diff --git a/masque/shapes/path.py b/masque/shapes/path.py
index 654cfaa..ad6da5d 100644
--- a/masque/shapes/path.py
+++ b/masque/shapes/path.py
@@ -24,7 +24,16 @@ class PathCap(Enum):
 #                     #     defined by path.cap_extensions
 
     def __lt__(self, other: Any) -> bool:
-        return self.value == other.value
+        if self.__class__ is not other.__class__:
+            return self.__class__.__name__ < other.__class__.__name__
+        # Order: Flush, Square, Round, SquareCustom, Circle
+        order = {
+            PathCap.Flush: 0,
+            PathCap.Square: 1,
+            PathCap.Circle: 2,
+            PathCap.SquareCustom: 3,
+        }
+        return order[self] < order[other]
 
 
 @functools.total_ordering