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Did she know you wore heels too?

Funny you should mention this. I met one of my superiors in the parking lot, while waiting for other coworkers to arrive. It was cold, I opened the back door to climb in her car and get out of the cold. She apologized for all the heels and a great pair of booties that were laying in the footwell where I climbed in..."That's quite alright..." I said, "great heels indeed"....

I agree (he said, whilst grovelling and fawning at his superior's superbly-booted feet). 🙊

Yes, and there are ways of putting these things honestly without using loaded or derogatory language. Happily all of use here seem to be quite adept and diplomatic at expressing an opinion.

I think that is a good summary of what is often a difficult situation. If someone presents here his latest footwear for 'approval', it is easy to say 'nice' but potentially awkward (or worse) to say, honestly, 'not for me' - let alone 'ugh!'. I sometimes wonder about theatre critics; they can be absolutely scathing about a production or performance but their opinion, good or bad, is expected and generally welcomed, albeit not perhaps by the promoters and actors.

And there are so many of them out there!

I suppose it is wise to consider that silence doesn't necessarily equal tacit approval. The main point I was trying to make is that the internet allows people to be their worst selves, evidently without guilt. This refresher course in human fecal matter has definitely swayed my personal needle toward not making a "How to Walk in High Heels" video. Who needs that kind of abuse?

I take a similar view. If I can’t say something positive I say nothing at all. Everyone’s tastes are different and the fact that we all wear heels, of whatever style, a.ready puts all of us well out of the bell curve. Obviously if a member announces in a post that they’re planning to wear their pink patent thigh high stilettos on their golfing holiday in Dubai one would be doing them no favours by staying silent

So many variables to consider when offering "constructive criticism" indeed. I guess so much depends on your relationship with those receiving the criticism and the place (online/in person/email etc) the criticism will be offered. You are right of course, offering insincere positive comments may not be doing that person any favors. I do my best not to offer "phony compliments", tend to just say little or nothing when I see something that does not look good to me. I remember this stern advice the parents would give when we were kids. And, I must keep in mind, everyone's taste (especially in heels) is different, beauty is in the eye of the beholder.... In the case of guys in heels, one must also consider where a fellow is on his heeling journey. It is hard enough for a guy to muster the courage to go against idiotic societal norms in order to explore fashions he has only secretly admired in the past, I tend to err on the side of encouragement in cases like this.