Unfortunately, our system currently does not allow for buyers to bundle two items from the same listing, even if they are different sizes. Poshmark's inventory has historically been concentrated in single-item listings (since we've been predominantly a peer-to-peer resale marketplace), so have never needed this multi-unit bundle capability. Buyers will need to buy in separate transactions if they want to purchase multiples of a single listing. We have this on the product roadmap, but do not yet have a completion date.
