diff --git a/README.md b/README.md
index 234dcaf..0bc640c 100644
--- a/README.md
+++ b/README.md
@@ -368,6 +368,7 @@ for types that implement `core::fmt::Debug`:
 |----------------------------|----------------------------------------------------------------------------|
 | has_debug_string           | verify that a type formatted for debug is equal to the expected string     |                                                 
 | does_not_have_debug_string | verify that a type formatted for debug is not equal to the expected string |
+| debug_string               | map the subject to its debug string representation                         |
 
 for types that implement `core::fmt::Display`:
 
@@ -375,6 +376,7 @@ for types that implement `core::fmt::Display`:
 |------------------------------|------------------------------------------------------------------------------|
 | has_display_string           | verify that a type formatted for display is equal to the expected string     |                                                 
 | does_not_have_display_string | verify that a type formatted for display is not equal to the expected string |
+| display_string               | map the subject to its display string representation                         |
 
 ### Emptiness
 
diff --git a/src/assertions.rs b/src/assertions.rs
index cdfe63c..fa0de9b 100644
--- a/src/assertions.rs
+++ b/src/assertions.rs
@@ -2332,6 +2332,47 @@ pub trait AssertHasDebugString<E> {
     fn does_not_have_debug_string(self, expected: E) -> Self;
 }
 
+/// Mapping the subject into its debug string representation to do assertions on
+/// its debug string.
+///
+/// # Examples
+///
+/// ```
+/// use asserting::prelude::*;
+///
+/// #[derive(Debug)]
+/// struct Foo {
+///     hello: String,
+/// }
+///
+/// let subject = Foo { hello: "World".into() };
+///
+/// assert_that!(&subject).debug_string().contains("World");
+/// assert_that!(&subject).debug_string().does_not_start_with("Bar");
+/// ```
+pub trait AssertDebugString<'a, R> {
+    /// Maps the subject into its debug string representation to do assertions
+    /// on its debug string.
+    ///
+    /// # Examples
+    ///
+    /// ```
+    /// use asserting::prelude::*;
+    ///
+    /// #[derive(Debug)]
+    /// struct Foo {
+    ///     hello: String,
+    /// }
+    ///
+    /// let subject = Foo { hello: "World".into() };
+    ///
+    /// assert_that!(&subject).debug_string().contains("World");
+    /// assert_that!(&subject).debug_string().does_not_start_with("Bar");
+    /// ```
+    #[track_caller]
+    fn debug_string(self) -> Spec<'a, String, R>;
+}
+
 /// Assert a type formatted into a display string.
 ///
 /// The subject's type must implement `Display` and the expected type must
@@ -2409,6 +2450,57 @@ pub trait AssertHasDisplayString<E> {
     fn does_not_have_display_string(self, expected: E) -> Self;
 }
 
