This paper examines advertising images of fashion brands in vertical social network site (SNS) from the viewpoints of message strategies. Vertical social network sites are types of social curation systems applied to social networking, where information is selected, organized, and maintained. Fashion brands communicate with consumers by presenting images on vertical SNSs, anticipating improvements in brand image, popularity, and loyalty. Those images portray content for particular brands and seasonal concepts, thus creating paths for product sales information. Marketing via SNSs corresponds to relationship marketing, which refers to long-term interrelationship and value augmentation between the company and consumer, and viral advertising, which relies on word of mouth distribution via social network platforms. Taylor’s six-segment message strategy wheel, often used for analyzing viral ads, was applied to conduct a content analysis of the images. A total of 2,656 images of fashion brands advertised on Instagram were selected and analyzed. Results indicated that brand values were somewhat related to the number of followers. Follower rankings and comment rankings were also correlated. In general, fashion brands projected sensory messages most often. Acute need and rational messages were less common than other messages. Sports brands and luxury brands presented sensory messages, whereas fast fashion brands projected routine images most often. Fashion brands promoted on vertical SNSs should portray advertising images that combine message strategies.