I started with steel, rode about 3 miles round-trip, and did in plain clothes/shoes, carried a backpack, worst weather was warm rain.

Switched to a better fitting steel roadie, started experimenting with handlebar setups and more expensive tires, added a rack a paniers, still plain clothes.

Now I'm aluminum/carbon, have my setup dialed in, ride as often as I possibly can, carry a backpack, ride in/with traffic up to 40mph, and now wear form-fitting cycling gear. The worst weather I ride in now is...well I only don't ride when there is lightning. I've settled into a riding style that focuses on higher cadence as cycling is, for now, the only activity I do to maintain my fitness.