One book which was focused on the evolution of Kuwait's political culture is Jill Crystal's Oil and Politics in the Gulf: Rulers and Merchants in Kuwait and Qatar. (I should note that I read the first edition, published in 1990.) Crystal did a good job explaining how the merchants, whom today we might better call businessmen, were bought out of politics in exchange for economic opportunity. I admit, however, that looking at the matter as a historian I found her overall presentation unsatisfactory. Crystal is a political scientist, and I'm pretty sure this began life as her dissertation. It feels like a stereotypical political science dissertation in that she takes two similar countries and tries to account for their political differences. She concludes that the key factor was that Kuwait had a strong merchant class when Qatar didn't. The democratic tradition arose in part because this merchant class developed a sense of group identity and wanted to continue to participate in state decision-making, leading ultimately to the 1938 Majlis movement usually cited as Kuwait's democratic beginning.
As I said, I find this unsatisfying. The presence of merchants doesn't automatically lead to the formation of a democratic tradition. One is left, not so much why the merchants developed a sense of corporate identity, which I can see evolving out of the Kuwaiti taxation system, but why their political activity took the form it did. I haven't looked at the primary sources, and have doubts as to whether the British records we usually rely on for these events would really address the issue, but I suspect a better explanation lies in the same reason Kuwait had all these merchants, and that is geography. Kuwaitis had a lot of ties to Iraq, and during the 1930's many of the merchants behind the Majlis movement were Arab nationalists who wanted the country to become part of Iraq. Iraq had a parliament, and I suspect that is the model the merchants were following. Frankly, I also think Kuwait's rulers also over-reached more, prompting a series of reactions.
Mary Ann Tetrault's Stories of Democracy highlighted another relevant aspect of Kuwaiti history, and that is the Iraqi invasion of 1990 as transforming Kuwaitis sense of nationhood and political action. I know when I was there back in December, it seemed like it had become a key event in the consolidation of a Kuwaiti identity; it was good to have this perception of a mere two days confirmed by an actual Kuwait expert, who adds critical nuance about the difference between those who remained in the country during the Iraqi occupation and those who were outside. Her account of the interplay between the invasion and the democratization movement is fascinating and difficult to summarize, but in describing the effect, she was at pains to point out that the sense of popular organization carried over into the post-invasion politics, as did a new self-confidence. She reported many people as saying: "We aren't afraid of the Sabah. We survived Saddam Hussein."