Hey T, welcome to the forums. This is really a very broad topic, so it's hard to cover it all at once. For more detailed info, you can search the forums as this topic has been covered many times. But for now, I'll mention a few key points (and keep in mind, these points are specifically related to use on t-shirts).
Originality:
If you are looking to create your own original designs featuring your own original phrases, images and artwork, then you have nothing to worry about. It's completely legal. But if you are creating designs or using elements that are not originally your own (whether it is intentional or not), then you could be infringing on existing intellectual property. Doing so can get you sued by the existing IP owner.
Copyright:
Works of art such as books, poems, songs, screenplays, designs, paintings, photographs, etc, are eligible for copyright. While copyrights can be registered with the US Copyright Office, ownership actually exists as soon as the work is in fixed form. So basically, if a work of art exists, it's copyrighted. Unauthorized usage of copyright is considered IP infringement.
Public Domain:
The exception to the "if it exists, it's copyrighted" rule are works that are in the public domain. Anything prior to 1923 is considered public domain, as is anything that the copyright owner released into the public domain. If you do a Google search for "public domain images" you should find some resources. These images are free to use for any purpose, including commercial use.
Trademark:
Brand names, logos, etc, are eligible to be trademarked. Federal trademarks are registered with the US Patent & Trademark Office. However, trademark ownership can exist without registration. If a mark is being used in commerce, then there is common law trademark. Unauthorized usage of a trademark is considered IP infringement.
Right of Publicity:
All people, famous or not, are granted the exclusive right to profit off their own name and likeness. So any usage of a person's name and likeness without license or permission is considered infringement.
Licensing:
Popular brands like Disney, NFL, Marvel Comics, etc, license their IP for big time money. The official licensed merchandise industry is huge. So infringing on this type of IP is also violating licensing agreements and the chances of being sued goes up dramatically.
Parody:
Creating a parody or spoof of existing IP does not mean you can't or won't be sued. The existing IP owner absolutely has the right to sue for infringement. You can defend yourself in court on the basis of parody or fair use, but it will be up to the judge to decide who wins.
Hope this helps and good luck with making your t-shirts.
Originality:
If you are looking to create your own original designs featuring your own original phrases, images and artwork, then you have nothing to worry about. It's completely legal. But if you are creating designs or using elements that are not originally your own (whether it is intentional or not), then you could be infringing on existing intellectual property. Doing so can get you sued by the existing IP owner.
Copyright:
Works of art such as books, poems, songs, screenplays, designs, paintings, photographs, etc, are eligible for copyright. While copyrights can be registered with the US Copyright Office, ownership actually exists as soon as the work is in fixed form. So basically, if a work of art exists, it's copyrighted. Unauthorized usage of copyright is considered IP infringement.
Public Domain:
The exception to the "if it exists, it's copyrighted" rule are works that are in the public domain. Anything prior to 1923 is considered public domain, as is anything that the copyright owner released into the public domain. If you do a Google search for "public domain images" you should find some resources. These images are free to use for any purpose, including commercial use.
Trademark:
Brand names, logos, etc, are eligible to be trademarked. Federal trademarks are registered with the US Patent & Trademark Office. However, trademark ownership can exist without registration. If a mark is being used in commerce, then there is common law trademark. Unauthorized usage of a trademark is considered IP infringement.
Right of Publicity:
All people, famous or not, are granted the exclusive right to profit off their own name and likeness. So any usage of a person's name and likeness without license or permission is considered infringement.
Licensing:
Popular brands like Disney, NFL, Marvel Comics, etc, license their IP for big time money. The official licensed merchandise industry is huge. So infringing on this type of IP is also violating licensing agreements and the chances of being sued goes up dramatically.
Parody:
Creating a parody or spoof of existing IP does not mean you can't or won't be sued. The existing IP owner absolutely has the right to sue for infringement. You can defend yourself in court on the basis of parody or fair use, but it will be up to the judge to decide who wins.
Hope this helps and good luck with making your t-shirts.