Research on tax behaviour or attitudes towards tax evasion has rarely taken into account the political preferences of taxpayers. The present research aimed to explore the relationship between political ideology and attitudes toward tax compliance within the “slippery slope framework” (Kirchler, Hoelzl, & Wahl, 2008). We conducted a quantitative survey (N = 272) and two online focus groups with self-employed taxpayers in Italy, and found significant differences between left-leaning and right-leaning taxpayers. These two groups were characterized by two different pathways that lead to greater tax compliance, and attached different meanings and values to tax behaviours. In particular, left-leaning taxpayers expressed higher levels of voluntary cooperation and showed reactance to the coercive power of authorities, whereas right-leaning taxpayers expressed higher levels of enforced tax compliance and were more averse to tax evasion with increased trust in authorities and institutions. Although further research on this topic is advisable, these results bear relevant theoretical and practical implications.