tsl

I guess it all depends on what you're dressing in.

My winter gear goes on pretty quickly.

Assume as a summertime baseline: socks, shorts, jersey, shoes, cycling skullcap and gloves. (Helmet too.)

In winter I replace the jersey with a baselayer, add windproof, water-resistant, insulated bib tights over my shorts, and a second top layer--usually a long-sleeve t-shirt. My Lake winter cycling boots go on even faster than my three-season shoes. Jacket takes no time at all, and a winter skullcap or balaclava takes no more time than the summer-weight article they replace.

Gloves do take more time. I double-glove using a summer-weight long-finger cycling glove inside a pair of Cannondale Windfront gloves. I manage most of the time to get all the different Velcros (two pairs of gloves, the jacket sleeves, and my RoadID) stuck to one another. Takes a bit to get them sorted out after that. That's the only step that takes me significantly longer than in summer.

This gets me down to the lower teens (F). In the single-digits, I add knee-warmers under the tights, wear both a winter-weight cycling skullcap and a balaclava, and switch to lobster gloves, which go on faster than the double-gloves I wear in the "warmer" cold weather.

Above freezing to about 50F, I switch to non-insulated wind-front bib tights and delete the inner glove layer, and forgo the second top layer if I wear the jacket, or add arm-warmers under the two long-sleeve layers if I don't.

Edit: BTW, are you just starting now, or did you start in the autumn? If you're starting now, you'll no doubt need more layers than if you started by acclimating to the cold in the autumn. So there's another way to dress faster--ride straight through and allow you body to get acclimated to the cold so you need fewer layers.