diff --git a/NEWS.md b/NEWS.md
index 66e261da3..2da0cf764 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -5,6 +5,7 @@ Unreleased
 * Introduce `suspenders:inline_svg` generator
 * Introduce `suspenders:factories` generator
 * Introduce `suspenders:advisories` generator
+* Introduce `suspenders:styles` generator
 
 20230113.0 (January, 13, 2023)
 
diff --git a/README.md b/README.md
index 8dbab30f7..dc0d21d78 100644
--- a/README.md
+++ b/README.md
@@ -72,6 +72,22 @@ improvement for the viewer.
 
   [inline_svg]: https://github.com/jamesmartin/inline_svg
 
+### Styles
+
+Configures applications to use [PostCSS][] or [Tailwind][] via
+[cssbundling-rails][]. Defaults to PostCSS with [modern-normalize][], with the
+option to override via `--css=tailwind`.
+
+Also creates a directory structure to store additional stylesheets if using
+PostCSS.
+
+`bin/rails g suspenders:styles --css[postcss:tailwind]`
+
+  [PostCSS]: https://postcss.org
+  [Tailwind]: https://tailwindcss.com
+  [cssbundling-rails]: https://github.com/rails/cssbundling-rails
+  [modern-normalize]: https://github.com/sindresorhus/modern-normalize
+
 ## Contributing
 
 See the [CONTRIBUTING] document.
diff --git a/lib/generators/suspenders/styles_generator.rb b/lib/generators/suspenders/styles_generator.rb
new file mode 100644
index 000000000..512049810
--- /dev/null
+++ b/lib/generators/suspenders/styles_generator.rb
@@ -0,0 +1,60 @@
+module Suspenders
+  module Generators
+    class StylesGenerator < Rails::Generators::Base
+      include Suspenders::Generators::APIAppUnsupported
+
+      CSS_OPTIONS = %w[tailwind postcss].freeze
+
+      class_option :css, enum: CSS_OPTIONS, default: "postcss"
+      desc <<~TEXT
+        Configures applications to use PostCSS or Tailwind via cssbundling-rails.
+        Defaults to PostCSS with modern-normalize, with the option to override via
+        --css=tailwind.
+
+        Also creates a directory structure to store additional stylesheets if using
+        PostCSS.
+      TEXT
+
+      def add_cssbundling_rails_gem
+        gem "cssbundling-rails"
+
+        Bundler.with_unbundled_env { run "bundle install" }
+        run "bin/rails css:install:#{css}"
+      end
+
+      def build_directory_structure
+        return if is_tailwind?
+
+        create_file "app/assets/stylesheets/base.css"
+        create_file "app/assets/stylesheets/components.css"
+        create_file "app/assets/stylesheets/utilities.css"
+      end
+
+      # Modify if https://github.com/rails/cssbundling-rails/pull/139 is merged
+      def configure_application_stylesheet
+        return if is_tailwind?
+
+        run "yarn add modern-normalize"
+
+        append_to_file "app/assets/stylesheets/application.postcss.css" do
+          <<~TEXT
+            @import "modern-normalize";
+            @import "base.css";
+            @import "components.css";
+            @import "utilities.css";
+          TEXT
+        end
+      end
+
+      private
+
+      def css
+        @css ||= options["css"]
+      end
+
+      def is_tailwind?
+        css == "tailwind"
+      end
+    end
+  end
+end
diff --git a/test/generators/suspenders/accessibility_generator_test.rb b/test/generators/suspenders/accessibility_generator_test.rb
index 6728b6c75..c8ca95ef1 100644
--- a/test/generators/suspenders/accessibility_generator_test.rb
+++ b/test/generators/suspenders/accessibility_generator_test.rb
@@ -25,11 +25,7 @@ class AccessibilityGeneratorTest < Rails::Generators::TestCase
       end
 
       test "does not raise if API configuration is commented out" do
-        within_api_only_app do
-          path = app_root("config/application.rb")
-          content = File.binread(path).gsub!("config.api_only = true", "# config.api_only = true")
-          File.binwrite(path, content)
-
+        within_api_only_app commented_out: true do
           run_generator
 
