diff --git a/modules/juce_graphics/native/juce_mac_Fonts.mm b/modules/juce_graphics/native/juce_mac_Fonts.mm
index 216ad69b87..7f72a8e2fd 100644
--- a/modules/juce_graphics/native/juce_mac_Fonts.mm
+++ b/modules/juce_graphics/native/juce_mac_Fonts.mm
@@ -33,11 +33,22 @@
 
 namespace CoreTextTypeLayout
 {
+    static String findBestAvailableStyle (const String& typefaceName, const String& style)
+    {
+        const StringArray availableStyles (Font::findAllTypefaceStyles (typefaceName));
+
+        if (! availableStyles.contains (style))
+            return availableStyles[0];
+
+        return style;
+    }
+
     static CTFontRef createCTFont (const Font& font, const float fontSize,
                                    const bool applyScaleFactor)
     {
         CFStringRef cfFontFamily = font.getTypefaceName().toCFString();
-        CFStringRef cfFontStyle = font.getTypefaceStyle().toCFString();
+        CFStringRef cfFontStyle = findBestAvailableStyle (font.getTypefaceName(),
+                                                          font.getTypefaceStyle()).toCFString();
         CFStringRef keys[] = { kCTFontFamilyNameAttribute, kCTFontStyleNameAttribute };
         CFTypeRef values[] = { cfFontFamily, cfFontStyle };
 
@@ -1070,7 +1081,6 @@ StringArray Font::findAllTypefaceStyles (const String& family)
         NSArray* style = [styles objectAtIndex: i];
         results.add (nsStringToJuce ((NSString*) [style objectAtIndex: 1]));
        #endif
-
     }
 
     return results;
diff --git a/modules/juce_graphics/native/juce_win32_DirectWriteTypeface.cpp b/modules/juce_graphics/native/juce_win32_DirectWriteTypeface.cpp
index 81ee555a6d..4cd18af3a1 100644
--- a/modules/juce_graphics/native/juce_win32_DirectWriteTypeface.cpp
+++ b/modules/juce_graphics/native/juce_win32_DirectWriteTypeface.cpp
@@ -148,14 +148,14 @@ public:
         uint32 fontFacesCount = 0;
         fontFacesCount = dwFontFamily->GetFontCount();
 
-        for (uint32 i = 0; i < fontFacesCount; ++i)
+        for (int i = fontFacesCount; --i >= 0;)
         {
             hr = dwFontFamily->GetFont (i, dwFont.resetAndGetPointerAddress());
 
             ComSmartPtr<IDWriteLocalizedStrings> faceNames;
             hr = dwFont->GetFaceNames (faceNames.resetAndGetPointerAddress());
 
-            if (font.getTypefaceStyle() == getLocalisedName (faceNames))
+            if (i == 0 || font.getTypefaceStyle() == getLocalisedName (faceNames))
                 break;
         }