diff --git a/toolkit/themes/winstripe/global/jar.mn b/toolkit/themes/winstripe/global/jar.mn
index 6bab309b94f3..561e93c6ecd0 100644
--- a/toolkit/themes/winstripe/global/jar.mn
+++ b/toolkit/themes/winstripe/global/jar.mn
@@ -150,8 +150,10 @@ classic.jar:
         skin/classic/global/toolbar/Lighten.png                  (toolbar/Lighten.png)
         skin/classic/global/toolbar/spring.png                   (toolbar/spring.png)
         skin/classic/global/tree/columnpicker.gif                (tree/columnpicker.gif)
-        skin/classic/global/tree/sort-asc.gif                    (tree/sort-asc.gif)
-        skin/classic/global/tree/sort-dsc.gif                    (tree/sort-dsc.gif)
+        skin/classic/global/tree/sort-asc.png                    (tree/sort-asc.png)
+        skin/classic/global/tree/sort-dsc.png                    (tree/sort-dsc.png)
+        skin/classic/global/tree/sort-asc-classic.png            (tree/sort-asc-classic.png)
+        skin/classic/global/tree/sort-dsc-classic.png            (tree/sort-dsc-classic.png)
         skin/classic/global/tree/twisty-clsd.png                 (tree/twisty-clsd.png)
         skin/classic/global/tree/twisty-open.png                 (tree/twisty-open.png)
 
@@ -305,8 +307,10 @@ classic.jar:
         skin/classic/aero/global/toolbar/Lighten.png                     (toolbar/Lighten.png)
         skin/classic/aero/global/toolbar/spring.png                      (toolbar/spring-aero.png)
         skin/classic/aero/global/tree/columnpicker.gif                   (tree/columnpicker.gif)
-        skin/classic/aero/global/tree/sort-asc.gif                       (tree/sort-asc.gif)
-        skin/classic/aero/global/tree/sort-dsc.gif                       (tree/sort-dsc.gif)
+        skin/classic/aero/global/tree/sort-asc.png                       (tree/sort-asc-aero.png)
+        skin/classic/aero/global/tree/sort-dsc.png                       (tree/sort-dsc-aero.png)
+        skin/classic/aero/global/tree/sort-asc-classic.png               (tree/sort-asc-classic.png)
+        skin/classic/aero/global/tree/sort-dsc-classic.png               (tree/sort-dsc-classic.png)
         skin/classic/aero/global/tree/twisty-clsd.png                    (tree/twisty-clsd-aero.png)
         skin/classic/aero/global/tree/twisty-clsd-rtl.png                (tree/twisty-clsd-rtl-aero.png)
         skin/classic/aero/global/tree/twisty-clsd-hover.png              (tree/twisty-clsd-hover-aero.png)
diff --git a/toolkit/themes/winstripe/global/listbox.css b/toolkit/themes/winstripe/global/listbox.css
index 3f93163d1cc7..84000fdeb81d 100644
--- a/toolkit/themes/winstripe/global/listbox.css
+++ b/toolkit/themes/winstripe/global/listbox.css
@@ -130,11 +130,19 @@ listheader[sortable="true"]:hover:active {
 }
 
 .listheader-sortdirection[sortDirection="ascending"] {
-  list-style-image: url("chrome://global/skin/tree/sort-asc.gif");
+  list-style-image: url("chrome://global/skin/tree/sort-asc.png");
+}
+
+.listheader-sortdirection[sortDirection="ascending"]:-moz-system-metric(windows-classic) {
+  list-style-image: url("chrome://global/skin/tree/sort-asc-classic.png");
 }
 
 .listheader-sortdirection[sortDirection="descending"] {
-  list-style-image: url("chrome://global/skin/tree/sort-dsc.gif");
+  list-style-image: url("chrome://global/skin/tree/sort-dsc.png");
+}
+
+.listheader-sortdirection[sortDirection="descending"]:-moz-system-metric(windows-classic) {
+  list-style-image: url("chrome://global/skin/tree/sort-dsc-classic.png");
 }
 
