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1.
During WWII prostitutes who followed the troops around, sometimes wore army boots or combat boots. It's akin to calling some one's mother a prostitute.
"your mother wears army boots" is a vintage version og a "your momma" insult.
by geeflyboy February 15, 2011
 
2.
your mom has to work, somewhat specific to army work or working in the army, it is an old saying that probably existed when women were not allowed to do much of anything except sleep with thier husbands and clean thier kitchens in the nude.
ha, your dads so bad at working that your Mother wears army boots to keep your family afloat.
by lyison May 13, 2006