The Gear Mistress Says...

Here is an-ever growing list of things that will make bike-commuting more palatable for the average newbie:

• Know your route: unless you like the sensation of being a scared bunny rabbit surrounded by wolves, then you should do a little research before you set out to ride to work. Look at maps online (google maps now has bike routes in beta; also check out bycycle.org; or download a pdf map from the city of Portland here)
• Dress appropriately: layer with materials such as wool, cotton, and technical fabrics. I personally hate fleece, so you're on your own with that crap. My personal faves are short pants (jeans that I have cut to mid calf so there is no interference from Le chain) with knee high wool socks, a long cut undershirt that will stay tucked into my pants and prevent the peek-a-boo ass crack breeze, a wool sweater+softshell jacket+rain shell if it is pretty cold outside. A good rule of thumb: when you first set out to ride you will feel a bit chilly, and then you will warm up. If you start out too warm you will be soaked with sweat, and then you will be REALLY cold when you get off your bike. Boo to that. Carry one of your layers in a bag if you are unsure, that way you stay less sweaty and have the option of adding a layer if you need to.
• always bring a hat/ear band+gloves. I seriously bring these with me all the time except in the extreme heat of summer, and even then I bring my INGENIOUS invention of Cheap Arm Warmers (take a pair of cotton/poly opaque tights and cut the legs right at the base of the crotch, and then cut one large and one small hole for you fingers and thumb, respectively. Congratulations, you just made a pair of arm warmers/leg warmers that take up zero space, even in a small purse, for less than 5 bucks. ) These will keep you remarkably warmer on a cool summer night, right at that moment when you step out of the bar/restaurant/movie and realize it is not so hot when the wind picks up and the sun is gone, all without lugging a jacket with you :)
• Know your bicycle. You should at least know these things: what your brakes look and feel like when they are working properly; how to change a flat; and how to check that your wheel's axles are indeed locked into your bike's frame. Better to know these things before you set out for work and discover that your brakes weren't connected while coming to a red light, or down a hill. This seriously happens to people all the time. HI-larious for me to watch, terrifying for you to experience. So know how to assess your brakes, lube your chain, put air in your tires and you should be pretty good to go.
• Give yourself enough time. Being in a hurry is the surest way to make dumb and unsafe decisions on the road. See "know your route" above to help you figure out the length of time you'll need to safely get to your destination. Practice your route on a Sunday, when you aren't in a hurry, and you aren't thinking about your 9 am meeting with a client, for instance.
• Don't spend an arm and a leg for gear you may not need. You want gloves and a hat? Try Andy&Bax they have plenty of bike friendly products at wallet friendly prices. (I especially like my Marcella wool gloves for 10 bucks, their selection of "survival" socks, handkerchiefs (I'm no fan of the "farmer-blow" technique), army issue wool sweaters that stay warm even when wet....) Some other faves of mine: Nau, Rei (check out their outlet online), Sanderson Safety Supply has great "bike" sunglasses for a buck and reflective fabrics, etc. Another place that has been invaluable to me is GoodWill: some of my best gear has been second hand.
• Panniers and baskets are great for those of us that have wimpy shoulders and don't like to feel like a sweaty pack mule. Bikefarm and City Bikes sell these at very reasonable prices. These will make you not hate commuting. I promise.