There is a bond between the turtleneck pullover and the chukka boots. Both items appear raw in a refined almost elegant way. Both are integrating opposite styles.
The turtleneck, a.k.a the roll neck, is versatile. The man of action likes it, and the thinker likes it. Aviators, racing drivers, skiers and fishermen need the turtleneck for a practical purpose, that is, protecting the neck. They have also become exponents of a turtleneck action style. The intellectual, the man of vita contemplativa, needs the roll neck for opposing himself to the businessman with shirt and tie. The intellectual has made the turtleneck a symbol of wit and critical thinking.
In other words, the turtleneck is a carrier of history. It is not pure style. It is social action as well.
Chukka boots are less burdened by history. They have a dim equestrian connection to the polo sport by its name “chukka”, which means a period or a span of time in polo. Apart from that I can’t imagine a strong social dependency. Like the turtleneck chukka boots fall in the category of small casual. They are for a sport coat, a turtleneck and jeans or moleskin trousers, not for a suit.
The famous dessert boots, which are a less sophisticated version of chukka boots defined by a thick blake-stiched crepe rubber sole instead of a welted sole, are for knit and odd trousers mainly. They can look too soft and casual to be used with a sport coat.