10 Top Picks for Winter Walking Hats

For over a decade I wore a Sub4 hat for most of my walks except in summer. It was stretchy and couldn't be blown off my head. It had a bill to shade my eyes from sun and rain. It had subtle ear covers to keep my temperature-sensitive lobes warm. It had a ponytail hole for my hair. It breathed well enough to wear in warm weather up to 65F and was warm enough down to 30F. Alas, it was discontinued when the owner of Sub4 decided to retire. What could possibly replace such an ideal hat?


Beanie or Stocking Hat

Red Stocking Hat Beanie

Anthony Rosenberg / E+ / Getty Images

What's wrong with a plain old beanie or watchcap, you ask? I will grant that they work well for night walks when you don't need a bill to shade your face from the sun, although I also like having a bill to guard my face from the rain. If you wear glasses, you may understand that well. In my youth, I knitted lots of stocking hats. It's Knitting 101. You can find or make beanies in any fabric you prefer, including wool and polar fleece.


Ponytail Beanie

Pony Tail Hat by GoneForaRun
Courtesy of Amazon.com

My biggest problem with beanies is that most of them don't have a ponytail hole, so that was a problem for the many years I had a ponytail. Thanks to online shopping it's easier to find a beanie that has a ponytail hole, in a variety of designs, such as those at ​Peekaboos-hats.com.


Fleece Cap

Windproof Fleece Earflap Hat with Visor
Courtesy of Amazon.com

A cap like this is made for winter running and walking. The microfleece earflaps and neck drape will help keep your ears and neck warm. It's windproof so the chilly winter blasts won't affect you. I like having a bill to shade my face from sun, wind, rain, sleet, you name it. This one has a great feature—the ponytail hole in the back is wide enough that you can wear the hat backward and see through the hole. Now you've got a balaclava for when you need it!


Visor Beanie

Binmer Visor Beanie
Courtesy of Amazon.com

A visor beanie will keep your head and ears warm while shading your eyes from sun, rain, and snow. I also like to have the bill when I am using the hood of my rain jacket, it keeps it in place. Many manufacturers have put them on the market in a big variety of colors and fabric. If you have long hair, look for one that has a ponytail hole.



Buff - Reflective
Courtesy of Amazon

I carry a Buff with me walking in all seasons. I can use it as an ear warmer over a billed cap. Or I can wear it as a neck gaiter, a beanie, a balaclava, a bandanna, you name it. The basic Buff comes in lightweight microfiber and is easy to carry in a pack just in case you need it. They also have models with a reflective stripe for night safety and models made with polar fleece or wool for extra warmth. Having one has saved me from cold ears or sunburned noggin many a time.


Turtle Fur Earflap Hat

Turtle Fur earflap hats have lovely wool knit outer designs and are lined with cozy microfleece Turtle Fur. That keeps the itches away from your head if you are sensitive to wool but like its natural insulation qualities. They come in a variety of colors. The ties will keep it from blowing off your head in a winter gale.


Trapper Hat

Outdoor Research Baltic Trapper Hat
Courtesy of Amazon.com

Full-on Fudd. This is the hat that would make my husband disown walking with me. But I bet it keeps your ears warm! What could be cozier than wool plaid flannel lined with fleece or even faux fur? You can button the flaps under your chin or button them up on top of the hat when you don't need them. You'll get that wascal wabbit!


Beard Beanie Hat

Beard beanie

Photo courtesy Amazon.com

Want to keep your chin warm as well as your ears? If you don't mind the fashion statement, this style will work. As a gal who had laser hair removal to ensure I didn't have a mustache and whiskers, I'm not going this direction for a hat. But take a look at different models, you can rock a look from Santa to Duck Dynasty or barbarian.


Shoreline Fleece Ball Cap

Like spotting an amazing guy on a crowded dance floor, I spied this and thought "it could be the one!" This windproof, moisture-wicking microfleece hat has an ear-covering flap you can wear up or down. It has a ponytail hole at back and a nice bill in front. I bought the Small/Medium but it is a bit tight, and they are sold out on the large size. Alas, the ear flaps don't fit as closely as I like, so it's not perfect. And my husband immediately blurted out, "You'll catch that wascal wabbit!" Maybe if I hadn't ordered it in red...


The Discontinued Sub4 Extreme Cold Hat

Sub4 Extreme Cold Hat

Wendy Bumgardner 

This is the standard by which I judge all winter walking hats. I appear in it on my walks around the world. Istanbul, the Eiger Trail, Denali National Park, Canyonlands National Park, Nazareth, Munich. I am putting one in a safe deposit box against the day I lose both of the other two I own. Sorry, not sharing!


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