Grape and cotton are agricultural products with high pesticide usage. With an eye towards sustainability, regions are looking towards organic farming to protect soil health. However, given the higher prices associated with organic products, it is crucial to understand consumer attitudes and perception towards such products in order to shift consumer behaviour. To this end, we conducted two sets of studies focusing on organic cotton (in the form of stuffed toys) and wine (Chianti DOCG). For both products, two studies were carried out using (unbeknownst to the participants) identical samples. In Study 1, participants were told which of the two products was “organic” and which was “conventional”. Liking, willingness to pay (WTP), and evaluation of product properties (textural or flavour pleasantness for cotton and wine, respectively) were then collected. In Study 2, participants were only told which product was organic only after they had made their initial preference decision. They then evaluated product properties and WTP. For stuffed toys, all consumers (N = 59) were willing to pay more for the organic toy, even though only consumers with high tendency to buy organic products found it more pleasant to touch. Furthermore, consumers (N = 33) were willing to pay more for the organic toy regardless of their original preference. For wine, consumers (N = 128) were also willing to pay more for the “organic” wine, but only if they had high tendency to buy organic products. Moreover, consumers (N = 57) were only willing to pay more for organic wine if they had preferred it initially. Overall, this work highlights that consumers are willing to pay more for organic products; however, this stems from concern for environmental sustainability in the case of cotton, but from taste preference in the case of wine. Moreover, organic labelling led to a more positive perceptual evaluation of cotton toys, while this halo effect did not carry over to wine.