diff --git a/libcxx/include/__filesystem/directory_entry.h b/libcxx/include/__filesystem/directory_entry.h
--- a/libcxx/include/__filesystem/directory_entry.h
+++ b/libcxx/include/__filesystem/directory_entry.h
@@ -23,6 +23,7 @@
 #include <chrono>
 #include <cstdint>
 #include <cstdlib>
+#include <ostream>
 #include <system_error>
 
 _LIBCPP_PUSH_MACROS
@@ -239,6 +240,12 @@
     return __p_ >= __rhs.__p_;
   }
 
+  template <class _CharT, class _Traits>
+  _LIBCPP_INLINE_VISIBILITY
+  friend basic_ostream<_CharT, _Traits>& operator<<(basic_ostream<_CharT, _Traits>& __os, const directory_entry& __d) {
+    return __os << __d.path();
+  }
+
 private:
   friend class directory_iterator;
   friend class recursive_directory_iterator;
diff --git a/libcxx/include/filesystem b/libcxx/include/filesystem
--- a/libcxx/include/filesystem
+++ b/libcxx/include/filesystem
@@ -42,8 +42,14 @@
       path u8path(InputIterator first, InputIterator last);
 
     class filesystem_error;
+
     class directory_entry;
 
+    // The fs.dir.entry.io operator is a friend of directory_entry.
+    template<class charT, class traits>
+      friend basic_ostream<charT, traits>&
+        operator<<(basic_ostream<charT, traits>& os, const directory_entry& d);
+
     class directory_iterator;
 
     // enable directory_iterator range-based for statements
diff --git a/libcxx/test/std/input.output/filesystems/class.directory_entry/directory_entry.io/directory_entry.io.pass.cpp b/libcxx/test/std/input.output/filesystems/class.directory_entry/directory_entry.io/directory_entry.io.pass.cpp
new file mode 100644
--- /dev/null
+++ b/libcxx/test/std/input.output/filesystems/class.directory_entry/directory_entry.io/directory_entry.io.pass.cpp
@@ -0,0 +1,56 @@
+//===----------------------------------------------------------------------===//
+//
+// Part of the LLVM Project, under the Apache License v2.0 with LLVM Exceptions.
+// See https://llvm.org/LICENSE.txt for license information.
+// SPDX-License-Identifier: Apache-2.0 WITH LLVM-exception
+//
+//===----------------------------------------------------------------------===//
+
+// UNSUPPORTED: c++03
+// UNSUPPORTED: libcpp-has-no-localization
+
+// <filesystem>
+//
+// class directory_entry
+//
+// template<class charT, class traits>
+//   friend basic_ostream<charT, traits>&
+//     operator<<(basic_ostream<charT, traits>& os, const directory_entry& d);
+
+#include "filesystem_include.h"
+#include <cassert>
+#include <sstream>
+
+#include "test_macros.h"
+#include "make_string.h"
+
+MultiStringType InStr =  MKSTR("abcdefg/\"hijklmnop\"/qrstuvwxyz/123456789");
+MultiStringType OutStr = MKSTR("\"abcdefg/\\\"hijklmnop\\\"/qrstuvwxyz/123456789\"");
+
+template <class CharT>
+void TestOutput() {
+  using namespace fs;
+
+  const char* input = static_cast<const char*>(InStr);
+  const CharT* expected_output = static_cast<const CharT*>(OutStr);
+  path p(input);
+  std::basic_stringstream<CharT> stream;
+
+  auto& result = stream << p;
+  assert(stream.str() == expected_output);
+  assert(&result == &stream);
+}
+
+int main(int, char**) {
+  TestOutput<char>();
+#ifndef TEST_HAS_NO_WIDE_CHARACTERS
+  TestOutput<wchar_t>();
+#endif
+  // TODO(var-const): uncomment when it becomes possible to instantiate a `basic_ostream` object with a sized character
+  // type. Currently the instantiation would fail because `ctype` only has specializations for `char` and `wchar_t`.
+  //TestOutput<char8_t>();
+  //TestOutput<char16_t>();
+  //TestOutput<char32_t>();
+
+  return 0;
+}