It is not my goal to give a complete company history on this website, there is enough information you can find on both the Hunter website and on Wikipedia. Two things do stand out; first the Hunter Original Wellington Tall was introduced in 1956 and was hardly popular around that time. Hunter stuck with their design and continued production for the same rain boots for over 60 years though. These boots hold a piece of heritage that continuous today.
Second, Hunter boots attracted mostly the richer upper class country folks due to their relatively high prices. The choice for Hunter was mostly motivated by the durability of the boots which could easily last 20 years or more. Prime example of the richer upper class wearing Hunter boots is Princess Diana with a pair of green hunter boots in her engagement photos:
This engagement picture was taken before Princess Diana got a complete “fashion make-over” and out of respect for her I will not discuss her wardrobe or fashion style based on a picture that old as it would not do justice to her as a person.
Over the years the brand had healthy, but low, growth numbers and the boots stayed functional, traditional, and mostly for the richer people to wear upcountry. Advertisements were directed at country folks with ads in the printed magazine “Shooting Times”, and the urban population barely knew the brand or was interested in buying rubber rain boots: