The BEST Winter Running Shoes of 2020

shoes winter running

Alright, so.  You're running outside this winter. Maybe your house is full of kids on school zooms shouting about the structure of a fictional story? Or your husband takes really loud phone calls in the living room, even though there are other rooms in the house WITH DOORS, about that new packaging his company is working on?

Do these examples seem oddly specific?

We get you.

But, if you're going to run (or walk outside), having the right gear is pretty key.

So, here's my round up of the winter running shoes we've got in stock at Lively.  Please note that I'm not a cold-feet gal (possibly a cold-heart gal, given me openly mocking my husband above), so I frequently run in regular running shoes with wool socks. That's always an option! These are just next level options:

1. On Cloud Waterproof. This shoe is probably our best seller of all the shoes we sell. It's lightweight, flexible, so comfortable, and not terrible to look at. The waterproof version is amazing. You can't even tell. It doesn't have a stiff feel to it at all, just as flexible as the original On.  This is great for walking or shorter runs. It doesn't have a grippy outsole, so pair it with Yak Trax or run with caution.

On Cloud waterproofOn cloud waterproof in blackon cloud waterproof in pink

2. Hoka Challenger ATR 5 Gore-Tex All the Hoka cushioning, but with more bells and whistles! This trail shoe features a strategic lug pattern for smooth transitions and a soft ride. Complete with a Gore-Tex waterproof bootie, this all-terrain shoe lets you run your best in every season. The Challenger ATR 5 Gore-Tex takes you everywhere no matter the conditions. It works equally well for winter walkers and commuters, too.

Hoka Challenger3. On Cloudflyer Waterproof. Yes, yes. Another On running shoe in the mix! But this one is more of a supportive shoes (what we might have called a "stability shoe" when that terminology was still in use). Great for people who need a little more rubber for heel impact and longer runs. Waterproof and snuggly for all!

cloudflyer oak park

4. Altra Lone Peak RSM. This shoe is weirdly cute, which I don't always say about an Altra. The "RSM" in the name stands for rain, snow, mud because this shoe is ready for them all! It has a breathable but protective upper, grippy outsole, and the traditional Altra foot-shaped form and zero drop design.

Altra Long peak

5. Saucony Peregrine IP. Water-resistant upper, and Vibram outsole for insane grip. I also feel like you run 2x faster when you are wearing all-black shoes #science.  


Saucony Peregrine

6. On CloudVenture (Waterproof and otherwise!). There is a reason we carry so many shoes by On Running, I promise. If you haven't tried them before, come on in and try a pair! They're great. These three models are all trail shows so they are a little stiffer than the Cloud because of the rock guard feature. And the CloudVenture waterproof is waterproof, so that's perfect for Chicago running!

On cloudventure


We have tons of other shoes, great warm socks, and all the winter running stuff you could ever want! Come on in for regular shopping, or shop online and take advantage of our free local delivery and easy return policy.



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