The dialogue between slow and fast fashion has gained great prominence in recent years particularly in terms of sustainability. In the forward value chain, fast fashion companies are most often considered to be unsustainable whereas the slow fashion brands are comparatively more planet-friendly. However, the discussionon the trade-off between sustainability and “speed of fashion” (classified into slow and fast fashions) in the post-retail segment is still limited. A deeper understanding, however, would not only contribute towards conceptualizing the post-retail initiatives, but would also shed light on how these are differentially undertaken by various types of fashion businesses in terms of generating sustainable value. This study proposes sustainable value generation in terms of closing the material and responsibility loops. It further reveals that the trade-off in post-retail is not as rigid as itis in the forward value chain. However, fast fashion offers the lowest potential todisplace the purchase of new clothes to close the material loop whereas the redesign brands offer the highest; moreover fast fashion is less liable to take extended responsibilities compared to the slow fashion brands. It can be concluded that fast fashion is somewhat “stuck in the middle” in comparison to the slow and redesign brands in terms of generating value through closing the loop activities.