In my 50 some odd years in the United States, I've never hear that term used as an idiomatic expression. I found a song, "How To Actually Wear Pants," which seems to sarcastically deal with some one who can't even put their pants on to start the day. I think that fits the sense of your expression.

Put your right leg in the right pantleg
Put your left leg in the left pantleg
Pull up the zipper (zzzzzip!)
And push the button through the hole
Give it a rub for good luck
Comb the tassels to eliminate knots
(We don't want to get tangled)
Roll up the cuffs
Three rolls
Or knee high
Whichever comes first
Inflate the personal space maintenance buffers
And tune the jingle bells
To F sharp
Myxilydian
Insert a package of gum into one of the back pockets
But not both
Now you are wearing your pants
Now you are wearing your pants
Now you are wearing your pants
Now you are wearing your pants






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Note added at 1 hr (2009-11-24 14:52:33 GMT)
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"push the button through the hole," seems always to be used in the context of clothing. Mostly it is used in the literal sense of the child or disabled person having difficulty with that seemingly simple task.
Are you asking about that expression, or you looking for a similar expression which is indeed idiomatic?