I think it's very weird and slightly distasteful for a man to comment on a woman's style of dress. I give the odd compliment when I think it's welcome and pretend to have an opinion when my girlfriend asks me which dress she should wear, that's it.
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Are you saying that if she bought a hideous dress that didn't suit her you'd lie to her? That's not helpful at all. Women would rather be told if we looked like crap.
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Said someone who’s never been married to a woman. Trust me, it isn’t worth it.
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Stock answer: You look nice. Saying "fine" is death.
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That kind of shaming tends to come from women, at least in my life. My office manager dislikes leggings + tunic or sweater-dress styles, and considers them inappropriate. She figures you're basically showing up to work without pants.
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She has asked me outright on one occasion, of a sweater tunic/dress (bum fully covered down to mid-thigh), "So do you consider this a dress?" The implication was clearly that it was whorish.
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I've never had a man comment on my clothing save for my dad who objected to my using Julia Roberts Pretty Woman character as a style model when I was a teen, but I think he made the right call.
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Mum is the only one who bitches about my clothes. (Complains that I don’t wear dresses&skirts) Somehow she hasn’t figured out that they’re horribly impractical when you commute by motorbike, even though she’s been Dads pillion ballast for longer than I can remember

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I can’t say I’ve ever told a woman how to dress. I dread when my wife is getting ready for something and asks how she looks in one of numerous outfits she has tried on
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"Doctor" Martens - who's cuter than Helen Pluckrose?
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Does 'does this make my bum look big?' count?
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I often get comments on my style from both genders, stating that is hipster or feminine. However, I don’t choose clothes to please other people. So it does not bother me.
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