diff --git a/src/commands/list.rs b/src/commands/list.rs
index 03309aa..3f1fd62 100644
--- a/src/commands/list.rs
+++ b/src/commands/list.rs
@@ -11,6 +11,7 @@ pub trait ListCommand {
     out: impl Write,
     preview_width: u32,
     include_expired: bool,
+    reverse: bool,
   ) -> Result<(), StashError>;
 }
 
@@ -20,9 +21,10 @@ impl ListCommand for SqliteClipboardDb {
     out: impl Write,
     preview_width: u32,
     include_expired: bool,
+    reverse: bool,
   ) -> Result<(), StashError> {
     self
-      .list_entries(out, preview_width, include_expired)
+      .list_entries(out, preview_width, include_expired, reverse)
       .map(|_| ())
   }
 }
@@ -52,6 +54,9 @@ struct TuiState {
 
   /// Whether we're currently in search input mode.
   search_mode: bool,
+
+  /// Whether to show entries in reverse order (oldest first).
+  reverse: bool,
 }
 
 impl TuiState {
@@ -61,6 +66,7 @@ impl TuiState {
     include_expired: bool,
     window_size: usize,
     preview_width: u32,
+    reverse: bool,
   ) -> Result<Self, StashError> {
     let total = db.count_entries(include_expired, None)?;
     let window = if total > 0 {
@@ -70,6 +76,7 @@ impl TuiState {
         window_size,
         preview_width,
         None,
+        reverse,
       )?
     } else {
       Vec::new()
@@ -83,6 +90,7 @@ impl TuiState {
       dirty: false,
       search_query: String::new(),
       search_mode: false,
+      reverse,
     })
   }
 
@@ -228,6 +236,7 @@ impl TuiState {
         self.window_size,
         preview_width,
         search,
+        self.reverse,
       )?
     } else {
       Vec::new()
@@ -266,6 +275,7 @@ impl SqliteClipboardDb {
     &self,
     preview_width: u32,
     include_expired: bool,
+    reverse: bool,
   ) -> Result<(), StashError> {
     use std::io::stdout;
 
@@ -316,8 +326,13 @@ impl SqliteClipboardDb {
       .unwrap_or(24);
     let initial_height = initial_height.max(1);
 
-    let mut tui =
-      TuiState::new(self, include_expired, initial_height, preview_width)?;
+    let mut tui = TuiState::new(
+      self,
+      include_expired,
+      initial_height,
+      preview_width,
+      reverse,
+    )?;
 
     // ratatui ListState; only tracks selection within the *window* slice.
     let mut list_state = ListState::default();
diff --git a/src/db/mod.rs b/src/db/mod.rs
index 5bbfffb..2c3921f 100644
--- a/src/db/mod.rs
+++ b/src/db/mod.rs
@@ -89,6 +89,7 @@ pub trait ClipboardDb {
     out: impl Write,
     preview_width: u32,
     include_expired: bool,
+    reverse: bool,
   ) -> Result<usize, StashError>;
   fn decode_entry(
     &self,
@@ -362,17 +363,27 @@ impl SqliteClipboardDb {
 }
 
 impl SqliteClipboardDb {
-  pub fn list_json(&self, include_expired: bool) -> Result<String, StashError> {
+  pub fn list_json(
+    &self,
+    include_expired: bool,
+    reverse: bool,
+  ) -> Result<String, StashError> {
+    let order = if reverse { "ASC" } else { "DESC" };
     let query = if include_expired {
-      "SELECT id, contents, mime FROM clipboard ORDER BY \
-       COALESCE(last_accessed, 0) DESC, id DESC"
+      format!(
+        "SELECT id, contents, mime FROM clipboard ORDER BY \
+         COALESCE(last_accessed, 0) {order}, id {order}"
+      )
     } else {
-      "SELECT id, contents, mime FROM clipboard WHERE (is_expired IS NULL OR \
-       is_expired = 0) ORDER BY COALESCE(last_accessed, 0) DESC, id DESC"
+      format!(
+        "SELECT id, contents, mime FROM clipboard WHERE (is_expired IS NULL \
+         OR is_expired = 0) ORDER BY COALESCE(last_accessed, 0) {order}, id \
+         {order}"
+      )
     };
     let mut stmt = self
       .conn
-      .prepare(query)
+      .prepare(&query)
       .map_err(|e| StashError::ListDecode(e.to_string().into()))?;
     let mut rows = stmt
       .query([])
@@ -594,17 +605,24 @@ impl ClipboardDb for SqliteClipboardDb {
     mut out: impl Write,
     preview_width: u32,
     include_expired: bool,
+    reverse: bool,
   ) -> Result<usize, StashError> {
+    let order = if reverse { "ASC" } else { "DESC" };
     let query = if include_expired {
-      "SELECT id, contents, mime FROM clipboard ORDER BY \
-       COALESCE(last_accessed, 0) DESC, id DESC"
+      format!(
+        "SELECT id, contents, mime FROM clipboard ORDER BY \
+         COALESCE(last_accessed, 0) {order}, id {order}"
+      )
     } else {
-      "SELECT id, contents, mime FROM clipboard WHERE (is_expired IS NULL OR \
-       is_expired = 0) ORDER BY COALESCE(last_accessed, 0) DESC, id DESC"
+      format!(
+        "SELECT id, contents, mime FROM clipboard WHERE (is_expired IS NULL \
+         OR is_expired = 0) ORDER BY COALESCE(last_accessed, 0) {order}, id \
+         {order}"
+      )
     };
     let mut stmt = self
       .conn
-      .prepare(query)
+      .prepare(&query)
       .map_err(|e| StashError::ListDecode(e.to_string().into()))?;
     let mut rows = stmt
       .query([])
@@ -818,38 +836,48 @@ impl SqliteClipboardDb {
     limit: usize,
     preview_width: u32,
     search: Option<&str>,
+    reverse: bool,
   ) -> Result<Vec<(i64, String, String)>, StashError> {
     let search_pattern = search.map(|s| {
       let escaped = s.replace('!', "!!").replace('%', "!%").replace('_', "!_");
       format!("%{escaped}%")
     });
 
