Keeping things peachy with your girlfriend. There are three elements required for a successful long-term relationship with your girlfriend: (1) personal hygiene -- we can't stress how important this is, whether it's individual cleanliness, bathroom orderliness, or sanitary kitchen habits, (2) social deportment -- here we're talking about that sense of respect that comes from good table manners, interpersonal restraint and general cordiality, even in the face of overwhelming despair and doom, and (3) lots of laughs - without lots of yuks (hopefully not derived from the misfortune of others), most relationships are doomed. Okay, so that should establish a long term union for your business. Now about your trademark.
Creating a trademark does not create trademark rights. It's true that you will need permission from the artist to use copyrightable artwork in a trademark but you won't need permission to use the name (as that is not copyrightable). Even so, creating the artwork doesn't create trademark rights. Those rights are earned by your use of the mark in commerce. If you're operating as a business--we assume you're a partnership--it would make the most sense to create a partnership agreement and for the partnership to own the marks. Your partnership agreement should address what happens to these assets if the partnership breaks up or if one partner wants to buy out the other. Nolo, our employer (insert FTC disclaimer here) has books that can help you do that.
Your bankruptcy plan. We're not clear about your plan to retain ownership of the trademark to avoid bankruptcy. Your fashion business (or whoever owned the marks) would have to license the marks to the business. So, wouldn't the license become part of the bankruptcy plan? The Dear Rich Staff are not experts on that stuff but we wouldn't count on your approach. (And anyway if the company went into the bankruptcy, doesn't that mean that the brand has failed? So what would be the value of the mark?) Anyway, let's think positive even though we know that's usually not a good idea.