Noob needs clothing help

[VeloVT]

If you are in a mild climate, arm warmers and a light wind vest are excellent investments. Everyone has a different thermostat , but I can get by with a light jersey, arm warmers (which may get rolled down if I'm working hard) and a vest down to maybe 50 degrees. I also think knickers are a great purchase. There is a real temperature range (for me at least) in which shorts are too cold and tights are too hot. For me, that runs from about 40-60.

In in-between weather (low/mid 40s-low 50s), instead of a long sleeve jersey (which are often quite warm, even if they are not thick and fleecy), I will often wear a longsleeve silkweight long underwear top underneath a short sleeve jersey, kind of like BSG does. Sometimes I'll throw arm warmers on over the baselayer.

Jerseys... I like them because I like the slim fit and the pockets. Obviously, you can find other athletic tops with a slim fit, but I find I really do use the pockets -- for tools, for cell phone and wallet and lipbalm (which I need to put on frequently while riding), and sometimes for snacks.

Jackets... you don't want an insulated jacket unless it's under 40 degrees -- in fact, probably not much over 35. Otherwise you'll sweat and get cold. You also don't want to wear a waterproof jacket in warm weather unless it's raining and you have to, for the same reason. Light wind jackets make a big difference.

You can definitely buy strategically and get a few versatile pieces that serve you well instead of buying an entire wardrobe.