For my wife and I, never anything less than boots, jeans, and leather vests. Usually fingerless gloves too. If we're not just tooling around town, or if we get on the highway at all, the jackets and helmets come out, no matter how hot it is out there. Dew-rag and shades top things off to keep off the sun.
In chilly weather, the leather pants and chaps see more action. Lined flannel shirts plus the vest, or regular flannel under my jacket. Thicker socks in the boots and full coverage gloves.
For winter riding, I wear... well, everything
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Thermal underwear, leather pants, chaps. Lined gloves with oversized fingerless gloves worn over them. Face mask. Helmet and helmet liner. Thermal shirt, flannel shirt, vest, leather trench coat. Gotta wear layers in the winter so you can peel down once you stop - sweating is bad!
And to answer the question, "what do you look like while riding".....
Like this:
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mystic_1