diff --git a/include/client.hpp b/include/client.hpp
index 9ec29ef3..641ee6a7 100644
--- a/include/client.hpp
+++ b/include/client.hpp
@@ -7,6 +7,7 @@
 
 #include "bar.hpp"
 #include "config.hpp"
+#include "util/css_reload_helper.hpp"
 #include "util/portal.hpp"
 
 struct zwlr_layer_shell_v1;
@@ -55,6 +56,8 @@ class Client {
   Glib::RefPtr<Gtk::CssProvider> css_provider_;
   std::unique_ptr<Portal> portal;
   std::list<struct waybar_output> outputs_;
+  std::unique_ptr<CssReloadHelper> m_cssReloadHelper;
+  std::string m_cssFile;
 };
 
 }  // namespace waybar
diff --git a/include/util/css_reload_helper.hpp b/include/util/css_reload_helper.hpp
new file mode 100644
index 00000000..62507e42
--- /dev/null
+++ b/include/util/css_reload_helper.hpp
@@ -0,0 +1,49 @@
+#pragma once
+
+#include <atomic>
+#include <condition_variable>
+#include <functional>
+#include <mutex>
+#include <string>
+#include <thread>
+#include <vector>
+
+struct pollfd;
+
+namespace waybar {
+class CssReloadHelper {
+ public:
+  CssReloadHelper(std::string cssFile, std::function<void()> callback);
+
+  ~CssReloadHelper();
+
+  virtual void monitorChanges();
+
+  void stop();
+
+ protected:
+  std::vector<std::string> parseImports(const std::string& cssFile);
+
+  void parseImports(const std::string& cssFile,
+                           std::unordered_map<std::string, bool>& imports);
+
+
+  void watchFiles(const std::vector<std::string>& files);
+
+  bool handleInotifyEvents(int fd);
+
+  bool watch(int inotifyFd, pollfd * pollFd);
+
+  virtual std::string getFileContents(const std::string& filename);
+
+  virtual std::string findPath(const std::string& filename);
+
+ private:
+  std::string m_cssFile;
+  std::function<void()> m_callback;
+  std::atomic<bool> m_running = false;
+  std::thread m_thread;
+  std::mutex m_mutex;
+  std::condition_variable m_cv;
+};
+}  // namespace waybar
diff --git a/meson.build b/meson.build
index c1ae48b5..d7549731 100644
--- a/meson.build
+++ b/meson.build
@@ -196,7 +196,8 @@ src_files = files(
     'src/util/sanitize_str.cpp',
     'src/util/rewrite_string.cpp',
     'src/util/gtk_icon.cpp',
-    'src/util/regex_collection.cpp'
+    'src/util/regex_collection.cpp',
+    'src/util/css_reload_helper.cpp'
 )
 
 inc_dirs = ['include']
diff --git a/src/client.cpp b/src/client.cpp
index 066247e7..ff1be5d8 100644
--- a/src/client.cpp
+++ b/src/client.cpp
@@ -262,15 +262,18 @@ int waybar::Client::main(int argc, char *argv[]) {
   if (!portal) {
     portal = std::make_unique<waybar::Portal>();
   }
-  auto css_file = getStyle(style_opt);
-  setupCss(css_file);
+  m_cssFile = getStyle(style_opt);
+  setupCss(m_cssFile);
+  m_cssReloadHelper = std::make_unique<CssReloadHelper>(m_cssFile, [&]() { setupCss(m_cssFile); });
   portal->signal_appearance_changed().connect([&](waybar::Appearance appearance) {
     auto css_file = getStyle(style_opt, appearance);
     setupCss(css_file);
   });
+  m_cssReloadHelper->monitorChanges();
   bindInterfaces();
   gtk_app->hold();
   gtk_app->run();
+  m_cssReloadHelper.reset(); // stop watching css file
   bars.clear();
   return 0;
 }
diff --git a/src/util/css_reload_helper.cpp b/src/util/css_reload_helper.cpp
new file mode 100644
index 00000000..4038f1f3
--- /dev/null
+++ b/src/util/css_reload_helper.cpp
@@ -0,0 +1,214 @@
+#include "util/css_reload_helper.hpp"
+
+#include <poll.h>
+#include <spdlog/spdlog.h>
+#include <sys/inotify.h>
+
+#include <filesystem>
+#include <fstream>
+#include <regex>
+#include <unordered_map>
+
+#include "config.hpp"
+namespace {
+const std::regex IMPORT_REGEX(R"(@import\s+(?:url\()?(?:"|')([^"')]+)(?:"|')\)?;)");
+}
+
+waybar::CssReloadHelper::CssReloadHelper(std::string cssFile, std::function<void()> callback)
