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I know that for prayer (davening), you're supposed to be dressed "appropriately", e.g. not in your pajamas; the rule of thumb I'd heard was "as you normally would when seen in public." (Rabbi Enkin has a post about the "hat and jacket" on Hirhurim.)

What if I'm fully dressed, but I also have on top of that my -- winter coat? Gloves? Ski mask? How important is it that I take those OFF before davening?

I'm assuming being over-formally-dressed -- e.g. tuxedo or coat-and-tails -- is never a problem? (Unless you can't concentrate on your davening because everyone in shul is making faces at you ...)

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I can't answer your "how important" question definitively. I expect that only a posek could. However, my suspicion would be that the standard for what you ought to take off should be the same as the standard for what you ought to put on.

For example, if your standard for putting on is what you'd wear for an audience with a mortal head of state, then you'd probably wear a suit and tie, and you'd certainly not wear any sort of outerwear. If your standard is what you'd wear to work, and that means business casual, then you can probably get away with a light jacket but not a winter coat.

I can't imagine a standard that includes gloves or masks. It seems to me that there's no polite (indoor) situation in which you wouldn't look funny with these on. I'm having trouble thinking of a standard that includes overcoats.

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I would take as part of the premise of the question that the environment where the davening takes place is one that is conducive to wearing winter gear. If while on your ski vacation you realize you should daven mincha alone, out in the cold, must you stri of your coat, gloves etc? Alternatively, if the shul you are in has just had its heater break, such that it is very cold, can you wear your coat? –  Ze'ev Felsen Jun 24 '11 at 16:12
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How would you dress if you were meeting the president of the US? The prime minister of Israel? L'havdil, what if you were meeting with one of the gedolei ha-dor? Perhaps your answer to these questions should be your guide to answering your question.

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Jay, Welcome to mi.yodeya, and thanks very much for posting this answer! Please consider registering your account by clicking on "register," above. This will give you access to all of mi.yodeya's features and will let you take full credit for your contributions. –  Isaac Moses Mar 11 '10 at 14:48
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The standard you suggest is frequently cited and makes sense, considering Whom you present yourself before in davening. However, it seems to me that almost no one practices it. How many people do you see routinely putting on a suit and tie for davening (not counting people who dress thus regularly for work)? –  Isaac Moses Mar 11 '10 at 15:01
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I have also heard this guideline mentioned often, and really never see it followed in practice. Would any "normal" person shuckle and shake before a head-of-state? Is there any room to argue that we do not need to be concerned about outward appearances before Hashem, Who can see through the physical and directly into the spiritual? –  Jeremy Mar 16 '10 at 14:21
    
I too have heard this guideline, but have difficulty with it on the practical level. Where I work, I could actually meet the president of the US and if that were to happen, I would wear my best suit. But I daven every day, three times a day, and there is no way I could on the practical level wear my best suit everytime I daven. Most of the time when I daven I am dressed "casual". –  Dennis Aug 8 '13 at 19:12
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