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You can start selling right away. Just make sure you don't get too invested financially because there is the possibility your mark gets rejected. You will not have the full benefit of your federal registration until your application is officially approved, but once you start using your mark in commerce you will gain common law trademark which helps to prove usage and ownership. In fact, usage in commerce is part of the application process. At some point, you will get a Notice of Allowance and you will have 6 months to submit proof of use.
 

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Yes, actually selling shirts is what proves usage. But since the sale itself is not tangible, you will eventually need to submit something commonly associated with commerce (image of your product, image of a hangtag, a screenshot of your website, digital file of marketing materials, etc).
 

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You would need to register your business with your state and get any necessary licenses or permits. A tax id number is good too, this way you can get wholesale prices and not pay tax when you buy supplies, blank shirts, etc. If you register as a sole proprietor, you can use your SSN instead of getting a tax id number, but not everyone feels comfortable with that.
 
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