I have a similar problem. I have a Micargi Tahiti NX3 beach cruiser. I pull an equally cheap 'Master Cycle' kids trailer behind it. I have been starting to plan a 'classic' looking trailer build for after my 15 month old daughter out grows the trailer. I know, I know, it's going to be a while. I wanted to throw out the rainbow stuff and find a cool container to put on it. I've decided for the container I'm going to use a grocery cart and line it with diamond plate and make a hinged flush top for it out of the same. I figured if I paint it matte black it should look pretty good behind my cruiser. Then I realized I will need to disassemble the wheels and paint the rims red to match my bike. Then I realized that it won't have sweet ducktail fenders like my bike does. So now I'm thinking of doing a ground up build.

I want to use the grocery cart so I can detach it and push it right into the store. I think I'm going to look for some replacement parts for my bike and see if I can source just the front wheel and fender then get two of them. Maybe a third mounted up somewhere as a spare. I've been wanting to learn to tig weld for a while. So, I think I will come up with a frame design and build it out of aluminum.

Has anyone seen a classic or cruiser looking full fendered enclosed trailer. If I didn't want a cart that was pushable I would build a tear drop motorcycle style trailer. Like you see going down the road behind a fully dressed touring motorcycle.