Although flats do help quite a bit in winter riding so you can get you're foot on the ground as quick as possible when you need to, I do personally use my clipless unless it is really icy... but you better be good at uncliping quickly, trust me. Yes, the layer thing can be tricky and does take a bit of trial and error. Here's what I wear to least point you in the right direction. For upper body I start with long sleeve athletic shirt. It's the same kind of stuff that Under Armor makes, but mine is Reebok and much cheaper (bought them at Kohl's). You don't want the thick winter kind though, that's more for skiing and other winter sports not heavy on cardio. The material wicks away moisture wonderfully what is exactly what you want so if you do sweat a little you won't freeze. I top that with a jersey which once again wicks moisture well and provides another layer. Next depends on the temp. 40's I where a thin wind breaker jacket with vents in the pit area. 30's I where a little bit thicker wind breaker but still not too thick. Even colder weather I wear a fleece vest with the thicker wind breaker. Don't use a thick winter coat, you'll overheat. On the bottom if it's 40's I wear a wind breaker pants. 30's I wear cotton long underwear with shorts over them. Even colder and I put the wind breaker pants over the long underwear. For gloves I wear Pearl Izumi gloves that are made with a thin material so you can handler your bike easily, but are still really warm. If it's really cold I wear thicker gloves over them. For feet I wear wool dress socks with biking socks over them plus I have Pearl Izumi winter shoe covers. If you don't want to fork over the money for shoe covers wearing a plastic bag between the dress socks and biking socks does wonders. Just remember that if you're warm in what you are wearing when you start that you are over dressed. You should be cold. I know it's hard motivating yourself to go out in the cold to ride, but try it your first time in a group ride. It's a blast. I hope this helps.