+    : m_cssFile(std::move(cssFile)), m_callback(std::move(callback)) {}
+
+waybar::CssReloadHelper::~CssReloadHelper() { stop(); }
+
+std::string waybar::CssReloadHelper::getFileContents(const std::string& filename) {
+  if (filename.empty()) {
+    return {};
+  }
+
+  std::ifstream file(filename);
+  if (!file.is_open()) {
+    return {};
+  }
+
+  return std::string((std::istreambuf_iterator<char>(file)), std::istreambuf_iterator<char>());
+}
+
+std::string waybar::CssReloadHelper::findPath(const std::string& filename) {
+  // try path and fallback to looking relative to the config
+  if (std::filesystem::exists(filename)) {
+    return filename;
+  }
+
+  return Config::findConfigPath({filename}).value_or("");
+}
+
+void waybar::CssReloadHelper::monitorChanges() {
+  m_thread = std::thread([this] {
+    m_running = true;
+    while (m_running) {
+      auto files = parseImports(m_cssFile);
+      watchFiles(files);
+    }
+  });
+}
+
+std::vector<std::string> waybar::CssReloadHelper::parseImports(const std::string& cssFile) {
+  std::unordered_map<std::string, bool> imports;
+
+  auto cssFullPath = findPath(cssFile);
+  if (cssFullPath.empty()) {
+    spdlog::error("Failed to find css file: {}", cssFile);
+    return {};
+  }
+
+  spdlog::debug("Parsing imports for file: {}", cssFullPath);
+  imports[cssFullPath] = false;
+
+  auto previousSize = 0UL;
+  auto maxIterations = 100U;
+  do {
+    previousSize = imports.size();
+    for (const auto& [file, parsed] : imports) {
+      if (!parsed) {
+        parseImports(file, imports);
+      }
+    }
+
+  } while (imports.size() > previousSize && maxIterations-- > 0);
+
+  std::vector<std::string> result;
+  for (const auto& [file, parsed] : imports) {
+    if (parsed) {
+      spdlog::debug("Adding file to watch list: {}", file);
+      result.push_back(file);
+    }
+  }
+
+  return result;
+}
+
+void waybar::CssReloadHelper::parseImports(const std::string& cssFile,
+                                           std::unordered_map<std::string, bool>& imports) {
+  // if the file has already been parsed, skip
+  if (imports.find(cssFile) != imports.end() && imports[cssFile]) {
+    return;
+  }
+
+  auto contents = getFileContents(cssFile);
+  std::smatch matches;
+  while (std::regex_search(contents, matches, IMPORT_REGEX)) {
+    auto importFile = findPath({matches[1].str()});
+    if (!importFile.empty() && imports.find(importFile) == imports.end()) {
+      imports[importFile] = false;
+    }
+
+    contents = matches.suffix().str();
+  }
+
+  imports[cssFile] = true;
+}
+
+void waybar::CssReloadHelper::stop() {
+  if (!m_running) {
+    return;
+  }
+
+  m_running = false;
+  m_cv.notify_all();
+  if (m_thread.joinable()) {
+    m_thread.join();
+  }
+}
+
+void waybar::CssReloadHelper::watchFiles(const std::vector<std::string>& files) {
+  auto inotifyFd = inotify_init1(IN_NONBLOCK);
+  if (inotifyFd < 0) {
+    spdlog::error("Failed to initialize inotify: {}", strerror(errno));
+    return;
+  }
+
+  std::vector<int> watchFds;
+  for (const auto& file : files) {
+    auto watchFd = inotify_add_watch(inotifyFd, file.c_str(), IN_MODIFY | IN_MOVED_TO);
+    if (watchFd < 0) {
+      spdlog::error("Failed to add watch for file: {}", file);
+    } else {
+      spdlog::debug("Added watch for file: {}", file);
+    }
+    watchFds.push_back(watchFd);
+  }
+
+  auto pollFd = pollfd{inotifyFd, POLLIN, 0};
+
+  while (true) {
+    if (watch(inotifyFd, &pollFd)) {
+      break;
+    }
+  }
+
+  for (const auto& watchFd : watchFds) {
+    inotify_rm_watch(inotifyFd, watchFd);
+  }
+
+  close(inotifyFd);
+}
+
+bool waybar::CssReloadHelper::watch(int inotifyFd, pollfd* pollFd) {