+    let order = if reverse { "ASC" } else { "DESC" };
     let query = match (include_expired, search_pattern.as_deref()) {
       (true, None) => {
-        "SELECT id, contents, mime FROM clipboard ORDER BY \
-         COALESCE(last_accessed, 0) DESC, id DESC LIMIT ?1 OFFSET ?2"
+        format!(
+          "SELECT id, contents, mime FROM clipboard ORDER BY \
+           COALESCE(last_accessed, 0) {order}, id {order} LIMIT ?1 OFFSET ?2"
+        )
       },
       (true, Some(_)) => {
-        "SELECT id, contents, mime FROM clipboard WHERE (LOWER(CAST(contents \
-         AS TEXT)) LIKE LOWER(?3) ESCAPE '!') ORDER BY COALESCE(last_accessed, \
-         0) DESC, id DESC LIMIT ?1 OFFSET ?2"
+        format!(
+          "SELECT id, contents, mime FROM clipboard WHERE \
+           (LOWER(CAST(contents AS TEXT)) LIKE LOWER(?3) ESCAPE '!') ORDER BY \
+           COALESCE(last_accessed, 0) {order}, id {order} LIMIT ?1 OFFSET ?2"
+        )
       },
       (false, None) => {
-        "SELECT id, contents, mime FROM clipboard WHERE (is_expired IS NULL OR \
-         is_expired = 0) ORDER BY COALESCE(last_accessed, 0) DESC, id DESC \
-         LIMIT ?1 OFFSET ?2"
+        format!(
+          "SELECT id, contents, mime FROM clipboard WHERE (is_expired IS NULL \
+           OR is_expired = 0) ORDER BY COALESCE(last_accessed, 0) {order}, id \
+           {order} LIMIT ?1 OFFSET ?2"
+        )
       },
       (false, Some(_)) => {
-        "SELECT id, contents, mime FROM clipboard WHERE (is_expired IS NULL OR \
-         is_expired = 0) AND (LOWER(CAST(contents AS TEXT)) LIKE LOWER(?3) \
-         ESCAPE '!') ORDER BY COALESCE(last_accessed, 0) DESC, id DESC LIMIT \
-         ?1 OFFSET ?2"
+        format!(
+          "SELECT id, contents, mime FROM clipboard WHERE (is_expired IS NULL \
+           OR is_expired = 0) AND (LOWER(CAST(contents AS TEXT)) LIKE \
+           LOWER(?3) ESCAPE '!') ORDER BY COALESCE(last_accessed, 0) {order}, \
+           id {order} LIMIT ?1 OFFSET ?2"
+        )
       },
     };
 
     let mut stmt = self
       .conn
-      .prepare(query)
+      .prepare(&query)
       .map_err(|e| StashError::ListDecode(e.to_string().into()))?;
 
     let mut rows = if let Some(pattern) = search_pattern.as_deref() {
diff --git a/src/main.rs b/src/main.rs
index ef12ed1..fd74b1f 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -91,6 +91,10 @@ enum Command {
     /// Show only expired entries (diagnostic, does not remove them)
     #[arg(long)]
     expired: bool,
+
+    /// Reverse the order of entries (oldest first instead of newest first)
+    #[arg(long)]
+    reverse: bool,
   },
 
   /// Decode and output clipboard entry by id
@@ -245,16 +249,20 @@ fn main() -> color_eyre::eyre::Result<()> {
           "failed to store entry",
         );
       },
-      Some(Command::List { format, expired }) => {
+      Some(Command::List {
+        format,
+        expired,
+        reverse,
+      }) => {
         match format.as_deref() {
           Some("tsv") => {
             report_error(
-              db.list(io::stdout(), cli.preview_width, expired),
+              db.list(io::stdout(), cli.preview_width, expired, reverse),
               "failed to list entries",
             );
           },
           Some("json") => {
-            match db.list_json(expired) {
+            match db.list_json(expired, reverse) {
               Ok(json) => {
                 println!("{json}");
               },
@@ -269,12 +277,12 @@ fn main() -> color_eyre::eyre::Result<()> {
           None => {
             if std::io::stdout().is_terminal() {
               report_error(
-                db.list_tui(cli.preview_width, expired),
+                db.list_tui(cli.preview_width, expired, reverse),
                 "failed to list entries in TUI",
               );
             } else {
               report_error(
-                db.list(io::stdout(), cli.preview_width, expired),
+                db.list(io::stdout(), cli.preview_width, expired, reverse),
                 "failed to list entries",
               );
             }