Imo, Linden Lab pushed Second Life to soon when they got real life companies to join second life in around 2007. There were only normal prims back then, not even sculpts so everything looks bad like the American Apperal clothes were just basic system layers and cost L$300 for a basic system layer hoodie. Of course it wouldn't work because it doesn't look good and no one wants to buy them. But these days however there might be a chance since we have mesh with normal and spec maps now and things look better.
If Second Life tries to get companies into SL again they should get Converse and Doc Martens to make legit mesh boots and sneakers with their brands on it because people would actually buys these and there are already "knockoff" or "inspired by" versions of Doc Martens boot and Converse sneakers being made and sold by creators in SL and they do sell.
Who knows maybe there will be a second wave when second life goes mainstream again and it actually catches on.