+  auto pollResult = poll(pollFd, 1, 10);
+  if (pollResult < 0) {
+    spdlog::error("Failed to poll inotify: {}", strerror(errno));
+    return true;
+  }
+
+  if (pollResult == 0) {
+    // check if we should stop
+    if (!m_running) {
+      return true;
+    }
+
+    std::unique_lock<std::mutex> lock(m_mutex);
+    // a condition variable is used to allow the thread to be stopped immediately while still not
+    // spamming poll
+    m_cv.wait_for(lock, std::chrono::milliseconds(250), [this] { return !m_running; });
+
+    // timeout
+    return false;
+  }
+
+  if (static_cast<bool>(pollFd->revents & POLLIN)) {
+    if (handleInotifyEvents(inotifyFd)) {
+      // after the callback is fired we need to re-parse the imports and setup the watches
+      // again in case the import list has changed
+      return true;
+    }
+  }
+
+  return false;
+}
+
+bool waybar::CssReloadHelper::handleInotifyEvents(int inotify_fd) {
+  // inotify event
+  auto buffer = std::array<char, 4096>{};
+  auto readResult = read(inotify_fd, buffer.data(), buffer.size());
+  if (readResult < 0) {
+    spdlog::error("Failed to read inotify event: {}", strerror(errno));
+    return false;
+  }
+
+  auto offset = 0;
+  auto shouldFireCallback = false;
+
+  // read all events on the fd
+  while (offset < readResult) {
+    auto* event = reinterpret_cast<inotify_event*>(buffer.data() + offset);
+    offset += sizeof(inotify_event) + event->len;
+    shouldFireCallback = true;
+  }
+
+  // we only need to fire the callback once
+  if (shouldFireCallback) {
+    m_callback();
+    return true;
+  }
+
+  return false;
+}
diff --git a/test/css_reload_helper.cpp b/test/css_reload_helper.cpp
new file mode 100644
index 00000000..3ee1fb6e
--- /dev/null
+++ b/test/css_reload_helper.cpp
@@ -0,0 +1,188 @@
+#include "util/css_reload_helper.hpp"
+#include <map>
+#include <fstream>
+
+#if __has_include(<catch2/catch_test_macros.hpp>)
+#include <catch2/catch_test_macros.hpp>
+#include <catch2/matchers/catch_matchers_all.hpp>
+#else
+#include <catch2/catch.hpp>
+#endif
+
+
+class CssReloadHelperTest : public waybar::CssReloadHelper
+{
+public:
+  CssReloadHelperTest()
+    : CssReloadHelper("/tmp/waybar_test.css", [this]() {callback();})
+  {
+  }
+
+  void callback()
+  {
+    m_callbackCounter++;
+  }
+
+protected:
+
+  std::string getFileContents(const std::string& filename) override
+  {
+    return m_fileContents[filename];
+  }
+
+  std::string findPath(const std::string& filename) override
+  {
+    return filename;
+  }
+
+  void setFileContents(const std::string& filename, const std::string& contents)
+  {
+    m_fileContents[filename] = contents;
+  }
+
+  int getCallbackCounter() const
+  {
+    return m_callbackCounter;
+  }
+
+private:
+  int m_callbackCounter{};
+  std::map<std::string, std::string> m_fileContents;
+};
+
+TEST_CASE_METHOD(CssReloadHelperTest, "parse_imports", "[util][css_reload_helper]")
+{
+  SECTION("no imports")
+  {
+    setFileContents("/tmp/waybar_test.css", "body { color: red; }");
+    auto files = parseImports("/tmp/waybar_test.css");
+    REQUIRE(files.size() == 1);
+    CHECK(files[0] == "/tmp/waybar_test.css");
+  }
+
+  SECTION("single import")
+  {
+    setFileContents("/tmp/waybar_test.css", "@import 'test.css';");
+    setFileContents("test.css", "body { color: red; }");
+    auto files = parseImports("/tmp/waybar_test.css");
+    std::sort(files.begin(), files.end());
+    REQUIRE(files.size() == 2);
+    CHECK(files[0] == "/tmp/waybar_test.css");
+    CHECK(files[1] == "test.css");
+  }
+
+  SECTION("multiple imports")
+  {
+    setFileContents("/tmp/waybar_test.css", "@import 'test.css'; @import 'test2.css';");
+    setFileContents("test.css", "body { color: red; }");
