The increasing digitization of contemporary media and culture -- particularly in the West -- is changing how companies market themselves to their target audiences. As the millennial generation increases its online presence and its use of mobile digital technologies, companies whose main consumers lie within this demographic are having to shift their marketing tactics to become more technologically- and mobile-friendly. The world of social media, in particular, has become the second (virtual) home for much of the millennial population. How they dress, where they go, and what they eat are all becoming increasingly impacted by the companies, brands, people, and trends they “follow” online. In this Major Research Project (MRP) I will focus on the ways companies are marketing to millennials by focusing on the ways two clothing brands favoured by millennials are marketing and branding themselves on Instagram. I demonstrate that while these companies’ brand values may be exceedingly different from one another, their social media/Instagram strategies are surprisingly similar. That is, I will argue that these two clothing brands follow a distinctly similar set of social media marketing techniques in order to bring the best shopping experience through the use of images and captions -- into the digital world and to their millennial audiences. In other words, by adhering to a sort of social media orthodoxy, these brands are able to create a stronger connection between themselves and their millennial generation of followers.