 /* ::::: listcell ::::: */
diff --git a/toolkit/themes/winstripe/global/tree.css b/toolkit/themes/winstripe/global/tree.css
index 04a7445e9872..46db5e61e947 100644
--- a/toolkit/themes/winstripe/global/tree.css
+++ b/toolkit/themes/winstripe/global/tree.css
@@ -319,11 +319,19 @@ treechildren::-moz-tree-column(insertafter) {
 }
 
 treecol:not([hideheader="true"]) > .treecol-sortdirection[sortDirection="ascending"] {
-  list-style-image: url("chrome://global/skin/tree/sort-asc.gif");
+  list-style-image: url("chrome://global/skin/tree/sort-asc.png");
+}
+
+treecol:not([hideheader="true"]) > .treecol-sortdirection[sortDirection="ascending"]:-moz-system-metric(windows-classic) {
+  list-style-image: url("chrome://global/skin/tree/sort-asc-classic.png");
 }
 
 treecol:not([hideheader="true"]) > .treecol-sortdirection[sortDirection="descending"] {
-  list-style-image: url("chrome://global/skin/tree/sort-dsc.gif");
+  list-style-image: url("chrome://global/skin/tree/sort-dsc.png");
+}
+
+treecol:not([hideheader="true"]) > .treecol-sortdirection[sortDirection="descending"]:-moz-system-metric(windows-classic) {
+  list-style-image: url("chrome://global/skin/tree/sort-dsc-classic.png");
 }
 
 /* ::::: column picker :::::  */
diff --git a/toolkit/themes/winstripe/global/tree/sort-asc-aero.png b/toolkit/themes/winstripe/global/tree/sort-asc-aero.png
new file mode 100644
index 000000000000..d5bb668e7e52
Binary files /dev/null and b/toolkit/themes/winstripe/global/tree/sort-asc-aero.png differ
diff --git a/toolkit/themes/winstripe/global/tree/sort-asc-classic.png b/toolkit/themes/winstripe/global/tree/sort-asc-classic.png
new file mode 100644
index 000000000000..b2f04ec12ff7
Binary files /dev/null and b/toolkit/themes/winstripe/global/tree/sort-asc-classic.png differ
diff --git a/toolkit/themes/winstripe/global/tree/sort-asc.gif b/toolkit/themes/winstripe/global/tree/sort-asc.gif
deleted file mode 100644
index fa957ac1e759..000000000000
Binary files a/toolkit/themes/winstripe/global/tree/sort-asc.gif and /dev/null differ
diff --git a/toolkit/themes/winstripe/global/tree/sort-asc.png b/toolkit/themes/winstripe/global/tree/sort-asc.png
new file mode 100644
index 000000000000..9c4a82587c4d
Binary files /dev/null and b/toolkit/themes/winstripe/global/tree/sort-asc.png differ
diff --git a/toolkit/themes/winstripe/global/tree/sort-dsc-aero.png b/toolkit/themes/winstripe/global/tree/sort-dsc-aero.png
new file mode 100644
index 000000000000..4e335c55ccc8
Binary files /dev/null and b/toolkit/themes/winstripe/global/tree/sort-dsc-aero.png differ
diff --git a/toolkit/themes/winstripe/global/tree/sort-dsc-classic.png b/toolkit/themes/winstripe/global/tree/sort-dsc-classic.png
new file mode 100644
index 000000000000..60892b95599b
Binary files /dev/null and b/toolkit/themes/winstripe/global/tree/sort-dsc-classic.png differ
diff --git a/toolkit/themes/winstripe/global/tree/sort-dsc.gif b/toolkit/themes/winstripe/global/tree/sort-dsc.gif
deleted file mode 100644
index 5e13c7398f16..000000000000
Binary files a/toolkit/themes/winstripe/global/tree/sort-dsc.gif and /dev/null differ
diff --git a/toolkit/themes/winstripe/global/tree/sort-dsc.png b/toolkit/themes/winstripe/global/tree/sort-dsc.png
new file mode 100644
index 000000000000..64d077a8f4bb
Binary files /dev/null and b/toolkit/themes/winstripe/global/tree/sort-dsc.png differ