There's No Place Like My Trademark

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Dear Rich: We have a t-shirt business in which we use a slogan and then add a geographic location -- imagine something like, "I Wish I Were in [City]" or "There's No Place Like [City]." I know our slogan is ornamental and I want to overcome that objection. I have read and talked to other attorney friends that if we can add a logo/artwork to the shirt itself (think "Life is Good" pre-artwork incorporated, and then post artwork incorporated), we would then be able to protect the slogan (in addition to the logo/artwork under copyright law). 

If your goal is to cordon off a few words such as "I Wish I Were in ..." or "There's No Place Like ..." and stop others from using those words in connection with the names of geographic locations, you've got a very difficult challenge ahead of you.
What about Life is Good? The Life is Good trademark strategy (which we wrote about recently) is a combination of scale, legal maneuvering, and aggressiveness. Keep in mind that even though Life is Good merchandise generates $100 million annually and the company has spent a small fortune on trademark registrations and enforcement, other companies have been able to register the mark for other goods and services. And it's not clear -- at least there's no legal precedent -- that the company can stop others from using other "Life is ...." combinations although they've threatened to halt Life is Nutz, Life Sucks, Life is Gay, and even went after LG Electronics' use of Life's Good (the companies settled). In summary, unless you're well-funded, famous, and willing to take an aggressive hardline view of your rights, you'll have a difficult time protecting segments of your slogan.
What is an ornamental objection? The issue of "ornamentality" typically arises when seeking to register a trademark for t-shirts or other clothing and the claimed mark is the featured element of the clothing. The trademark examiner is essentially saying that buyers are not associating the art or logo with a particular source. For example, the buyer of a There's No Place Like Modesto t-shirt does not associate that shirt with a particular source or company. However, the same is not true for the buyer of a Just Do It t-shirt. If you're facing an ornamentality refusal, the USPTO suggests five ways to overcome it.
Creating a slogan and drawing used in conjunction with the shirts. What if you sought to register the words There's No Place Like ... in conjunction with an image? Is that a method of obtaining protection for a phrase that might be otherwise unregistrable? No, not likely. Even if you register the phrase with a design (commonly referred to as a “design plus words mark”), "the strength and value of that protection may be limited." As for the copyrightability of a "design plus words mark," that depends on the degree of originality, creativity and in some cases, ornateness of the artwork (something that even the Life is Gooders had to grapple with). Of course, copyright won't be an issue if all that is copied is the slogan and not the artwork.