If I recall, from the late great foggymountain, back in the fifties and before, Dunhills were some of the better pipes but by no means the most expensive. For a long time, Kaywoodie cost more, and both were within reach of the working guy. Or gal. That's a classic. Foggy' remembered working in pipe shops in Manhattan in the 1950's, where presumably he sold his share of both brands.
I hear this repeated a lot, but I honestly don't think that is true. At least in the 40-50-60's.
In the 1941 George Yale catalog, Barling's and Dunhill pipes were $10 minimum and the highest priced Kaywoodie's in the catalog were the same (drinkless pipes were 3.50 and supergrains were 5.00). In other words, the buy in for the cheapest Dunhill and Barling's pipe was the same as the most expensive Kaywoodie. This holds true for the 1945 catalog from the same company, except base for Dunhill is now $15 and the highest priced Kaywoodie is now at $12.
The 1949 and 1955 RTDA catalogs show increasing price splits. Again the only Kaywoodie pipes that even remotely approached Dunhill in price were the ultra rare lines such as the 95er and the centennials.
By the early 60's it was game over with the Owl Shop asking more than $28 for a small smooth Dunhill and $15 for a high grade Kaywoodie connoisseur.
This isn't a slag on Kaywoodie, they made some really excellent pipes, but by trying to make a pipe for everyone, they lost the majority of the high end market from an early point in time.
Bob