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So I've killed off some well equipped Imperials, looted their bodies and want to equip their armor. Does the game take into consideration that I look like an Imperial when I interact with pro-Imperial or anti-Imperial characters going forward?

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No one in the game refuses to speak to you based on what you're wearing.

They'll even talk to you if you're freezing your rear off, stark-naked, in front of them. (Though as Communist Duck points out, they do remark on it.)

Edit

I have found that the Captain of the Guards in Solitude gets offended if you walk around in Stormcloak armor. Instead of making generic "captain of the guard" comments, if you're wearing the Stormcloak armor, he'll accuse you of being a Stormcloak supporter. If you say to his face, in the Imperial Army's Headquarters, that you hate the Empire, he'll get understandably angry and attack you (though he accepts yields, so clearly he doesn't want to kill you that much...).

So in short, your outfit might add additional dialog options, but as far as I've been able to determine, it never precludes you from any.

This is different from New Vegas, where it did work like that, but remember, that game wasn't made by Bethesda.

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    If you're not wearing anything, people will actually comment on it. – The Communist Duck Nov 15 '11 at 17:19
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    @sXe I've updated my answer to have more info. Generally, I think that's right. – Raven Dreamer Nov 15 '11 at 23:28
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    I initially thought it was like Fallout:New Vegas, so I stored Stormcloak and Imperial armor in my inventory and changed armor depending on who I am dealing with. Thanks to this, I will now wear my Dark Brotherhood armor everwhere. Muahahahaha!! – galacticninja Nov 16 '11 at 1:04
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    But does wearing the wrong factions armour or no armour effect your effective speechcraft? i.e. does my chance to persuade or intimidate change, or can I sell items for as much in no/different armour? – Canageek Jan 14 '12 at 22:55
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    @Arkive The sneaky and hands to yourself comments are due to your high sneak skill. You get similar comments about your abilities if you have high magic skills (usually people fearful of your magic) or combat skills – Doc Mar 28 '14 at 14:39

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