+/// Mapping the subject into its display string representation to do assertions
+/// on its display string.
+///
+/// # Examples
+///
+/// ```
+/// use core::fmt::{self, Display};
+/// use asserting::prelude::*;
+///
+/// struct Foo {
+///     hello: String,
+/// }
+///
+/// impl Display for Foo {fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+///         write!(f, "Hello, {}", self.hello)
+///     }
+/// }
+///
+/// let subject = Foo { hello: "World".into() };
+///
+/// assert_that!(&subject).display_string().is_equal_to("Hello, World");
+/// assert_that!(&subject).display_string().does_not_end_with('!');
+/// ```
+pub trait AssertDisplayString<'a, R> {
+    /// Maps the subject into its display string representation to do assertions
+    /// on its display string.
+    ///
+    /// # Examples
+    ///
+    /// ```
+    /// use core::fmt::{self, Display};
+    /// use asserting::prelude::*;
+    ///
+    /// struct Foo {
+    ///     hello: String,
+    /// }
+    ///
+    /// impl Display for Foo {fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+    ///         write!(f, "Hello, {}", self.hello)
+    ///     }
+    /// }
+    ///
+    /// let subject = Foo { hello: "World".into() };
+    ///
+    /// assert_that!(&subject).display_string().is_equal_to("Hello, World");
+    /// assert_that!(&subject).display_string().does_not_end_with('!');
+    /// ```
+    #[track_caller]
+    fn display_string(self) -> Spec<'a, String, R>;
+}
+
 /// Assert that a string contains a substring or character.
 ///
 /// # Examples
diff --git a/src/error/tests.rs b/src/error/tests.rs
index c7670ce..8701454 100644
--- a/src/error/tests.rs
+++ b/src/error/tests.rs
@@ -359,3 +359,70 @@ mod colored {
         );
     }
 }
+
+#[cfg(feature = "regex")]
+mod with_regex {
+    use super::*;
+
+    #[test]
+    fn error_has_debug_string_matching_regex() {
+        let error = SuperError {
+            source: SourceError::Bar,
+        };
+
+        assert_that(error).debug_string().matches(r"SuperError.*");
+    }
+
+    #[test]
+    fn verify_error_has_debug_string_matching_regex_fails() {
+        let error = SuperError {
+            source: SourceError::Bar,
+        };
+
+        let failures = verify_that(error)
+            .debug_string()
+            .matches(r"SuperError \{ (source|target): Foo \}")
+            .display_failures();
+
+        assert_eq!(
+            failures,
+            &[
+                r"expected subject's debug string to match the regex SuperError \{ (source|target): Foo \}
+               but was: SuperError { source: Bar }
+  does not match regex: SuperError \{ (source|target): Foo \}
+"
+            ]
+        );
+    }
+
+    #[test]
+    fn error_has_display_string_matching_regex() {
+        let error = SuperError {
+            source: SourceError::Bar,
+        };
+
+        assert_that(error).display_string().matches(r".*-error .*");
+    }
+
+    #[test]
+    fn verify_error_has_display_string_matching_regex_fails() {
+        let error = SuperError {
+            source: SourceError::Bar,
+        };
+
+        let failures = verify_that(error)
+            .display_string()
+            .matches(r".*-error-caused.*")
+            .display_failures();
+
+        assert_eq!(
+            failures,
+            &[
+                r"expected subject's display string to match the regex .*-error-caused.*
+               but was: super-error caused by bar error
+  does not match regex: .*-error-caused.*
+"
+            ]
+        );
+    }
+}
diff --git a/src/lib.rs b/src/lib.rs
index 99fe25c..08b3027 100644
--- a/src/lib.rs
+++ b/src/lib.rs
@@ -839,6 +839,7 @@ mod integer;
 mod iterator;
 mod length;
 mod map;
+mod mapping;
 #[cfg(feature = "num-bigint")]
 mod num_bigint;
 mod number;
diff --git a/src/mapping.rs b/src/mapping.rs
new file mode 100644
index 0000000..b8283d1
--- /dev/null
+++ b/src/mapping.rs
@@ -0,0 +1,29 @@
+use crate::assertions::{AssertDebugString, AssertDisplayString};
+use crate::spec::{FailingStrategy, Spec};
+use crate::std::fmt::{Debug, Display};
+use crate::std::format;
+use crate::std::string::{String, ToString};
+
+impl<'a, S, R> AssertDebugString<'a, R> for Spec<'a, S, R>
+where
+    S: Debug,
+    R: FailingStrategy,
+{
+    fn debug_string(self) -> Spec<'a, String, R> {
+        let expression_debug_string = format!("{}'s debug string", self.expression());
+        self.mapping(|subject| format!("{subject:?}"))
+            .named(expression_debug_string)
+    }
+}
+
+impl<'a, S, R> AssertDisplayString<'a, R> for Spec<'a, S, R>
+where
+    S: Display,
+    R: FailingStrategy,
+{
+    fn display_string(self) -> Spec<'a, String, R> {
+        let expression_display_string = format!("{}'s display string", self.expression());
+        self.mapping(|subject| subject.to_string())
+            .named(expression_display_string)
+    }
+}