I’ve been over (and under) dressing for winter running for years. It takes some trial and error, some sweaty days and some numb fingers as you dial in what layers to wear when.
This beginner-friendly (and slow-runner friendly) guide will help you get a head start so you won’t freezing your booty off this winter!
Note: This guide is based on my personal experience. It also contains affiliate links, which cost you nothing extra but earn Outdoor Beginner a small percentage commission if you do make a sale. Any links to REI, Amazon, or Under Armour are affiliate links. Other products linked are carried by my employer, Runners Roost, but I don’t get a commission or any other reward for posting them here. I’ve just tried them at work and really like them!
A good rule of thumb is dress like it’s 10 degrees warmer than it actually is.
If you’re dressed right, you should be uncomfortably cold for just the first few minutes (or first mile) of your run before warming up and feeling good. If you’re wet with sweat, you’re overdressed.
Other factors to consider:
How windy or precipitation-ey it is on your route. If you’re running in a more open area, it might be windier (particularly if you are on an exposed hilltop like a mesa). Windproof or rain-proof layers trap body heat, so you may need to only wear a light long-sleeve shirt or t-shirt under your jacket.
How sunny it is on your route. Running in the sun will be hotter than running in the shade or cloudy weather. Keep in mind if you’re in the city, the shadows of tall buildings may keep you in the shade the entire time. Same goes for a trail run in a heavily wooded area or canyon.
Whether the sun is coming up or going down. It’s going to get hotter as the sun comes up, and also significantly cooler once the sun goes down. And, you will likely need to add reflective gear or a headlamp to stay safe in the dark.
How hilly your route is. For most beginner runners, hills are both very hard but also typically walked. Consider whether you might get chilly while walking a lot of uphills (and add another layer if so). Or, if you’re doing a harder workout or know you’ll be running uphill a lot and exerting a lot of effort (see below), dress lighter.
How much effort you’re exerting. If you’re pushing yourself, that means less clothing is needed. The last thing you want is to get wet with sweat and stay wet; that’s a one-way ticket to being miserable. Note: Pushing yourself doesn’t mean that you’re running ~really fast~ or pounding out 10 miles. It could just mean you’re going to try to run all the way around the block with no walk breaks for the first time.
Layers are your best friend.
With all those factors to consider, there will be some trial and error in the beginning (or if you’re like me, at the beginning of every single winter). You’ll get the hang of things eventually! The most important thing to keep in mind is to dress in layers.
Start with a moisture-wicking base layer
This is the piece of clothing closest to your skin. You’ll be fine in cotton if you’re just starting out and aren’t outside for very long (ie you’re just trying to run a few blocks without barfing like I was). You might be a little uncomfortable, but you’re not going to have some catastrophic consequence (the saying “cotton kills” might apply to being out in the wilderness, but not for learning to run).
If it’s possible to purchase a base layer, look for something thin and highly breathable. Yes, thin! The layer closest to your skin is what wicks the sweat off of you and keeps you dry. Cotton isn’t particularly good at this, because it just stays wet, so you’ll feel chilled. Again, this isn’t an issue if you’re just trying to get around the block.
If you live in a place where it’s regularly below freezing and/or not very sunny in the winter, a long-sleeved base layer will be most helpful. You can re-use summer-friendly t-shirts or tank tops during the winter if you live somewhere sunny and run the risk of getting hot (like Colorado).
My favorite long-sleeved layers are:
- Smartwool Merino Base Layer (I own and love this one! And it’s 25% off as of 11/16/22)
- Rabbit EZ Tee Long Sleeve (incredibly soft – and stays soft!)
Add another layer as needed.
Once you’ve considered the 10-degree rule and the running conditions we’ve talked about already, decide whether you need another layer on top of the base layer.
This can be a hoodie, a fleece jacket, puffy vest, pretty much whatever you’re comfortable in or already have.

You probably won’t ever need a winter coat to run in – but if you’ve driven somewhere else for your run, it can be nice to keep that in the car to warm up when you get back!
Experiment with different combinations.
Some people can run in shorts no matter the temperature, but my joints get very upset if exposed below 45 degrees. I also get really hot and sweaty on my upper half, so switching to pants and short sleeves when it’s in the 40s has been a game-changer. If you’re wondering what took me so long, it was my preference for how shorts and long sleeves looked together.
I know I sound like a broken record, but this is another really helpful thing to experiment with as you learn what layers work best for you.
Use what you have.
Are cotton leggings not meant for sporty activities ideal for running? No. Did I wear the ~fashion~ leggings I already had from LOFT for most of my first runs? Absolutely.
I am in no way insisting that you have to go buy ALL THE THINGS. Technical fabrics are pricey, and I know everyone can’t just go buy a whole new wardrobe of things to sweat in. When you’re just starting out, use what you have and build slowly from there.

