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 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?
I spied this for sale on the Roadrunner Sports web site and ordered it. It is waterproof and windproof. It's lined with microfleece. However, the ear flaps come down too far and there is no ponytail hole in the back. The hat cinches to your head with a drawstring but my hair is too slick for that to work well. As a result, the hat keeps creeping up my head and I have to keep pulling it down. The earflaps don't fit as close to my ears as I am used to, so there is air flow around your ears. That makes them feel cooler than I want. Meanwhile, it has a high "Elmer Fudd Factor" that makes my husband not want to be seen with me. This hat may work well for you, but it's a miss for me.
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. I think my biggest problem with beanies is that most lack a ponytail hole. If you don't have a ponytail, this isn't going to be a problem for you. On the plus side, you can find or make beanies in any fabric you prefer, including wool and polar fleece.
4. Sporthill Energy Beanie
This soft and stretchy beanie is made from polyester and spandex in SwiftPro windblocking fabric. It has a feature I consider essential -- a polytail hole in the center of the back. It has extended ear flaps that are not Dumbo-sized. Although it doesn't have a bill, this hat comes closest to my beloved, now discontinued Sub4 winter hat. It should layer well under a hood. Manufacturer's Site
Want to keep your chin warm as well as your ears? If you don't mind the fashion statement, this will work. I like the bill on the cap. It's made of recycled cotton and polyester. The beard is handknit. The drawback is that there is no ponytail hole. Also, 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.
I carry a Buff with me walking in all seasons. I can use it as an earwarmer 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.
Embrace the earflaps! This Turtle Fur model is hand knitted in Nepal, with lovely wool outer designs lined with cozy microfleece Turtle Fur. While my husband doesn't think Elmer Fudd-style earflaps are cool, he thinks Sherpas are the utmost in cool. This hat supports local artisans in Nepal. They come in a variety of colors. The ties will keep it from blowing off your head in a winter gale.
8. Trapper Hat
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 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!
Like spotting an amazing guy across 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...
10. The Discontinued Sub4 Extreme Cold Hat
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!