In this essay I will study three different paintings by the Swedish artists Lars Lerin and Gösta Adrian Nilsson (also known as GAN). All of these pieces incorporate sailors as part of their motives. The aim of the study is to analyse how these pieces differ in how they convey homoerotic themes. Both of these artists refer to their sexuality through their artistry, the sailor being a common motive between the two. I will also examine how the sailor relate to different ideas of masculinity. To do this I will use methods from both the iconologic and semiotic schools of art analysis, before comparing the different pieces, presenting my interpretations of them. The result of this study shows that these artists use varying methods to present their sexual identity. The motives of GAN are more subtle than those of Lars Lerin, relying on symbolic interpration rather than men posing suggestivily. This is not suprising, as homosexuality was still illegal during GANs life. The artists also portray masculinity in different ways.