diff --git a/rich/_windows.py b/rich/_windows.py
new file mode 100644
index 00000000..ef2e9204
--- /dev/null
+++ b/rich/_windows.py
@@ -0,0 +1,64 @@
+import sys
+
+from dataclasses import dataclass
+
+
+@dataclass
+class WindowsConsoleFeatures:
+    """Windows features available."""
+
+    vt: bool
+    truecolor: bool
+
+
+try:
+    import ctypes
+    from ctypes import wintypes
+    from ctypes import LibraryLoader
+
+    windll = LibraryLoader(ctypes.WinDLL)
+except (AttributeError, ImportError):
+
+    # Fallback if we can't load the Windows DLL
+    def get_windows_console_features() -> WindowsConsoleFeatures:
+        features = WindowsConsoleFeatures()
+        return features
+
+
+else:
+
+    STDOUT = -11
+    ENABLE_VIRTUAL_TERMINAL_PROCESSING = 4
+    _GetConsoleMode = windll.kernel32.GetConsoleMode
+    _GetConsoleMode.argtypes = [wintypes.HANDLE, wintypes.LPDWORD]
+    _GetConsoleMode.restype = wintypes.BOOL
+
+    _GetStdHandle = windll.kernel32.GetStdHandle
+    _GetStdHandle.argtypes = [
+        wintypes.DWORD,
+    ]
+    _GetStdHandle.restype = wintypes.HANDLE
+
+    def get_windows_console_features() -> WindowsConsoleFeatures:
+        """Get windows console fatures.
+
+        Returns:
+            WindowsConsoleFeatures: An instance of WindowsConsoleFeatures.
+        """
+        handle = _GetStdHandle(STDOUT)
+        console_mode = wintypes.DWORD()
+        result = _GetConsoleMode(handle, console_mode)
+        vt = bool(result and console_mode.value & ENABLE_VIRTUAL_TERMINAL_PROCESSING)
+        truecolor = False
+        if vt:
+            win_version = sys.getwindowsversion()
+            truecolor = win_version.major > 10 or (
+                win_version.major == 10 and win_version.build > 15063
+            )
+        features = WindowsConsoleFeatures(vt=vt, truecolor=truecolor)
+        return features
+
+
+if __name__ == "__main__":
+    print(get_windows_console_features())
+
diff --git a/rich/console.py b/rich/console.py
index 6119ef89..78efe71b 100644
--- a/rich/console.py
+++ b/rich/console.py
@@ -21,6 +21,7 @@ from typing import (
     Iterable,
     List,
     Optional,
+    TYPE_CHECKING,
     NamedTuple,
     Union,
 )
@@ -44,6 +45,8 @@ from .segment import Segment
 from .text import Text, TextType
 from .theme import Theme
 
+if TYPE_CHECKING:
+    from ._windows import WindowsConsoleFeatures
 
 WINDOWS = platform.system() == "Windows"
 
@@ -244,9 +247,22 @@ class RenderHook:
         return renderables
 
 
+_windows_console_features: Optional["WindowsConsoleFeatures"] = None
+
+
+def get_windows_console_features() -> "WindowsConsoleFeatures":
+    global _windows_console_features
+    if _windows_console_features is not None:
+        return _windows_console_features
+    from ._windows import get_windows_console_features
+
+    _windows_console_features = get_windows_console_features()
+    return _windows_console_features
+
+
 def detect_legacy_windows() -> bool:
     """Detect legacy Windows."""
-    return "WINDIR" in os.environ and "WT_SESSION" not in os.environ
+    return WINDOWS and not get_windows_console_features().vt
 
 
 if detect_legacy_windows():  # pragma: no cover
@@ -364,19 +380,26 @@ class Console:
 
     def _detect_color_system(self) -> Optional[ColorSystem]:
         """Detect color system from env vars."""
-        if not self.is_terminal:
+        if not self.is_terminal or "NO_COLOR" in os.environ:
             return None
-        if self.legacy_windows:  # pragma: no cover
-            return ColorSystem.WINDOWS
-        if "WT_SESSION" in os.environ:
-            # Exception for Windows terminal
-            return ColorSystem.TRUECOLOR
-        color_term = os.environ.get("COLORTERM", "").strip().lower()
-        return (
-            ColorSystem.TRUECOLOR
-            if color_term in ("truecolor", "24bit")
-            else ColorSystem.EIGHT_BIT
-        )
+        if WINDOWS:  # pragma: no cover
+            if self.legacy_windows:  # pragma: no cover
+                return ColorSystem.WINDOWS
+            windows_console_features = get_windows_console_features()
+            return (
+                ColorSystem.TRUECOLOR
+                if windows_console_features.truecolor
+                else ColorSystem.EIGHT_BIT
+            )
+        else:
+            if self.is_jupyter:
+                return ColorSystem.TRUECOLOR
+            color_term = os.environ.get("COLORTERM", "").strip().lower()
+            return (
+                ColorSystem.TRUECOLOR
+                if color_term in ("truecolor", "24bit")
+                else ColorSystem.EIGHT_BIT
+            )
 
     def _enter_buffer(self) -> None:
         """Enter in to a buffer context, and buffer all output."""
diff --git a/rich/style.py b/rich/style.py
index cf46a684..1277ddd8 100644
--- a/rich/style.py
+++ b/rich/style.py
@@ -247,9 +247,9 @@ class Style:
                     for bit in range(9, 13):
                         if attributes & (1 << bit):
                             append(_style_map[bit])
-            if self._color is not None:
+            if self._color is not None and color_system:
                 sgr.extend(self._color.downgrade(color_system).get_ansi_codes())
-            if self._bgcolor is not None:
+            if self._bgcolor is not None and color_system:
                 sgr.extend(
                     self._bgcolor.downgrade(color_system).get_ansi_codes(
                         foreground=False