diff --git a/Cargo.lock b/Cargo.lock
index 9c4509d77..82b308616 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -471,6 +471,11 @@ dependencies = [
  "vcpkg 0.2.6 (registry+https://github.com/rust-lang/crates.io-index)",
 ]
 
+[[package]]
+name = "path-slash"
+version = "0.1.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+
 [[package]]
 name = "percent-encoding"
 version = "2.0.0"
@@ -719,6 +724,7 @@ dependencies = [
  "git2 0.9.2 (registry+https://github.com/rust-lang/crates.io-index)",
  "lazy_static 1.3.0 (registry+https://github.com/rust-lang/crates.io-index)",
  "log 0.4.7 (registry+https://github.com/rust-lang/crates.io-index)",
+ "path-slash 0.1.1 (registry+https://github.com/rust-lang/crates.io-index)",
  "pretty_env_logger 0.3.0 (registry+https://github.com/rust-lang/crates.io-index)",
  "rayon 1.1.0 (registry+https://github.com/rust-lang/crates.io-index)",
  "serde_json 1.0.40 (registry+https://github.com/rust-lang/crates.io-index)",
@@ -986,6 +992,7 @@ dependencies = [
 "checksum numtoa 0.1.0 (registry+https://github.com/rust-lang/crates.io-index)" = "b8f8bdf33df195859076e54ab11ee78a1b208382d3a26ec40d142ffc1ecc49ef"
 "checksum openssl-probe 0.1.2 (registry+https://github.com/rust-lang/crates.io-index)" = "77af24da69f9d9341038eba93a073b1fdaaa1b788221b00a69bce9e762cb32de"
 "checksum openssl-sys 0.9.46 (registry+https://github.com/rust-lang/crates.io-index)" = "05636e06b4f8762d4b81d24a351f3966f38bd25ccbcfd235606c91fdb82cc60f"
+"checksum path-slash 0.1.1 (registry+https://github.com/rust-lang/crates.io-index)" = "a0858af4d9136275541f4eac7be1af70add84cf356d901799b065ac1b8ff6e2f"
 "checksum percent-encoding 2.0.0 (registry+https://github.com/rust-lang/crates.io-index)" = "ba4f28a6faf4ffea762ba8f4baef48c61a6db348647c73095034041fc79dd954"
 "checksum pkg-config 0.3.14 (registry+https://github.com/rust-lang/crates.io-index)" = "676e8eb2b1b4c9043511a9b7bea0915320d7e502b0a079fb03f9635a5252b18c"
 "checksum ppv-lite86 0.2.5 (registry+https://github.com/rust-lang/crates.io-index)" = "e3cbf9f658cdb5000fcf6f362b8ea2ba154b9f146a61c7a20d647034c6b6561b"
diff --git a/Cargo.toml b/Cargo.toml
index fb167f6b3..f690d0ff1 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -32,6 +32,7 @@ pretty_env_logger = "0.3.0"
 log = "0.4.7"
 battery = "0.7.4"
 lazy_static = "1.3.0"
+path-slash = "0.1.1"
 
 [dev-dependencies]
 tempfile = "3.1.0"
diff --git a/src/modules/directory.rs b/src/modules/directory.rs
index bd9d8333b..61937e751 100644
--- a/src/modules/directory.rs
+++ b/src/modules/directory.rs
@@ -1,4 +1,5 @@
 use ansi_term::Color;
+use path_slash::PathExt;
 use std::path::Path;
 
 use super::{Context, Module};
@@ -51,25 +52,43 @@ pub fn module<'a>(context: &'a Context) -> Option<Module<'a>> {
 /// `top_level_replacement`.
 fn contract_path(full_path: &Path, top_level_path: &Path, top_level_replacement: &str) -> String {
     if !full_path.starts_with(top_level_path) {
-        return full_path.to_str().unwrap().to_string();
+        return replace_c_dir(full_path.to_slash().unwrap());
     }
 
     if full_path == top_level_path {
-        return top_level_replacement.to_string();
+        return replace_c_dir(top_level_replacement.to_string());
     }
 
     format!(
         "{replacement}{separator}{path}",
         replacement = top_level_replacement,
         separator = "/",
-        path = full_path
-            .strip_prefix(top_level_path)
-            .unwrap()
-            .to_str()
-            .unwrap()
+        path = replace_c_dir(
+            full_path
+                .strip_prefix(top_level_path)
+                .unwrap()
+                .to_slash()
+                .unwrap()
+        )
     )
 }
 
+/// Replaces "C://" with "/c/" within a Windows path
+///
+/// On non-Windows OS, does nothing
+#[cfg(target_os = "windows")]
+fn replace_c_dir(path: String) -> String {
+    return path.replace("C:/", "/c");
+}
+
+/// Replaces "C://" with "/c/" within a Windows path
+///
+/// On non-Windows OS, does nothing
+#[cfg(not(target_os = "windows"))]
+fn replace_c_dir(path: String) -> String {
+    return path;
+}
+
 /// Truncate a path to only have a set number of path components
 ///
 /// Will truncate a path to only show the last `length` components in a path.
@@ -110,6 +129,46 @@ mod tests {
         assert_eq!(output, "rocket-controls/src");
     }
 
+    #[test]
+    #[cfg(target_os = "windows")]
+    fn contract_windows_style_home_directory() {
+        let full_path = Path::new("C:\\Users\\astronaut\\schematics\\rocket");
+        let home = Path::new("C:\\Users\\astronaut");
+
+        let output = contract_path(full_path, home, "~");
+        assert_eq!(output, "~/schematics/rocket");
+    }
+
+    #[test]
+    #[cfg(target_os = "windows")]
+    fn contract_windows_style_repo_directory() {
+        let full_path = Path::new("C:\\Users\\astronaut\\dev\\rocket-controls\\src");
+        let repo_root = Path::new("C:\\Users\\astronaut\\dev\\rocket-controls");
+
+        let output = contract_path(full_path, repo_root, "rocket-controls");
+        assert_eq!(output, "rocket-controls/src");
+    }
+
+    #[test]
+    #[cfg(target_os = "windows")]
+    fn contract_windows_style_no_top_level_directory() {
+        let full_path = Path::new("C:\\Some\\Other\\Path");
+        let top_level_path = Path::new("C:\\Users\\astronaut");
+
+        let output = contract_path(full_path, top_level_path, "~");
+        assert_eq!(output, "/c/Some/Other/Path");
+    }
+
+    #[test]
+    #[cfg(target_os = "windows")]
+    fn contract_windows_style_root_directory() {
+        let full_path = Path::new("C:\\");
+        let top_level_path = Path::new("C:\\Users\\astronaut");
+
+        let output = contract_path(full_path, top_level_path, "~");
+        assert_eq!(output, "/c");
+    }
+
     #[test]
     fn truncate_smaller_path_than_provided_length() {
         let path = "~/starship";