Is this jacket rain resistant?

Yes , jacket is rain resistant.

what is the difference between the iconic racer jacket and the original iconic racer jacket which this is?

I purchased the Original Iconic Racer Jacket. The last one I had was a men's small, so I got a small in this one. It is way, way, way too small for me and I just found out the return policy is only for 30 days. I am not happy and wish I'd never bought it. Let the buyer beware.

I wear a 16 34/35 dress shirt 5’9 175 lbs Avg build. medium or large?

Based on my experience with sleeve length buying a L and XL, in your case I would recommend Large. Reason: I wear a 16.5 - 36 dress shirt, so according to the size chart I took Large. In reality the sleeves felt an inch too short, but were long enough on the next size up.

Is it warm for winter time?

Hi Thanks for your interest. This jacket is a Spring or Fall jacket it is too lightweight for the winter. Thanks DoverDealz

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