           assert_file app_root("Gemfile") do |file|
diff --git a/test/generators/suspenders/inline_svg_generator_test.rb b/test/generators/suspenders/inline_svg_generator_test.rb
index 141dfea1b..3ed0d3b15 100644
--- a/test/generators/suspenders/inline_svg_generator_test.rb
+++ b/test/generators/suspenders/inline_svg_generator_test.rb
@@ -24,11 +24,7 @@ class InlinveSvgGeneratorTest < Rails::Generators::TestCase
       end
 
       test "does not raise if API configuration is commented out" do
-        within_api_only_app do
-          path = app_root("config/application.rb")
-          content = File.binread(path).gsub!("config.api_only = true", "# config.api_only = true")
-          File.binwrite(path, content)
-
+        within_api_only_app commented_out: true do
           run_generator
 
           assert_file app_root("Gemfile") do |file|
diff --git a/test/generators/suspenders/styles_generator_test.rb b/test/generators/suspenders/styles_generator_test.rb
new file mode 100644
index 000000000..a3980d264
--- /dev/null
+++ b/test/generators/suspenders/styles_generator_test.rb
@@ -0,0 +1,213 @@
+require "test_helper"
+require "generators/suspenders/styles_generator"
+
+module Suspenders
+  module Generators
+    class StylesGenerator::DefaultTest < Rails::Generators::TestCase
+      include Suspenders::TestHelpers
+
+      tests Suspenders::Generators::StylesGenerator
+      destination Rails.root
+      setup :prepare_destination
+      teardown :restore_destination
+
+      test "raises if API only application" do
+        within_api_only_app do
+          assert_raises Suspenders::Generators::APIAppUnsupported::Error do
+            run_generator
+          end
+        end
+      end
+
+      test "does not raise if API configuration is commented out" do
+        within_api_only_app(commented_out: true) do
+          run_generator
+        end
+      end
+
+      test "adds gems to Gemfile" do
+        run_generator
+
+        assert_file app_root("Gemfile") do |file|
+          assert_match "cssbundling-rails", file
+        end
+      end
+
+      test "installs gems with Bundler" do
+        output = run_generator
+
+        assert_match(/bundle install/, output)
+      end
+
+      test "runs install script" do
+        output = run_generator
+
+        assert_match(/bin\/rails css:install:postcss/, output)
+      end
+
+      test "generator has a description" do
+        description = <<~TEXT
+          Configures applications to use PostCSS or Tailwind via cssbundling-rails.
+          Defaults to PostCSS with modern-normalize, with the option to override via
+          --css=tailwind.
+
+          Also creates a directory structure to store additional stylesheets if using
+          PostCSS.
+        TEXT
+
+        assert_equal description, generator_class.desc
+      end
+
+      private
+
+      def prepare_destination
+        touch "Gemfile"
+        touch "app/assets/stylesheets/application.postcss.css"
+      end
+
+      def restore_destination
+        remove_file_if_exists "Gemfile"
+        remove_file_if_exists "package.json", root: true
+        remove_file_if_exists "yarn.lock", root: true
+        remove_file_if_exists "app/assets/stylesheets/application.postcss.css"
+        remove_file_if_exists "app/assets/stylesheets/base.css"
+        remove_file_if_exists "app/assets/stylesheets/components.css"
+        remove_file_if_exists "app/assets/stylesheets/utilities.css"
+      end
+    end
+
+    class StylesGenerator::ClassOptionTest < Rails::Generators::TestCase
+      include Suspenders::TestHelpers
+
+      tests Suspenders::Generators::StylesGenerator
+      destination Rails.root
+      setup :prepare_destination
+      teardown :restore_destination
+
+      test "has a css option" do
+        option = generator_class.class_options[:css]
+
+        assert_equal :string, option.type
+        assert_not option.required
+        assert_equal %w[tailwind postcss], option.enum
+        assert_equal "postcss", option.default
+      end
+
+      test "raises if css option is unsupported" do
+        output = capture(:stderr) { run_generator %w[--css=unknown] }
+
+        assert_match(/Expected '--css' to be one of/, output)
+      end
+
+      private
+
+      def prepare_destination
+        touch "Gemfile"
+      end
+
+      def restore_destination
+        remove_file_if_exists "Gemfile"
+        remove_file_if_exists "package.json", root: true
+        remove_file_if_exists "yarn.lock", root: true
