diff --git a/code/modules/clothing/clothing_ch.dm b/code/modules/clothing/clothing_ch.dm
index 1e97b6d43e..bc3655e87b 100644
--- a/code/modules/clothing/clothing_ch.dm
+++ b/code/modules/clothing/clothing_ch.dm
@@ -1,6 +1,7 @@
 //CHOMP Overrides for if holder is digitigrade
 /obj/item/clothing
-	var/update_icon_define_orig = null
+	var/update_icon_define_orig = null // temp storage for original update_icon_define (if it exists)
+	var/fit_for_digi = FALSE // flag for if clothing has already been reskinned to digitigrade
 
 /obj/item/clothing/proc/handle_digitigrade(var/mob/user)
 	if(ishuman(user))
@@ -20,13 +21,14 @@
 				update_icon_define_digi = "icons/inventory/uniform/mob_digi_ch.dmi"
 			else
 				return
-
-			// only override icon if a corresponding digitigrade replacement icon_state exists
-			// otherwise, keep the old non-digi icon
-			if(icon_state && icon_states(update_icon_define_digi).Find(icon_state))
-
-				// Don't reset if already set
-				if(update_icon_define <> update_icon_define_digi)
+			
+			// Don't reset if already set
+			if(!fit_for_digi)
+				fit_for_digi = TRUE // set flag even if no icon_state exists, so we don't repeat checks
+				
+				// only override icon if a corresponding digitigrade replacement icon_state exists
+				// otherwise, keep the old non-digi icon
+				if(icon_state && icon_states(update_icon_define_digi).Find(icon_state))
 
 					//if update_icon_define is already set to something, place it in a var to hold it temporarily
 					if(update_icon_define)
@@ -36,16 +38,18 @@
 					update_icon_define = update_icon_define_digi
 
 
-		// if not-digitigrade and update_icon_define set by previous digi-user, replacing an 'original' value
-		else if(update_icon_define_orig)
-			update_icon_define = update_icon_define_orig
-			update_icon_define_orig = null
-
-
-		else if(update_icon_define)
-			// if not-digitigrade and update_icon_define set by previous digi-user, but nothing replaced
-			update_icon_define = null
-
+		// if not-digitigrade, only act if the clothing was previously fit for a digitigrade char
+		else 
+			if(fit_for_digi)
+				fit_for_digi = FALSE
+				
+				//either reset update_icon_define to it's old value
+				// or reset update_icon_define to null
+				if(update_icon_define_orig) 
+					update_icon_define = update_icon_define_orig
+					update_icon_define_orig = null
+				else 
+					update_icon_define = null
 
 /obj/item/clothing/shoes/equipped(var/mob/user, var/slot)
 	. = ..()