

As an iPhone owner, I am still pretty devoted to my Beats Fit Pro (9/10, WIRED Recommends), but even I admit that it's hard to spend more than $100 on a pair of headphones whose only purpose is to stick to your head and get crusty with sweat. Right now, my favorite out of the crop that I'm currently testing is the JLab Epic Air Sport ANC. JLab has consistently made some of our favorite affordable headphones. I have spent several weeks trying to run the battery out on these things with multiple walks and runs per day, but every day they continue to say “battery full” when I put them on. They come with around 70 hours of playtime, and the case can charge wirelessly (JLab's signature charging cable is included). 

They're rated IP66 against streams of water and are significantly thinner than some of the other earbuds I'm currently testing. For someone whose left ear is determined to spit out almost every earbud on the planet, JLab's Cloud Foam ear tips fit securely and well. I hate, hate, hate fidgeting with an earbud midrun. Everything you wear should help you, not irritate you.

The rule of thumb is to dress for running as if it's 20 degrees warmer than it is. For example, if it's 40 Fahrenheit degrees, you want to dress like it's 60. On those days, I like any leggings that are high-waisted or have a drawstring, so they don't fall down, and are made from compressive and durable fabric, like Lululemon's Fast and Frees ($98), which have reflective details and come in a few inseam lengths for short-legged folk. 

Once the temperature drops, however, the leggings slowly get thicker. Right now, I'm reaching for the Patagonia Pack Out tights. They're technically a hiking legging, which means there's a crotch gusset for additional mobility (I can't be the only one who loves a good crotch gusset). They're thick and insulated and have a wide waistband so they don't roll over. For below-freezing days, I have a pair of these Smartwool sport fleece tights ($140), which have a wind-resistant panel on the thigh.

Layering in the winter is a complex puzzle. What I wear depends on how long I'll be out and what I'm doing. A long, slow run with friends? I'll probably put on a breathable puffer jacket or a fleece for a glorified walkie-talkie. Short, fast intervals? Probably a wicking top under a water-resistant shell. But no matter what midlayers or shells I'm wearing (or not), I'm probably wearing a base layer. I've had one of these Smartwool shirts for years, and it still holds up.

Here I will offer you my second layering cheat code for free: Are you stymied over which jacket to wear? Save yourself some trouble and get a vest. A shell doesn't seem quite warm enough? Does it seem just a little too warm to put on that full-sleeved fleece? Enter vest, stage right. I particularly like this light, sleek, and stretchy one ($235) from Ibex, which is PFC-free and packs down small enough to stuff into my running pack. It also looks good enough to fit under my wool coat on days when it's just a little too cold

If it's around the 30s or 40s, any hat or headband will do. But when the temperature sinks lower—if you're still going out, which I might not be—you have a few options. Even an hour or two in sub-20 temps might be enough to give you painful frostnip or frostbite on your nose or ears. I'm also prone to cold-induced asthma, and I appreciate having something to cover the lower part of my face and help warm the air before it reaches my lungs. 

I prefer natural fibers, but I make an exception for this balaclava. The fabric is very soft, so you can wipe your runny nose and drool all over it as needed and it won't scratch your sniffly, snotty face. A hinge makes it very easy to pull it on or off your face as needed. It's also UPF 50, so it will protect you from the sun. 

This is the year we stop caring about “looking good” or even “looking normal” and embrace wearing horrible sunglasses not only while running but while picking up our kids and while walking to happy hour at the bar. 

Tifosi consistently makes some of the most durable and affordable specialized sports sunglasses. The Vogel SL are Tifosi’s running pair, and they have everything you want in sport sunglasses—hydrophilic grips on the nose, light and flexible arms, and big lenses that cover most of your face. They're not polarized, which could be an issue if you run in places near water or on snow with a lot of reflective glare. But if you're just going out for a couple of hours on the weekend and tossing these in your car's console when you get home, these are fine. 

These knit gloves have a bit of a cult following in Portland, Oregon, where I live. They have three layers—a rubbery nylon exterior, a waterproof membrane, and a warm merino wool lining—and they're expensive enough that I cried when I lost one (then immediately bought another pair). They fend off ice and rain and keep your hands warm when you walk out the door and your hands feel like they might turn into icy appendages bolted onto your body. 

Once you're a couple miles in, they vent heat when you've started sweating and are ready to strip everything off. They're also light and have little grippy pads on the palms that make them suitable for biking and hiking as well. 

I really like Nathan packs. They're small, simple, versatile, and last forever—I had my previous Nathan pack for years without noticing any wear on it (it did get a little smelly). Since I run (very slowly) and for long distances, mostly alone, I very rarely go without a bag of some kind. As the name implies, this one is small enough for short solo hikes and mountain biking excursions while large enough for a tiny hydration reservoir, some snacks, my phone, hat, and gloves. I also like the color!

If you're just running a few miles every other day, you probably don't need fancy socks with a lot of features. (If you do, we have a great running sock roundup here). These are the printed versions of Zensah's compression socks, which are our favorites. They have a seamless toe, added heel protection, and silver-infused fabric to combat stink. I also like crew-height socks when trail running, because the higher sock keeps me from kicking pebbles or dirt into them. The cool tan lines are just a bonus.

Maybe you don't really need a headlamp so that you can see. Maybe you need lights so that car drivers can see you. A safety vest ($9) works great, but I also have a drawer with a box filled with an assortment of miscellaneous lights for when dusk starts to fall. They're waterproof, have a 40-hour run time, and recharge just by sticking directly into a USB port. Most important, they're light and have a clip, so I can stick them anywhere on my clothing—pockets, lapels—and not have to worry about fitting them on top of my hat, earbuds, or whatever else I'm wearing on the other parts of my body. 

You'll have to experiment to find which snacks keep you fueled without upsetting your stomach. Highly processed goos and jellies tend to give me diarrhea (sorry). These cookie bites are pocketable and come in separate bites so that you don't leave half-eaten bars in your pockets when you throw your jacket into the wash. They're sweetened with dates and cacao and are tasty enough that even my 5- and 8-year-old will eat them.

The worst problem with winter running is stiffness and getting injured. If you don't start slowly and give yourself enough time to cool down and stretch, your muscles can really suffer in cold climates. A few common ailments include shin splints or plantar fasciitis, which you can usually avoid by starting slow, warming up and cooling down, stretching, and upping your mileage gradually.

If you get unlucky enough to acquire some kind of chronic ailment, I recommend seeing a physical therapist who specializes in running. But I would also recommend stretching and getting a small, cheap, hard, rubbery lacrosse ball. Just spend a few minutes each day rolling out the muscles in your calves, thighs, and feet. It's like using a foam roller but smaller, easier to transport, and better for targeting small muscles.