By the way, the boots don't say "Maine Hunting Shoe" on the back of the lower part of the boot then they are not true Maine Hunting Shoes, they are the PC version where the name was eliminated so as not to offend those who oppose hunting.
Interesting footwear. Not sure I'm sold on the aesthetic, but it would be tremendously practical in some of the heavy rain we get here, especially as I don't care for wellies.
If in doubt - overdress.
They were designed for function, not fashion, and they preform fairly well under modest conditions. I have worn mine for almost 40-years but the older I get the less I rely on them. Very little ankle support, virtually no arch support and the famous chain-link tread can be downright dangerous climbing over "snotty" logs and on steep climbs in wet grass. That being said, they were ideal when I spent a week early last summer in northern Maine. It rained every day, we were in/out of Grand Lakers multiple times each day and we followed moose trails between ponds carrying packs. They kept my feet dry and kept me upright on the slippery rocks in the trails. Guess that's why they are called Maine Hunting Boots.
I also have a pair of their camp shoes and I all but live in them October - May. Easy on/off, warm comfortable and they keep my feet dry. They are much more practical for walking around civilized areas.