I’m a first year male teacher looking for input on tactfully handling female student dress code violations. All homeroom teachers at my private school are expected to resolve dress code problems before students are sent to first period. I’ve had two recent incidents where I was cited for failing to enforce dress code standards in my homeroom. Both incidents are similar in that I failed to address female students coming to homeroom, then going to first period, still wearing sweatpants under their uniform skirts. While technically our student handbook forbids students arriving to school with sweatpants under skirts, our principal permits it as long as the sweatpants are removed before homeroom – generally when students first go to their lockers, because our winter climate has been bone chilling. My reluctance to enforce the policy stems primarily from embarrassment, as a male authoritative figure, in having to instruct any high school aged female to “remove her sweatpants” before she can leave my homeroom. But on the other hand, I cannot allow myself to get anymore administrative citations. My inexperience makes me dread having to enforce dress code rules under these circumstances.