If you buy one thing, buy good base layers.
Moisture-wicking, quick-drying, technical fabric base layers are the best investment I’ve made. They make winter running so much more pleasant – getting (and staying) too wet and sweaty is SO much more miserable then just being too cold from under dressing.
Here is the link to my favorite one more time.
Springing for leggings is the next best investment.
I rocked those LOFT leggings for a long time because I maxed out at half a mile and wasn’t actually outdoors for very long. Once I got too cold and didn’t want my favorite leggings to get gross, I gutted up and spent $50 on insulated running tights. This seemed like a lot of money to buy something to sweat in, but they’ve lasted for years of near-daily use (I don’t run that often, I just wear leggings as pants a lot).
Leggings are harder to fit then shirts, so the best brand to get is the brand that fits you the best. I have two rules of thumb: Go for a name brand and get a pair specifically for cold weather. Normally, I love Target for cheap active wear. But in my experience, cheap leggings don’t stay up and I’m constantly pulling them up while I run.
Leggings that fall down aren’t always cheap, though, they may just not fit right. High-rise leggings or a pair with a drawstring are the best combo I’ve found for leggings that don’t move. If you have really straight hips like I do, a lot of men’s tights will have a better drawstring, which make them a great option as well!
Insulated/cold weather leggings will also make a big difference in staying warm. This doesn’t have to mean bulky – running clothing technology has come a long way (and that’s why we pay so much for it)!
Under Armour makes tights that are both really thin and very warm (with pockets). However if you trail run often, they aren’t particularly durable. I’ve ripped two pairs easily; once by just sitting down on a rock to re-tie my shoe (yep had to run with a hole in the butt of my pants) and the other time for a minor fall on a very smooth trail. If that’s not an issue for you, here’s their current selection.
If you do trail run and are looking for more durable options, try North Face or Salomon!
Don’t forget your head, hands, and feet.
Gloves are important. Your hands will be numb and you will probably be hating life pretty soon if you go out with your hands uncovered. I wear gloves if it’s under 40 degrees. You don’t need anything super thick – I love these thin, but wind-resistant, ones. If you do need something warmer, try a glove that converts to mittens!
For your head, an ear warmer or Buff is less hot than a hat, plus they accommodate a high pony or bun. I like using a Buff as an ear band when I’m running longer or faster (for me, a 10-minute pace). For windy or below freezing conditions, a more substantial ear warmer or hat can be helpful!

Non-cotton socks will keep your feet dry. Even if they get wet with snow! You can find synthetic material socks anywhere from Target to local running stores and REI. The latter will be more expensive, but will also last longer. My cheap socks from Target lasted about a year and a half, while my pricier Darn Tough socks are still going strong nearly a decade later. Feetures and Balega are other great options.
Consider higher socks (like a crew or “mini crew” height) for days under freezing or if your leggings aren’t long enough to cover your ankles.
The bottom line.
Dress like it’s warmer than it is. The 10-degree rule is a great starting point to figure out what works best for you.
Wear plenty of layers and don’t be afraid to experiment. There will be trial and error. If possible, invest in a moisture-wicking base layer shirt that isn’t cotton. Upgrade to non-cotton leggings next.
Don’t forget your extremities. Gloves, ear warmers, and synthetic socks are your friend!
One last thing: Safety.
It’s important to wear something reflective besides your shoes. Cold weather means shorter days, which means cars have a harder time seeing you. Consider a reflective vest like this one.
Bring a headlamp. The combination of questionable lighting and extremely questionable sidewalk quality in my neighborhood has made me a devotee of running with a headlamp. I run with a Black Diamond headlamp.
Best of luck with your trial and error! I mostly learned how to dress for running in the winter by wearing way too many clothes and getting too sweaty. That might happen you, too, but don’t worry – you’ll get to the happy medium eventually! Have fun out there.
Haha I’m with you re: not understanding how or why all these women’s hats don’t have a hole got a ponytail! That’s a requirement for all my hats for working out 😊
Right?! I’m with you. Maybe one day we’ll have ponytail hole for all!