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Let's say I wanted to sell t-shirts/hoodies with Supreme box logo (font, color & shape), but custom text inside. Would it be legal?

Normally, I would assume it wouldn't. However, I know that the design is originally a creation of Barbara Kruger, not Supreme, so I wonder whether they are able to claim ownership over their brand logo or not.

In my search for an answer, I found a few articles regarding Supreme trademark problems, but I don't know how reliable they are and how does it affect my issue:

I have even come across an online shop selling exactly this kind of stuff and they just disallow the word "Supreme" in the box. Is that all it takes to make this kind of business legal?

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    This seems to be a fairly generic question about what the law is, not a request for specific advice. – David Siegel Apr 1 at 9:13
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From those articles, it seems that at least some versions of the "Supreme" Logo have been successfully registered. Therefore, any "confusingly similar" logo would be infringement, and could subject anyone using such logos in trade to an infringement suit. And it seems that the owners of the Supreme line are quite willing to sue.

It does not, therefore, follow that every possible logo consisting of a red box with white lettering in the Futura font would be an infringement. Similarity depends on the overall effect of a mark, and the main test is the likelihood of confusion or deception of reasonable customers or potential customers. If the text is, say, multiple words, none of which is the word "supreme" or any similar word, then it might arguably be not the Supreme logo, but a different logo that has some similar elements. (If you describe it as "the Supreme logo but" you make your opponent's case for them.)

Whether a specific choice of words would be confusingly similar is more specific than this forum can get. You should consult a trademark lawyer for advice on that point. But if in doubt you might want to go with a greater difference. How about a blue box instead of a red one?

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