Twitter was an integral part of Donald Trump’s communication platform during his 2016 campaign. Although its topical content has been examined by researchers and the media, we know relatively little about the style of the language used on the account or how this style changed over time. In this study, we present the first detailed description of stylistic variation on the Trump Twitter account based on a multivariate analysis of grammatical co-occurrence patterns in tweets posted between 2009 and 2018. We identify four general patterns of stylistic variation, which we interpret as representing the degree of conversational, campaigning, engaged, and advisory discourse. We then track how the use of these four styles changed over time, focusing on the period around the campaign, showing that the style of tweets shifts systematically depending on the communicative goals of Trump and his team. Based on these results, we propose a series of hypotheses about how the Trump campaign used social media during the 2016 elections.