+    setFileContents("test2.css", "body { color: blue; }");
+    auto files = parseImports("/tmp/waybar_test.css");
+    std::sort(files.begin(), files.end());
+    REQUIRE(files.size() == 3);
+    CHECK(files[0] == "/tmp/waybar_test.css");
+    CHECK(files[1] == "test.css");
+    CHECK(files[2] == "test2.css");
+  }
+
+  SECTION("nested imports")
+  {
+    setFileContents("/tmp/waybar_test.css", "@import 'test.css';");
+    setFileContents("test.css", "@import 'test2.css';");
+    setFileContents("test2.css", "body { color: red; }");
+    auto files = parseImports("/tmp/waybar_test.css");
+    std::sort(files.begin(), files.end());
+    REQUIRE(files.size() == 3);
+    CHECK(files[0] == "/tmp/waybar_test.css");
+    CHECK(files[1] == "test.css");
+    CHECK(files[2] == "test2.css");
+  }
+
+  SECTION("circular imports")
+  {
+    setFileContents("/tmp/waybar_test.css", "@import 'test.css';");
+    setFileContents("test.css", "@import 'test2.css';");
+    setFileContents("test2.css", "@import 'test.css';");
+    auto files = parseImports("/tmp/waybar_test.css");
+    std::sort(files.begin(), files.end());
+    REQUIRE(files.size() == 3);
+    CHECK(files[0] == "/tmp/waybar_test.css");
+    CHECK(files[1] == "test.css");
+    CHECK(files[2] == "test2.css");
+  }
+
+  SECTION("empty")
+  {
+    setFileContents("/tmp/waybar_test.css", "");
+    auto files = parseImports("/tmp/waybar_test.css");
+    REQUIRE(files.size() == 1);
+    CHECK(files[0] == "/tmp/waybar_test.css");
+  }
+
+  SECTION("empty name")
+  {
+    auto files = parseImports("");
+    REQUIRE(files.empty());
+  }
+}
+
+TEST_CASE("file_watcher", "[util][css_reload_helper]")
+{
+  SECTION("file does not exist")
+  {
+    std::atomic<int> count;
+    std::string f1 = std::tmpnam(nullptr);
+    waybar::CssReloadHelper helper(f1, [&count](){++count;});
+    helper.monitorChanges();
+
+    std::this_thread::sleep_for(std::chrono::milliseconds(100));
+
+    CHECK(count == 0);
+    helper.stop();
+    std::remove(f1.c_str());
+  }
+
+  SECTION("file exists")
+  {
+    std::atomic<int> count;
+    std::string f1 = std::tmpnam(nullptr);
+    std::ofstream(f1) << "body { color: red; }";
+    waybar::CssReloadHelper helper(f1, [&count](){++count;});
+    helper.monitorChanges();
+
+    std::this_thread::sleep_for(std::chrono::milliseconds(100));
+
+    CHECK(count == 0);
+
+    std::this_thread::sleep_for(std::chrono::milliseconds(100));
+
+    std::ofstream(f1) << "body { color: blue; }";
+    std::this_thread::sleep_for(std::chrono::milliseconds(100));
+    CHECK(count == 1);
+    helper.stop();
+    std::remove(f1.c_str());
+  }
+
+  SECTION("multiple files")
+  {
+    std::atomic<int> count;
+    std::string f1 = std::tmpnam(nullptr);
+    std::string f2 = std::tmpnam(nullptr);
+    std::ofstream(f1) << ("@import '" + f2 + " ';");
+    std::ofstream(f2) << "body { color: red; }";
+    waybar::CssReloadHelper helper(f1, [&count](){++count;});
+    helper.monitorChanges();
+
+    std::this_thread::sleep_for(std::chrono::milliseconds(100));
+
+    CHECK(count == 0);
+
+    std::this_thread::sleep_for(std::chrono::milliseconds(100));
+
+    std::ofstream(f2) << "body { color: blue; }";
+    std::this_thread::sleep_for(std::chrono::milliseconds(100));
+    CHECK(count == 1);
+    helper.stop();
+    std::remove(f1.c_str());
+    std::remove(f2.c_str());
+  }
+}
diff --git a/test/meson.build b/test/meson.build
index 02cbb2a4..358d6c96 100644
--- a/test/meson.build
+++ b/test/meson.build
@@ -10,7 +10,9 @@ test_src = files(
     'main.cpp',
     'SafeSignal.cpp',
     'config.cpp',
+    'css_reload_helper.cpp',
     '../src/config.cpp',
+    '../src/util/css_reload_helper.cpp',
 )
 
 if tz_dep.found()