I do a lot of plot hunting where I can watch deer a long time. In my experience, any deer downwind of you can easily smell you 200 yds away if not much, much further. Now, how they react to smelling you depends on the deer. I've had young deer smell me and then continue on as if I wasn't there, some will wait for a second confirmation, but an old doe will get upset, maybe try to locate me by walking in my direction, and maybe stomp her hooves. In all cases, she will promptly leave the area after these antics usually with her tail waving goodbye.
My dog holds an AKC tracking dog title. I spent lots and lots of hours training him to track and what I learned is that my dog would wind scent me if he could. You could see this by him casting downwind of where I walked sometimes 10-20+ yards from my actual path with his nose in the air. As the wind blown scent dissolves (about 1/2 to 1 hr), I would watch him track closer to my actual path with his nose to the ground. How far he cast downwind of my path was based on the age of the track and other conditions such as temperature, whether he was mouth breathing, humidity, and other environmental factors. He was a terrier breed not known for their noses, but he rarely had trouble following a 2 hour trail. What I wore in regard to rubber vs. leather, or clothing made no difference to him whatsoever.
I'm sure deer noses are just as good as my dog's nose and my dog's nose can't be fooled by cover scents or even the scent of another person's cross scent. Finally, my dog can smell me a long, long way off so I know a deer can too. My recommendation is always hunt the wind first.