This is Kyle. Kyle rides his bike to work every day.
I have spent an unreasonable amount of time fussing over exactly what commuter clothes and accessories I need to be a bike commuter.
Kyle: not so much. He did get a decent bike rack and bags so he could carry his suit to work with him rather than wearing it on the way. That arranged, he just started riding his bike to work. Every work-day. Rain or shine (or snow). This approach seems to work really well.
He speaks to people he happens to pass on the way (if they're not behind car glass). He feels good. Commuting on a bike makes him happy -- note the smile on his face. He didn't have to wait till he'd driven home to play in the snow.