Purpose - This paper seeks to investigate shopping orientation and online clothing purchases across four different gender-related purchasing contexts. A conceptual model for understanding the impact of shopping orientation on consumer online clothing purchase is proposed and tested both in a general setting and across purchasing contexts.Design methodology approach - Questionnaires were distributed to 1,150 Danish household addresses by use of the "drop-off-call-back" survey method. A total of 441 households returned usable responses from either one or both adults in the household. Most adults provided responses with respect to purchasing clothing for themselves and for their partner, making a total of 906 cases distributed across the four purchasing contexts. T-tests and linear structural equation modelling were utilised to investigate expectations and hypotheses.Findings - The results support the expected differences in men's and women's shopping orientations and willingness to purchase clothing online. On average, consumers indicate that reduced difficulty in selecting items is sorely needed when purchasing clothing online. However, when evaluated across different purchasing situations, perceived difficulty in selecting items is an important action barrier only for women. Less fun significantly affected online clothing purchases for men purchasing clothing for themselves, but not for women doing the same.Research limitations implications - Future research may seek to verify the proposed conceptual model using a range of specific clothing items across different purchasing situations. Future research may also expand the model by suggesting other influencing factors on consumers' online clothing purchasing.Practical implications - In order to attract more men, online clothing retailers should improve perceived online fun, whereas difficulty in selecting items should be reduced in order to attract more women.Originality value - The study is unique in the sense that it investigates online clothing behaviour across four different gender-related purchasing contexts.