+        remove_file_if_exists "app/assets/stylesheets/application.postcss.css"
+        remove_file_if_exists "app/assets/stylesheets/base.css"
+        remove_file_if_exists "app/assets/stylesheets/components.css"
+        remove_file_if_exists "app/assets/stylesheets/utilities.css"
+      end
+    end
+
+    class StylesGenerator::TailwindTest < Rails::Generators::TestCase
+      include Suspenders::TestHelpers
+
+      tests Suspenders::Generators::StylesGenerator
+      destination Rails.root
+      setup :prepare_destination
+      teardown :restore_destination
+
+      test "runs install script" do
+        output = run_generator %w[--css=tailwind]
+
+        assert_match(/bin\/rails css:install:tailwind/, output)
+      end
+
+      test "does not install normalize" do
+        output = run_generator %w[--css=tailwind]
+
+        assert_no_match(/add.*modern-normalize/, output)
+      end
+
+      test "does not create directory structure" do
+        run_generator %w[--css=tailwind]
+
+        assert_no_file app_root("app/assets/stylesheets/base.css")
+        assert_no_file app_root("app/assets/stylesheets/components.css")
+        assert_no_file app_root("app/assets/stylesheets/utilities.css")
+      end
+
+      private
+
+      def prepare_destination
+        touch "Gemfile"
+      end
+
+      def restore_destination
+        remove_file_if_exists "Gemfile"
+        remove_file_if_exists "package.json", root: true
+        remove_file_if_exists "yarn.lock", root: true
+        remove_file_if_exists "app/assets/stylesheets/base.css"
+        remove_file_if_exists "app/assets/stylesheets/components.css"
+        remove_file_if_exists "app/assets/stylesheets/utilities.css"
+      end
+    end
+
+    class StylesGenerator::PostCssTest < Rails::Generators::TestCase
+      include Suspenders::TestHelpers
+
+      tests Suspenders::Generators::StylesGenerator
+      destination Rails.root
+      setup :prepare_destination
+      teardown :restore_destination
+
+      test "installs normalize and imports style sheets" do
+        output = run_generator %w[--css=postcss]
+        application_stylesheet = <<~TEXT
+          @import "modern-normalize";
+          @import "base.css";
+          @import "components.css";
+          @import "utilities.css";
+        TEXT
+
+        assert_match(/add.*modern-normalize/, output)
+
+        assert_file app_root("app/assets/stylesheets/application.postcss.css") do |file|
+          assert_equal application_stylesheet, file
+        end
+      end
+
+      test "creates directory structure" do
+        run_generator
+
+        assert_file app_root("app/assets/stylesheets/base.css")
+        assert_file app_root("app/assets/stylesheets/components.css")
+        assert_file app_root("app/assets/stylesheets/utilities.css")
+      end
+
+      private
+
+      def prepare_destination
+        touch "Gemfile"
+        touch "app/assets/stylesheets/application.postcss.css"
+      end
+
+      def restore_destination
+        remove_file_if_exists "Gemfile"
+        remove_file_if_exists "package.json", root: true
+        remove_file_if_exists "yarn.lock", root: true
+        remove_file_if_exists "app/assets/stylesheets/application.postcss.css"
+        remove_file_if_exists "app/assets/stylesheets/base.css"
+        remove_file_if_exists "app/assets/stylesheets/components.css"
+        remove_file_if_exists "app/assets/stylesheets/utilities.css"
+      end
+    end
+  end
+end
diff --git a/test/test_helper.rb b/test/test_helper.rb
index 3fb50d589..4fcaa7ebc 100644
--- a/test/test_helper.rb
+++ b/test/test_helper.rb
@@ -19,8 +19,9 @@ def app_root(path)
     Rails.root.join path
   end
 
-  def remove_file_if_exists(file)
-    path = app_root file
+  def remove_file_if_exists(file, **options)
+    root = options[:root]
+    path = root ? file : app_root(file)
 
     FileUtils.rm path if File.exist? path
   end
@@ -43,7 +44,14 @@ def touch(file)
     FileUtils.touch path
   end
 
-  def within_api_only_app(&block)
+  def within_api_only_app(**options, &block)
+    commented_out = options[:commented_out]
+    set_config = if commented_out == true
+      "# config.api_only = true"
+    else
+      "config.api_only = true"
+    end
+
     backup_file "config/application.rb"
     application_config = <<~RUBY
       require_relative "boot"
@@ -57,7 +65,7 @@ class Application < Rails::Application
 
           config.autoload_lib(ignore: %w(assets tasks))
 
-          config.api_only = true
+          #{set_config}
         end
       end
     RUBY