diff --git a/src/Fonts/FontRegistry.php b/src/Fonts/FontRegistry.php
index c6c5102..b1055f0 100644
--- a/src/Fonts/FontRegistry.php
+++ b/src/Fonts/FontRegistry.php
@@ -15,7 +15,7 @@ public function addFont(string $filePath): void
         $this->fontFiles[] = $ttfFile;
     }
 
-    public function findMatchingFont(?string $family, bool $italic, float $weight): ?FontFile
+    public function findMatchingFont(?string $family, ?string $style, float $weight): ?FontFile
     {
         if (empty($this->fontFiles)) {
             return null;
@@ -32,9 +32,19 @@ public function findMatchingFont(?string $family, bool $italic, float $weight):
             }
         }
 
-        // Attempt to find the closest-weight match with correct family and italicness.
-        $match = $this->closestMatchBasedOnWeight(function (FontFile $font) use ($family, $anyFontFamily, $italic) {
-            return ($anyFontFamily || $font->getFamily() === $family) && $font->isItalic() === $italic;
+        // Attempt to find the closest-weight match with correct family and cursiveness.
+        $match = $this->closestMatchBasedOnWeight(function (FontFile $font) use ($family, $anyFontFamily, $style) {
+            $result = ($anyFontFamily || $font->getFamily() === $family);
+            $isItalic = $font->isItalic();
+            $isOblique = $font->isOblique();
+            switch ($style) {
+                case 'italic':
+                    return $result && ($isItalic || $isOblique);
+                case 'oblique':
+                    return $result && ($isOblique || $isItalic);
+                default:
+                    return $result && !($isItalic || $isOblique);
+            }
         }, $weight);
 
         // Attempt to match just based on the font family.
diff --git a/src/Fonts/TrueTypeFontFile.php b/src/Fonts/TrueTypeFontFile.php
index 93586a3..e1a91e0 100644
--- a/src/Fonts/TrueTypeFontFile.php
+++ b/src/Fonts/TrueTypeFontFile.php
@@ -44,7 +44,11 @@ public function getFamily(): string
 
     public function getWeight(): float
     {
-        return $this->weightClass ?? ($this->subfamily === 'Bold' || $this->subfamily === 'Bold Italic' ? 700 : 400);
+        return $this->weightClass ?? (
+            $this->subfamily === 'Bold' ||
+            $this->subfamily === 'Bold Italic' ||
+            $this->subfamily === 'Bold Oblique' ? 700 : 400
+        );
     }
 
     public function isItalic(): bool
@@ -52,6 +56,11 @@ public function isItalic(): bool
         return $this->subfamily === 'Italic' || $this->subfamily === 'Bold Italic';
     }
 
+    public function isOblique(): bool
+    {
+        return $this->subfamily === 'Oblique' || $this->subfamily === 'Bold Oblique';
+    }
+
     public function isMonospace(): bool
     {
         // TODO implement detection for monospace fonts
diff --git a/src/Rasterization/Renderers/TextRenderer.php b/src/Rasterization/Renderers/TextRenderer.php
index 886f03b..11e4c21 100644
--- a/src/Rasterization/Renderers/TextRenderer.php
+++ b/src/Rasterization/Renderers/TextRenderer.php
@@ -33,9 +33,8 @@ protected function prepareRenderParams(array $options, Transform $transform, ?Fo
 
         $fontPath = null;
         if (isset($fontRegistry)) {
-            $isItalic = $options['fontStyle'] === 'italic' || $options['fontStyle'] === 'oblique';
             $weight = self::resolveFontWeight($options['fontWeight']);
-            $matchingFont = $fontRegistry->findMatchingFont($options['fontFamily'], $isItalic, $weight);
+            $matchingFont = $fontRegistry->findMatchingFont($options['fontFamily'], $options['fontStyle'], $weight);
             if ($matchingFont !== null) {
                 $fontPath = $matchingFont->getPath();
             }