Really, layering is the key to a successful commuting attire. And never are your layers more important than in the winter when the chill from outside can penetrate your bones while the sweat from your biking effort can drench you from the inside. Ideally, investing in some quality wool items is the best way to go as not only does wool insulate while wet (key in our damp, moist PNW winters), but it is also breathable and dries relatively quick. Good items to get in wool are baselayers, knickers/pants, hat, and socks. Also good are other synthetics. Pretty much, stay away from cotton. The only time cotton is a good baselayer is when it's in the form of a tank top during the summer months - and even then it's prone to leave you with that clammy feeling.
Anyways, this is just a little diagram of my fall/winter/spring bike commuting attire:
1: A HAT (worn under a helmet). A short brimmed hat can do wonders for your bike commute and damn are they stylish and a very personal expression of you as a biker. Not only will they insulate yournoggin in the cold, but they'll shield your eyes from the sun and the potential downpours. I love me a good wool tweed cycling cap and a local company, Showers Pass even makes one that looks like tweed but is rain repellant and aptly named, the Portland Hat. Personally, I sport my orange racing cap that was made exclusively for my team my local seamstress Caroline at Little Package.
2: QUALITY BAG One that isn't cumbersome on your ride, nor does it shift, pinch your back, and it must keep rain, dirt, and road grime away from your cargo. Personally, I sport a large Timbuk2 bag.
3: BASE LAYER Basically, in the winter I layer by wearing a t-shirt or tank top (try to steer clear of cotton) and then a lightweight fleece or wool sweater. You can also get away pending on the chillyness, by adding some arm warmers. I find that I really don't need to wear a big bulky coat and nor do I want to wear the long sleeved shirt that I'll have on at work since I'd sweat through it on my ride.
4: WIND/RAINLAYER This is a very important part since this is the main ingredient in what shields you from the elements. I happened to pick up the other year a very nice Patagonia jacket that is not only a raincoat and a great wind jacket, but it also breathes and is made out of a stretchy material that isn't too bulky. As well, it has a nice slim fit which works for the biking profile. Big rain coats are fine, but sadly most of the basic rain coats you're gonna find out there are going to make you feel as if you are riding your bike covered in saran wrap. True, you may stay dry... but your innards are sweating out. Also, whatever coat you wear on the outside the most, you should make sure that it's not black (winter's are dark and visibility is poor ya'll) and even if it is a lighter color (please no highlighter yellow folks, it hurts my eyes) pick up some reflective tape at the store and make sure you can be seen.
5: GLOVES Personally, I'm still searching for my favorite winter riding gloves. I've noticed out of everything, my fingers tend to get really cold really quick. But, whatever you get, make sure it's going to be windproof at least on the outside where you hands get the brunt of the wind, that they provide grip on the handle bars, and do well when it's wet.
6: PANTS Oh pants. How I love thee. How I despise thee. Wool, is a great option for the reasons mentioned above and it's pretty easy to get out to goodwill and buy an older pair of wool pants to make into knickers ideal for riding. But really, I own like maybe one pair of wool pants and I hardly ever ride in them. What do I own? ... cotton jeans and slacks. On dry and cold days you can think nothing of just rolling your pants legs up to your calf, mounting that bike and being on your way. However, on rainy mornings... this isn't the best idea as your pants will not only be soaked from the rain, but also all the grime coming off the road. Really, the best option is investing in a cheap pair of packable rain pants - but I HATE riding in rain pants. As well, I hate when your pants stay dry in rain pants but all the rain rolls off your pants into your shoes and socks, soaking them. Last year I devised a stirrup system based upon fastening clips from my rain pants around the bottoms of my shoes to keep my socks dry... but found the clips had a hard time gripping my rain pants well. I think this year I'm just going to accept a damp bottom half and ride in long spandex and old shoes and socks that I can take off upon entering work and pray that the rains have ceased by my ride home so I don't have to put them back on. Worst case though, you just have to bring shoes and pants and socks with you (which is why I have a big bag). If you do this often enough, you learn to just leave a pair of "work shoes" at work.
As well... I have worn through the seats on several pairs of jeans. I recently picked up a "pants version" of my favorite pair of Patagonia shorts that have a reinforced back side, so I plan on putting them to the test of how well they hold up for mile after mile on the bike seat.
7: TALL SOCKS Just perfect for those jeans rolled up to mid calf. Make them fun. My personal favorites last year were my Obama socks , but anything goes. Wool or other synthetics are a good choice as it will keep your feet and legs warmer and dryer. Smartwool makes some great tall socks that are a lot of fun.
8: STURDY SHOES Like I previously said... I try to minimize the amount of stuff I have to carry with me and packing in "work shoes" everyday gets old real fast. As well, I know some people love to ride in their cleats and clip in, but... once again... that requires normally another pair of shoes for work and what if you have to run an errand on your bike? That's gonna be you, click clacking through the grocery store. I proudly admit, I am a fan of baskets on the pedals. Not only can you normally just wear the shoes you'll be wearing to work... but you can also size your baskets to fit your wide boxed or pointy toed boots. Sadly though, I've found that my baskets wear and scratch my shoes just a little, so I started wearing "boot coozies" for my favorite shoes. Boot coozies are just cheap big socks are large enough you can wear them over the toe boxes on your favorite shoes to limit the scratches or cut the socks to fit. Similar to calientoes, but cheaper.
If you are so inspired to see a little bit more top of the line stuff as in what the "industry" is calling commuter bike friendly fashion, watch this little video of the Momentum Bike Fashion show that the bike magazine "Momentum" held at this years Interbike in Las Vegas.
Or if you really feel like being the cycling dandy, you can go spend a few thousand dollars on this Rapha cycling suit.
Which, much like all of the other swell Rapha stuff, I'm waiting for them to make women specific cuts - but, I guess that just helps me in saving my money till they do. Really, you should check out Rapha. Their US HQ are in Portland and they make a lot of really really nice, really really spendy cycling clothes (and have some great bike inspired photography).
Anyways, less is more and you really don't need tons of great gear to get to work on your bike and stay dry. However, if you're one of those seasonal riders, go ahead. Drive, take the bus, take the max. I'll gladly take less people crowding my bike lane and spraying road rain on my face.
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