This meme might be considered funny or clever because it plays on the double meaning of the word 'tripping'. In the literal sense, it refers to someone stumbling or falling while walking, potentially because of their shoes being laced incorrectly. In the slang sense, 'tripping' can refer to experiencing the effects of hallucinogenic drugs, which is humorously implied by the mention of the shoes being bought from a drug dealer. The added element of using characters from 'Star Trek: The Next Generation' who appear to be reacting to the pun adds to the comedic effect.