Toe Cozy: Hiking with Seema in the winter is fun (when is hiking with Seema not fun?), and you'll be in good hands. Wait until you see the neat things her hair does!
Most everything that you need will come some from trial and error.
Start small, stay away from cotton, work out a layer system, and just go. I'm sure that there are some local hills that you are very familiar with, so start there. Learn map and compass basics: one good way to strt the learning process is to take them out on every hike as you start. Orient the map with your compass, visualize your route, and pay attention to features that you will pass. The more you use it, the better you will get.
Knowledge comes fast and there are 2 ways to gain it:
1) the hard way: head out, and you'll see what you need. Taken to the extreme, it would take you about 3 steps when barefoot to realize that you needed boots
2) the expensive way: buy it, try it, replace it.
I prefer method #1. Sure, you might suffer a bit, but you will quikly find what you REALLY want and need. Pay attention to what your hiking partners use, and don't be afraid to ask questions during the hike.
OK, a long list follows (you've been warned!)
Here is a gear summary of what I use for a typical day hike:
General comment on clothing: the most important piece of gear that you will need. Layering is key, starting with a good polypro or capilene layer and building from there. Focus on hand, head and eye protection: you will want to be able to cover every exposed inch of skin when required to prevent frostbite. With proper clothing, you will find that you stay quite comfortable while hiking. With that said:
Base Layer: I start with a midweight (or lightweight if warm) polypro long sleeve top and bottom. I also have a poly/mohair shirt that I like. As it gets colder, I put a T-shirt on (REI poly). I also carry a Sportif Windstopper fleece vest (the back is regular fleece). It goes on often before (or instead of) my shell
Hands: Poly liner GLOVES under Fox River double ragg wool MITTS under OR Gore-Tex overmitts. I carry fleece and Gore-Tex liners, have used them infrequently, but I always carry them!
Socks: Smartwool Expedition weight over poly or Thermax liners. Also use Wigwams and Thorlo, but Smartwool are #1 to me. I don’t use VBL, but some folks like them.
Gaiters: OR (Outdoor Research) Expedition Crocs. Try them on over your boots and hiking pants before you buy them. The Expedition Crocs are the only Crocs that fit my short stubby legs
, but I suspect the regular Crocs will fit you fine. Gaiters are real important for dryness and warmth.
Wind Pants: I don’t get cold easily, so only use Marmot Precips. I am looking for a good pair of waterproof/breathable full zip pants, but have not been lucky (you won’t have that problem – they just don’t think guys like me hike)
Shell/Jacket: Sportif 3 ply Goretex shell with hood. Cabelas Down Jacket sized to fit over my shell (like a TNF Nuptse)
Hat/Balaclava: OR Peruvian windstopper hat and OR Windstopper Gorilla balaclava (I’m not sold on this one yet). I also have a Seirus neoprene/fleece facemask that I use often
Eye Protection: Smith Double lens goggles. Julbo Sherpa glacier glasses. I coat both with Cat Crap to keep them from fogging. I wear my contacts in winter almost exclusively.
Boots: I love my Koflach Degre's but spent quite a few years hiking with leathers before I could afford them. If doing day trips, stiff leathers (steel shank) will be fine to start. Light day hikers are not recommended. Make sure that they are waterproofed well (I use sno-seal)
Crampons: I've never had a problem with my Grivel G-10's New Classics. I bought my recent pair 6 years ago. They are a modified strap type and fit a wide variety of boots
Snowshoes: I've not seen many wooden snowshoes on the trail, but they would be excellent off trail. I really like my MSR Denali Evo Ascents and my Sherpa Khumbu Climbers. I carry a repair kit of some basic items, mostly pins, duct tape and cable ties.
Hiking Poles: mandatory IMO. They help you keep your balance, and are indispensable in helping you get back up if you fall (or end up in a spruce trap). Make sure that you swap to the winter snowflake baskets.
Water: I use an OR bottle parka for one of my water bottles, and stash the 2 others in my pack, near my back. I typically carry 3-4 liters on winter hike. You need to be very conscious of staying hydrated in winter!
Pack: Yes, you will need a pack to carry all this stuff. When choosing one, pay close attention to how you will attach your snowshoes and crampons. When they are not secured well, it will quickly be a source of frustration. I use a TNF Exocet, like it, but would love it if it had some internal frame system. Figure on 2000-3000 cu in.
That's the short list... It doesn’t get into the safety gear that you will want to bring (stove, 20F sleeping bag for every 2 people, etc), but at least it’s a start. There are many good gear lists available on the web.
As Nike would say: Just Do it. And as the Boy Scouts say: Be Prepared.