If the woods are thick on the deer trail with lots of overhanging branches or weeds, etc that will touch your clothes on the way in, then I would suggest, as others, to make a separate entrance trail. One of the most successful bowhunters I know is absolutely meticulous about his entry trails.
On the other hand, if the woods the deer trail is on is sparse such that walking down it leaves no/little chance of contact with vegetation, I would wear rubber boots sprayed down well with scentshield or other spray and not worry too much.
Net, my experience is that the deer I see usually aren't smelling me on the ground where the bottoms of my rubber boots touched...it's on the brush/weeds where my clothes have touched...even if I spray my clothes.
I also think that how much work you want to go through may be proportional to what "kind" of deer you are happy with. If you are solely after big mature whitetails, then you can never be cautious enough. If your goal is to "fill the freezer" then you can probably get by with less caution and still be "successful."