Your first step in winter is safety. Your second step is staying both warm and dry. In days of yore winter meant wool and down. Today, it means warm and wicking fleece to manage both heat and sweat. Layer yourself top to bottom, inside to out with wicking and breathable fabrics.
2. Polar Buff
A Buff is a seamless tube of fabric that can be worn as a hat, a neck gaiter, a ski mask or balaclava. You may have seen contestants on Survivor using their Buffs in many different ways. A polar Buff has a band of microfleece at one end for extra warmth. It makes a great balaclava to cover the head, neck and chin. You can layer it under another hat. The Buff packs up very small. It is easy to carry one in your pocket, purse or pack to use when you really need it, and stow it once you have warmed up.
When the temperature falls below 40F, I like to switch to a microfleece hat. It has to have ear coverings, as my ears get very cold. The L.L. Bean Wind Challenger Baseball Cap provides good coverage for the ears without looking like a hunting cap. I like having a bill to keep the sun and rain out of my eyes while walking. The microfleece insulates and the Windbloc stops the wind from penetrating, yet it is breathable so moisture is wicked away from your head. This hat also has a water-repellent coating. I like that it has a ponytail hole at the back. You can find similar models from REI, Lands End and other vendors.
Polyester microfleece is cozy and soft, yet wicks away moisture and insulates on the cold walking days. When the temperatures dive below 40F, I wear a microfleece pullover under my waterproof jacket as my insulating layer. The pullover does double duty at home, as I love to slip into a microfleece pullover after a winter walk.
6. REI Woodland Fleece Vest
Your base layer for cold walking must have high wicking capabilities and provide some insulation. One such choice is the REI Lightweight Crew Shirt (Buy Direct). I like that version because it has handwarming sleeves.
When it gets really cold, your legs will also want insulation. Wear these wicking long johns under your walking pants. The REI Lightweight Long Underwear Bottoms (Buy Direct) fit snugly for ease of layering under your walking pants. But others may want the extra warmth of Smartwool versions (Compare Prices).
Slip-on cleats for your shoes or boots. I keep a pair of these in my car throughout the winter for those times I have to trek on icy or snowy sidewalks. They slip on over your shoes or boots and slip off once you are safely inside.
10. Yaktrax Pro
Chains for your shoes. Keep these handy for trekking on icy or snowy sidewalks. They slip on over your shoes or boots and slip off once you are safely inside. Yaktrax uses coils rather than cleats or spikes. The Yaktrax Pro has a velcro strap across the top of the shoe for extra security.