diff --git a/helix-term/src/application.rs b/helix-term/src/application.rs
index 499732f00..1da2a700d 100644
--- a/helix-term/src/application.rs
+++ b/helix-term/src/application.rs
@@ -157,7 +157,7 @@ impl Application {
 
             // If the first file is a directory, skip it and open a picker
             if let Some((first, _)) = files_it.next_if(|(p, _)| p.is_dir()) {
-                let picker = ui::file_picker(first, &config.load().editor);
+                let picker = ui::file_picker(&editor, first);
                 compositor.push(Box::new(overlaid(picker)));
             }
 
diff --git a/helix-term/src/commands.rs b/helix-term/src/commands.rs
index 1fb27a39b..a95e2a900 100644
--- a/helix-term/src/commands.rs
+++ b/helix-term/src/commands.rs
@@ -1344,7 +1344,7 @@ fn goto_file_impl(cx: &mut Context, action: Action) {
         let path = path::expand(&sel);
         let path = &rel_path.join(path);
         if path.is_dir() {
-            let picker = ui::file_picker(path.into(), &cx.editor.config());
+            let picker = ui::file_picker(cx.editor, path.into());
             cx.push_layer(Box::new(overlaid(picker)));
         } else if let Err(e) = cx.editor.open(path, action) {
             cx.editor.set_error(format!("Open file failed: {:?}", e));
@@ -1381,7 +1381,7 @@ fn open_url(cx: &mut Context, url: Url, action: Action) {
         Ok(_) | Err(_) => {
             let path = &rel_path.join(url.path());
             if path.is_dir() {
-                let picker = ui::file_picker(path.into(), &cx.editor.config());
+                let picker = ui::file_picker(cx.editor, path.into());
                 cx.push_layer(Box::new(overlaid(picker)));
             } else if let Err(e) = cx.editor.open(path, action) {
                 cx.editor.set_error(format!("Open file failed: {:?}", e));
@@ -3001,7 +3001,7 @@ fn file_picker(cx: &mut Context) {
         cx.editor.set_error("Workspace directory does not exist");
         return;
     }
-    let picker = ui::file_picker(root, &cx.editor.config());
+    let picker = ui::file_picker(cx.editor, root);
     cx.push_layer(Box::new(overlaid(picker)));
 }
 
@@ -3018,7 +3018,7 @@ fn file_picker_in_current_buffer_directory(cx: &mut Context) {
         }
     };
 
-    let picker = ui::file_picker(path, &cx.editor.config());
+    let picker = ui::file_picker(cx.editor, path);
     cx.push_layer(Box::new(overlaid(picker)));
 }
 
@@ -3029,7 +3029,7 @@ fn file_picker_in_current_directory(cx: &mut Context) {
             .set_error("Current working directory does not exist");
         return;
     }
-    let picker = ui::file_picker(cwd, &cx.editor.config());
+    let picker = ui::file_picker(cx.editor, cwd);
     cx.push_layer(Box::new(overlaid(picker)));
 }
 
diff --git a/helix-term/src/commands/typed.rs b/helix-term/src/commands/typed.rs
index 7ec594874..3953457c9 100644
--- a/helix-term/src/commands/typed.rs
+++ b/helix-term/src/commands/typed.rs
@@ -119,7 +119,7 @@ fn open(cx: &mut compositor::Context, args: &[Cow<str>], event: PromptEvent) ->
             let callback = async move {
                 let call: job::Callback = job::Callback::EditorCompositor(Box::new(
                     move |editor: &mut Editor, compositor: &mut Compositor| {
-                        let picker = ui::file_picker(path.into_owned(), &editor.config());
+                        let picker = ui::file_picker(editor, path.into_owned());
                         compositor.push(Box::new(overlaid(picker)));
                     },
                 ));
diff --git a/helix-term/src/ui/mod.rs b/helix-term/src/ui/mod.rs
index 21a68d7f8..a76adbe21 100644
--- a/helix-term/src/ui/mod.rs
+++ b/helix-term/src/ui/mod.rs
@@ -30,7 +30,7 @@ pub use spinner::{ProgressSpinners, Spinner};
 pub use text::Text;
 
 use helix_view::Editor;
-use tui::text::Span;
+use tui::text::{Span, Spans};
 
 use std::path::Path;
 use std::{error::Error, path::PathBuf};
@@ -185,12 +185,23 @@ pub fn raw_regex_prompt(
     cx.push_layer(Box::new(prompt));
 }
 
-type FilePicker = Picker<PathBuf, PathBuf>;
+#[derive(Debug)]
+pub struct FilePickerData {
+    root: PathBuf,
+    directory_style: Style,
+}
+type FilePicker = Picker<PathBuf, FilePickerData>;
 
-pub fn file_picker(root: PathBuf, config: &helix_view::editor::Config) -> FilePicker {
+pub fn file_picker(editor: &Editor, root: PathBuf) -> FilePicker {
     use ignore::{types::TypesBuilder, WalkBuilder};
     use std::time::Instant;
 
+    let config = editor.config();
+    let data = FilePickerData {
+        root: root.clone(),
+        directory_style: editor.theme.get("ui.text.directory"),
+    };
+
     let now = Instant::now();
 
     let dedup_symlinks = config.file_picker.deduplicate_links;
@@ -236,14 +247,24 @@ pub fn file_picker(root: PathBuf, config: &helix_view::editor::Config) -> FilePi
 
     let columns = [PickerColumn::new(
         "path",
-        |item: &PathBuf, root: &PathBuf| {
-            item.strip_prefix(root)
-                .unwrap_or(item)
-                .to_string_lossy()
-                .into()
+        |item: &PathBuf, data: &FilePickerData| {
+            let path = item.strip_prefix(&data.root).unwrap_or(item);
+            let mut spans = Vec::with_capacity(3);
+            if let Some(dirs) = path.parent().filter(|p| !p.as_os_str().is_empty()) {
+                spans.extend([
+                    Span::styled(dirs.to_string_lossy(), data.directory_style),
+                    Span::styled(std::path::MAIN_SEPARATOR_STR, data.directory_style),
+                ]);
+            }
+            let filename = path
+                .file_name()
+                .expect("normalized paths can't end in `..`")
+                .to_string_lossy();
+            spans.push(Span::raw(filename));
+            Spans::from(spans).into()
         },
     )];
-    let picker = Picker::new(columns, 0, [], root, move |cx, path: &PathBuf, action| {
+    let picker = Picker::new(columns, 0, [], data, move |cx, path: &PathBuf, action| {
         if let Err(e) = cx.editor.open(path, action) {
             let err = if let Some(err) = e.source() {
                 format!("{}", err)