The fashion industry is establishing its presence on a number of visual-centric social media like Instagram. This creates an interesting clash as fashion brands that have traditionally practiced highly creative and editorialized image marketing now have to engage with people on the platform that epitomizes impromptu, realtime conversation. What kinds of fashion images do brands and individuals share and what are the types of visual features that attract likes and comments? In this research, we take both quantitative and qualitative approaches to answer these questions. We analyze visual features of fashion posts first via manual tagging and then via training on convolutional neural networks. The classified images were examined across four types of fashion brands: mega couture, small couture, designers, and high street. We find that while product-only images make up the majority of fashion conversation in terms of volume, body snaps and face images that portray fashion items more naturally tend to receive a larger number of likes and comments by the audience. Our findings bring insights into building an automated tool for classifying or generating influential fashion information. We make our novel dataset of 24,752 labeled images on fashion conversations, containing visual and textual cues, available for the research community.