In this article I explore the idea of ‘signature style’ in celebrity media culture, and outline its relationship to competing demands of recognisability, reinvention, individuality and typicality that inform the celebrity image. I take ‘retro’ as an example, an aesthetic which I understand as broadly and flexibly referencing Western mid-century fashions. My case studies are singer and actress Andra Day and burlesque performer Dita Von Teese, and I examine interviews, profiles, and red carpet coverage to explore how retro style relates to their celebrity image. In my analysis, I focus on how retro style, as a highly visible form of constructed femininity, is interpreted as both tired and tiring. Commentators describe their weariness at the repetitive styles of stars seen as ‘stuck in a rut’, which both emphasises the demand for fashionable celebrity reinvention and downplays the journalistic imperative for novel information that signature style potentially undermines. Day and Von Teese’s looks are also interpreted as exhausting, and the final part of this article examines the relationship between retro as a signature style and aesthetic labour. While celebrity femininity demands high levels of aesthetic labour, the discussion of retro as uniquely wearisome speaks to the politics of ‘natural’ femininity.