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We can say "that dress looks nice on you" or "you look nice in that dress"

But for small objects such as glasses or rings.

It's okay to say "the glasses look nice on you" but it sounds strange to say "you look nice in the glasses".

Is it natural to say "Do the glasses feel comfortable on you" or "Do you feel comfortable in the glasses"?

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    "You look nice in those glasses" is fine. "Do you feel comfortable in them?" also seems OK to me. Dec 17, 2020 at 9:21
  • @KateBunting, is it ok or colloquial to say "you look nice in that ring/ earring" and "Do you feel comfortable in that ring/ earring"?
    – Tom
    Dec 18, 2020 at 0:52
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    Although I said 'in glasses' was fine (and others seem to agree - see here ), spectacles are on the edge of what's acceptable with the expression 'in a garment'. We wouldn't say 'in a ring' or 'in earrings'. Better to use 'wearing that ring' or 'with that ring on'. Dec 18, 2020 at 9:48

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In this case, I think "Do the glasses feel comfortable on you?" is closer to the meaning you have in mind. "Do you feel comfortable in the glasses?" is more likely to refer to the wearer's psychological comfort -- maybe they've never worn glasses before or are trying an unusual style.

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