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In general, one should not wear clothing inside-out, as per Shulchan Aruch, OC 2:3:

ידקדק בחלוקו ללובשו כדרכו שלא יהפוך הפנימי לחוץ

One should be particular with his cloak to wear it properly, that the inside not be flipped outside.

As the Magen Avraham explains (§3):

ויראו התפירות המגונות

And they will see the disgusting stitches

May one wear his clothing inside-out on Purim, as (a part of) his costume, where the whole point is that one should not be dressed as he normally is?

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    As Poskim abrogate (or, excuse) the issue of Lo Yilbash per Purim costumes, this would presumably be the same; especially since it’s not a halachah (in the legal sense of the word).
    – Oliver
    Commented Mar 21, 2019 at 19:29
  • @Oliver Which is Deorayso! So it is clearly Kal Va Chomer.
    – Al Berko
    Commented Mar 21, 2019 at 19:30
  • @Oliver What about according to those who don’t excuse Lo Yilbash for Purim? While most rely on the Rema’s leniency, not everyone agrees.
    – DonielF
    Commented Mar 21, 2019 at 19:33
  • @DonielF According to those you can also argue that only when one of the things that are kasheh le’shikcha are routinely done (e.g. “ha’ragil b’zeisim”) it’d be a concern, not when it’s done for a joke. OTOH sticklers for ‘dvarim ha’kashim le’shikcha’ (R’ C. Kanievsky et al) might be sensitive even when done on Purim. But, being that actual laws are somewhat mitigated in the spirit of simchas Purim there’s ample room to be less sensitive to something of this nature.
    – Oliver
    Commented Mar 21, 2019 at 19:47
  • 3
    It might help you forget the difference between ארור המן and ברוך מרדכי
    – Heshy
    Commented Mar 21, 2019 at 19:53

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