Can an algorithm create original and compelling fashion designs to serve as an inspirational assistant? To help answer this question, we design and investigate different image generation models associated with different loss functions to boost creativity in fashion generation. The dimensions of our explorations include: (i) different Generative Adversarial Networks architectures that start from noise vectors to generate fashion items, (ii) a new loss function that encourages creativity, and (iii) a generation process following the key elements of fashion design (disentangling shape and texture makers). A key challenge of this study is the evaluation of generated designs and the retrieval of best ones, hence we put together an evaluation protocol associating automatic metrics and human experiment studies that we hope will help ease future research. We show that our proposed creativity loss yields better overall appreciation than the one employed in Creative Adversarial Networks. In the end, about 61% of our images are thought to be created by human designers rather than by a computer while also being considered original.