diff --git a/web/src/core/mantle/evaluator/simple/index.test.ts b/web/src/core/mantle/evaluator/simple/index.test.ts
index 101cb4a9a..e1ee8094b 100644
--- a/web/src/core/mantle/evaluator/simple/index.test.ts
+++ b/web/src/core/mantle/evaluator/simple/index.test.ts
@@ -485,4 +485,51 @@ describe("Conditional styling", () => {
       },
     });
   });
+
+  test("Nested styling at 2nd degree", () => {
+    expect(
+      evalLayerAppearances(
+        {
+          marker: {
+            pointColor: "#FF0000",
+            pointSize: {
+              expression: {
+                conditions: [
+                  ["Number('0.32423%') < 1", "200"],
+                  ["true", "1"],
+                ],
+              },
+            },
+            labelTypography: {
+              fontSize: 20,
+              color: {
+                expression: {
+                  conditions: [
+                    ["${blah}==='value'", "color('#ff0000')"],
+                    ["true", "color('#ffffff')"],
+                  ],
+                },
+              },
+            },
+          },
+        },
+        {
+          id: "x",
+          type: "simple",
+          properties: {
+            blah: "value",
+          },
+        },
+      ),
+    ).toEqual({
+      marker: {
+        pointColor: "#FF0000", // blue
+        pointSize: 200,
+        labelTypography: {
+          fontSize: 20,
+          color: "#FF0000",
+        },
+      },
+    });
+  });
 });
diff --git a/web/src/core/mantle/evaluator/simple/index.ts b/web/src/core/mantle/evaluator/simple/index.ts
index 5552129f2..657256fd1 100644
--- a/web/src/core/mantle/evaluator/simple/index.ts
+++ b/web/src/core/mantle/evaluator/simple/index.ts
@@ -59,15 +59,22 @@ export function evalLayerAppearances(
       properties: layer.properties || {},
     };
   }
+
+  return Object.fromEntries(
+    Object.entries(appearance).map(([k, v]) => [k, recursiveValEval(v, layer, feature)]),
+  );
+}
+
+function recursiveValEval(obj: any, layer: LayerSimple, feature?: Feature): any {
   return Object.fromEntries(
-    Object.entries(appearance).map(([k, v]) => [
-      k,
-      Object.fromEntries(
-        Object.entries(v).map(([k, v]) => {
-          return [k, evalExpression(v, layer, feature)];
-        }),
-      ),
-    ]),
+    Object.entries(obj).map(([k, v]) => {
+      // if v is an object itself and not a null, recurse deeper
+      if (hasNonExpressionObject(v)) {
+        return [k, recursiveValEval(v, layer, feature)];
+      }
+      // if v is not an object, apply the evalExpression function
+      return [k, evalExpression(v, layer, feature)];
+    }),
   );
 }
 
@@ -76,23 +83,30 @@ export function clearAllExpressionCaches(
   feature: Feature | undefined,
 ) {
   const appearances: Partial<LayerAppearanceTypes> = pick(layer, appearanceKeys);
-
   Object.entries(appearances).forEach(([, v]) => {
-    Object.entries(v).forEach(([, expressionContainer]) => {
-      if (hasExpression(expressionContainer)) {
-        const styleExpression = expressionContainer.expression;
-        if (typeof styleExpression === "object" && styleExpression.conditions) {
-          styleExpression.conditions.forEach(([expression1, expression2]) => {
-            clearExpressionCaches(expression1, feature, layer?.defines);
-            clearExpressionCaches(expression2, feature, layer?.defines);
-          });
-        } else if (typeof styleExpression === "boolean" || typeof styleExpression === "number") {
-          clearExpressionCaches(String(styleExpression), feature, layer?.defines);
-        } else if (typeof styleExpression === "string") {
-          clearExpressionCaches(styleExpression, feature, layer?.defines);
-        }
+    recursiveClear(v, layer, feature);
+  });
+}
+
+function recursiveClear(obj: any, layer: LayerSimple | undefined, feature: Feature | undefined) {
+  Object.entries(obj).forEach(([, v]) => {
+    // if v is an object itself and not a null, recurse deeper
+    if (hasNonExpressionObject(v)) {
+      recursiveClear(v, layer, feature);
+    } else if (hasExpression(v)) {
+      // if v is not an object, apply the clearExpressionCaches function
+      const styleExpression = v.expression;
+      if (typeof styleExpression === "object" && styleExpression.conditions) {
+        styleExpression.conditions.forEach(([expression1, expression2]) => {
+          clearExpressionCaches(expression1, feature, layer?.defines);
+          clearExpressionCaches(expression2, feature, layer?.defines);
+        });
+      } else if (typeof styleExpression === "boolean" || typeof styleExpression === "number") {
+        clearExpressionCaches(String(styleExpression), feature, layer?.defines);
+      } else if (typeof styleExpression === "string") {
+        clearExpressionCaches(styleExpression, feature, layer?.defines);
       }
-    });
+    }
   });
 }
 
@@ -100,6 +114,10 @@ function hasExpression(e: any): e is ExpressionContainer {
   return typeof e === "object" && e && "expression" in e;
 }
 
+function hasNonExpressionObject(v: any): boolean {
+  return typeof v === "object" && v && !("expression" in v);
+}
+
 function evalExpression(
   expressionContainer: any,
   layer: LayerSimple,
diff --git a/web/src/core/mantle/types/appearance.ts b/web/src/core/mantle/types/appearance.ts
index 1dfafb951..1824860aa 100644
--- a/web/src/core/mantle/types/appearance.ts
+++ b/web/src/core/mantle/types/appearance.ts
@@ -10,7 +10,7 @@ import type {
 } from "./value";
 
 export type LayerAppearance<T> = {
-  [K in keyof T]?: T[K] | ExpressionContainer;
+  [K in keyof T]?: T[K] | LayerAppearance<T[K]> | ExpressionContainer;
 };
 
 export type LayerAppearanceTypes = {