Instagram is a popular social networking application that allowsusers to express themselves through the uploaded contentand the different filters they can apply. In this study we look atthe relationship between the content of the uploaded Instagrampictures and the personality traits of users. To collect data, weconducted an online survey where we asked participants tofill in a personality questionnaire, and grant us access to theirInstagram account through the Instagram API. We gathered54,962 pictures of 193 Instagram users. Through the GoogleVision API, we analyzed the pictures on their content and clusteredthe returned labels with the k-means clustering approach.With a total of 17 clusters, we analyzed the relationship withusers’ personality traits. Our findings suggest a relationshipbetween personality traits and picture content. This allow fornew ways to extract personality traits from social media trails,and new ways to facilitate personalized systems.