The phrase “Are you wearing that for a bet?” is often used humorously or in a teasing manner to question someone’s choice of clothing or appearance, implying that the style or outfit is so outlandish or unusual that it seems like it might have been chosen as part of a dare or a bet. It’s not a question that would typically be asked in a serious context. It’s a light-hearted way to express surprise or disbelief at someone’s fashion choice.