A reader writes:

I have a question about a point that is now, thankfully, moot.

My previous manager, Rufus, wasn’t an especially ethical individual and failed to fulfill many of his expected duties. He was also kind of a creep. We all just put up with his unsavory and unprofessional comments, and occasionally pushed back when we felt it was important to do so.

One situation, though, left me without clear direction. I am non-binary, though I wasn’t out at work (a few coworkers pieced it together, but it wasn’t widely known). When I began to discreetly wear a binder to work, Rufus began to make comments about how I needed to look more professional. Over time, this evolved into getting feedback on my wardrobe as often as a few times per week.

It wasn’t a one-time fluke. It was a regular part of my life for months. I tried wearing an acceptable outfit (chinos and crewneck sweater) with my binder, then again with an underwire bra. With the underwire, I was complimented on dressing professionally. With the binder or a sports bra, I was again criticized. All the while, I was actually dressing above our company standards, which were snappy casual. I stopped wearing jeans and switched to business casual (chinos, khakis, and slacks, always with a structured top and nice shoes). My binder wasn’t visible, nor did it cause visible cleavage. It didn’t matter. One person I worked with closely and who knew my gender identity actually brought my boss’s comments up to me, so I wasn’t just being sensitive.

While I don’t hold Rufus in high regard for a number of reasons, I will be fair and say I don’t think he did this on purpose. I think he just preferred the way I looked some days and didn’t bother to question what, specifically, he liked. It was kind of like when a manager asks a femme if she’s feeling okay when she forgoes makeup. Except it wasn’t makeup, it was my body, and a part of my body about which I am dysmorphic.

I never said anything. I did not feel safe outing myself to him. Instead, I asked him to elaborate what was or wasn’t professional about specific outfits. He wasn’t able to give me anything, but he also didn’t stop the comments until he abruptly quit. He just laughed when I mentioned the frequency of his comments.

Was there anything else I could have done in this situation, other than out myself to him or upper management?

P.S. This story has a happy ending. I am now under a wonderful manager who gives prompt and actionable feedback about my job and only my job. I am learning lots of interesting new skills, and I no longer dread going to work. I have had no contact with Rufus.

Rufus is an ass.

He was indeed harassing you around gender presentation — and around the appearance of your boobs, specifically — whether he was consciously aware of it or not.

And really, when a manager finds themselves giving someone repeated dress code feedback, they have a high obligation to interrogate themselves about exactly where you’re violating expectations and then provide clear and specific guidance on that. “You need to look more professional” doesn’t meet that bar. And “you don’t look sufficiently professional even though you’re in the same outfit I judged professional last week” really should have raised some flags in his mind about what his judgments were based on.

Also, I’m guessing you wouldn’t have gotten this feedback if you were just naturally flatter-chested and appeared that way every day, so either (a) in the most generous reading, he was unconsciously responding to “her figure looks less pleasing to me today” and not bothering to think about why before trying to make that your problem, or (b) he was aware of why and still felt free to make that your problem, which would make it full-on sexual harassment and would make him a terrible person. Either way: a jerk, and just a question of degrees.

If you had a time machine, it would be interesting to go back and say to him, “This is the same outfit I wore last week that you told me looked professional. Every time you’ve given me this feedback, I’ve been in nice pants, a structured top, and nice shoes. I of course want to follow our dress code, so can you please give me more specific feedback about exactly where I”m violating it?” Or simply, “Can you tell me what specifically is out of compliance, so that I can ensure I’m within the dress code going forward?”

It sounds like you did ask him to elaborate and if your framing was similar to this and still elicited no details, then ideally your next step would be HR. HR isn’t useful for every type of problem you might encounter with a boss, but for something like this — where (a) you’re being told you’re violating a company policy and you don’t think you are and/or (b) gender presentation is involved, they’re often much better trained to handle it than a random manager might be. Not always, of course — there’s bad HR out there — but if you’d gone to see HR in person on one of the days Rufus told you that you were dressed unprofessionally, relayed his feedback, explained that he was telling you this regularly, and asked for guidance, there’s a decent chance they’d have talked to Rufus and shut it down (even without you needing to out yourself).

I’m sorry you had to work for such a jackwagon and I’m glad you’re in a better job now.