Hindsight: Re-Thinking an Awkward Conversation

I don't know what made it come to mind, but this has been bugging me for the past week or so:  Some years ago, my male boss asked me to talk to a young female employee about her choice of attire.  Although her attire didn't bother me personally, I knew what he was talking about.  The way she dressed made her come across as very, very young and somewhat professionally naive.  She was wearing nice new suits and nice new buttoned shirts, which were perfectly appropriate -- except that the shirts were just a touch too tight, with the opening just a touch too low.  The clothes were just a touch too form-fitting.  (And come to think of it, the effect was possibly made worse because the shirts were typically in very delicate, feminine colors that were just a little too close to the color of her skin.)

I reluctantly attempted to have the conversation, and it was very awkward.  I could not figure out any way to describe the issues that I knew my boss was concerned about with any degree of delicacy (although I tried).  I knew what I was saying would likely come across as personal criticism, or possibly an unhealthy attitude on my own part, or both.

Looking back on it now, I think I see a way I could have approached the topic - not foolproof, but it might have been marginally better for everyone concerned.  My goal was to open her eyes to an issue that she might want to address, in a way that did not leave her feeling "objectified" or unduly worried that she had made a really bad impression.

The approach I've been thinking about would go something like this:

So-and-so has asked me to speak with you on a topic that may be a little sensitive.  I hope you'll understand that our intentions are good, and take what I say with a grain of salt.  When you're thinking about how to present yourself in a business environment, there's a fine line sometimes between what is professional and what is perceived (whether correctly or not) as alluring.  You're on the right side of the line, I want to make that clear.  But when you're new to the profession, it's sometimes helpful to move another few centimeters back from the line; it reassures everyone around you that you know where the line is.  It's totally unfair, but a shirt that is closely tailored can be interpreted as tight when you're young; and I personally find even at my age that buttoned shirts can be tricky when the placement of buttons makes me choose between "too close for comfort" and "too buttoned up".  Again, I don't think you're on the wrong side of the line; you're clearly not dressed for a club.  And you certainly don't need to be dowdy or shapeless - we're talking a slight ratcheting down or a slight stepping back from the line, rather than a wholesale transformation.  I hope you'll take these comments in the spirit they're intended, which is to help you put your best foot forward while you're cursed with the "problem" of youth and beauty.  It's a good problem to have, and I can actually assure you that it will work in your favor as you establish yourself in the profession.  

It still might have been better to refuse to have the conversation at all (which is what I would probably do now), but a speech along those lines might have at least had a reasonable shot at communicating what my boss hoped to communicate.