
Say what you will, a dress is the absolute best bike attire. You don't need to worry about it getting caught in your chain like a pant leg, you are free to move as you please, and--chosen wisely--it will dry almost instantly once you're out of the snow or rain. As previously mentioned, in winter you will be wearing a sturdy base layer (at least on the bottom, maybe also on the top). Paradoxically, a summer-weight dress is a better choice. Here's why: you are not looking to the dress for warmth--your base layer, your coat (more on coats another time), and perhaps a sweater will handle that. You are looking to your dress for looks and for quick-dryability. Three words: POLYESTER, RAYON, SPANDEX. These are good ingredients for a bike-to-work dress. Depending on the skirt style, a dress can run the gamut from a lot to a whole lot of extra fabric. Therefore, you want to make drying time as quick as possible. The lighter and more synthetic the fabric, the quicker it will dry. You can spend a bit more and get some smart-fabric dresses, which are out there if you look for them at fancy female athlete-geared makers like athleta, title nine, and patagonia; but these will honestly offer you very little--if any--advantage over regular dresses in the right fabrics and tend not to be as attractive. As always, avoid cotton at all costs. I will approve of a merino dress for very cold days but it will be too hot for most. I recommend you pick up some cute, cheapish dresses at a place like Marshall's or TJ Maxx or for sale online (on sale) at sites like Bluefly and Piperlime.
You will wear these dresses all year round. In summer, they'll be your whole outfit (more on summer biking in a skirt later), in Fall and Spring they'll go over a pair of tights, and in winter they'll go over your baselayer. You want to be sure to choose darker colors and/or prints. These will not show road dirt, if you occasionally splash yourself, or sweat, if you're running late and really have to gun it. Be sure the fabric is stretchy and the skirt is full enough to allow for full range of motion in the legs. Sometimes, I'll get a shorter length dress and simply roll it up when I get on the bike. This prevents the dress from getting dirty, and modesty is not a problem in the winter because you're wearing a longer coat and heavy-weight leggings. For all of these reasons, you'll be happy you went with POLYESTER - RAYON - SPANDEX because it does not wrinkle and you can throw it in the washing machine as often as you'd like. Silk, by the way, works in some ways but not in others. It dries quickly, but can be very wrinkly. A silk blend will be better in the end than 100%.

