diff --git a/changelog.d/568.change.rst b/changelog.d/568.change.rst
new file mode 100644
index 000000000..320491019
--- /dev/null
+++ b/changelog.d/568.change.rst
@@ -0,0 +1,2 @@
+The value passed to ``@attr.ib(repr=…)`` can now be either a boolean (as before) or a callable.
+That callable must return a string and is then used for formatting the attribute by the generated ``__repr__()`` method.
diff --git a/docs/examples.rst b/docs/examples.rst
index fad5c2637..5ee63a1bd 100644
--- a/docs/examples.rst
+++ b/docs/examples.rst
@@ -656,7 +656,7 @@ It will get called at the end of the generated ``__init__`` method.
    >>> obj
    C(x=1, y=2, z=3)
 
-Finally, you can exclude single attributes from certain methods:
+You can exclude single attributes from certain methods:
 
 .. doctest::
 
@@ -666,3 +666,14 @@ Finally, you can exclude single attributes from certain methods:
    ...     password = attr.ib(repr=False)
    >>> C("me", "s3kr3t")
    C(user='me')
+
+Alternatively, to influence how the generated ``__repr__()`` method formats a specific attribute, specify a custom callable to be used instead of the ``repr()`` built-in function:
+
+.. doctest::
+
+   >>> @attr.s
+   ... class C(object):
+   ...     user = attr.ib()
+   ...     password = attr.ib(repr=lambda value: '***')
+   >>> C("me", "s3kr3t")
+   C(user='me', password=***)
diff --git a/src/attr/__init__.pyi b/src/attr/__init__.pyi
index 5ffa6dfe5..e331ea62e 100644
--- a/src/attr/__init__.pyi
+++ b/src/attr/__init__.pyi
@@ -26,6 +26,8 @@ _C = TypeVar("_C", bound=type)
 _ValidatorType = Callable[[Any, Attribute[_T], _T], Any]
 _ConverterType = Callable[[Any], _T]
 _FilterType = Callable[[Attribute[_T], _T], bool]
+_ReprType = Callable[[Any], str]
+_ReprArgType = Union[bool, _ReprType]
 # FIXME: in reality, if multiple validators are passed they must be in a list or tuple,
 # but those are invariant and so would prevent subtypes of _ValidatorType from working
 # when passed in a list or tuple.
@@ -49,7 +51,7 @@ class Attribute(Generic[_T]):
     name: str
     default: Optional[_T]
     validator: Optional[_ValidatorType[_T]]
-    repr: bool
+    repr: _ReprArgType
     cmp: bool
     hash: Optional[bool]
     init: bool
@@ -89,7 +91,7 @@ class Attribute(Generic[_T]):
 def attrib(
     default: None = ...,
     validator: None = ...,
-    repr: bool = ...,
+    repr: _ReprArgType = ...,
     cmp: bool = ...,
     hash: Optional[bool] = ...,
     init: bool = ...,
@@ -105,7 +107,7 @@ def attrib(
 def attrib(
     default: None = ...,
     validator: Optional[_ValidatorArgType[_T]] = ...,
-    repr: bool = ...,
+    repr: _ReprArgType = ...,
     cmp: bool = ...,
     hash: Optional[bool] = ...,
     init: bool = ...,
@@ -121,7 +123,7 @@ def attrib(
 def attrib(
     default: _T,
     validator: Optional[_ValidatorArgType[_T]] = ...,
-    repr: bool = ...,
+    repr: _ReprArgType = ...,
     cmp: bool = ...,
     hash: Optional[bool] = ...,
     init: bool = ...,
@@ -137,7 +139,7 @@ def attrib(
 def attrib(
     default: Optional[_T] = ...,
     validator: Optional[_ValidatorArgType[_T]] = ...,
-    repr: bool = ...,
+    repr: _ReprArgType = ...,
     cmp: bool = ...,
     hash: Optional[bool] = ...,
     init: bool = ...,
diff --git a/src/attr/_make.py b/src/attr/_make.py
index bca6f9a90..687b0f447 100644
--- a/src/attr/_make.py
+++ b/src/attr/_make.py
@@ -128,8 +128,14 @@ def attrib(
 
     :type validator: ``callable`` or a ``list`` of ``callable``\\ s.
 
-    :param bool repr: Include this attribute in the generated ``__repr__``
-        method.
+    :param repr: Include this attribute in the generated ``__repr__``
+        method. If ``True``, include the attribute; if ``False``, omit it. By
+        default, the built-in ``repr()`` function is used. To override how the
+        attribute value is formatted, pass a ``callable`` that takes a single
+        value and returns a string. Note that the resulting string is used
+        as-is, i.e. it will be used directly *instead* of calling ``repr()``
+        (the default).
+    :type repr: a ``bool`` or a ``callable`` to use a custom function.
     :param bool cmp: Include this attribute in the generated comparison methods
         (``__eq__`` et al).
     :param hash: Include this attribute in the generated ``__hash__``
@@ -175,6 +181,7 @@ def attrib(
        ``factory=f`` is syntactic sugar for ``default=attr.Factory(f)``.
     .. versionadded:: 18.2.0 *kw_only*
     .. versionchanged:: 19.2.0 *convert* keyword argument removed
+    .. versionchanged:: 19.2.0 *repr* also accepts a custom callable.
     """
     if hash is not None and hash is not True and hash is not False:
         raise TypeError(
@@ -1210,9 +1217,17 @@ def _add_cmp(cls, attrs=None):
 
 def _make_repr(attrs, ns):
     """
-    Make a repr method for *attr_names* adding *ns* to the full name.
+    Make a repr method that includes relevant *attrs*, adding *ns* to the full
+    name.
     """
-    attr_names = tuple(a.name for a in attrs if a.repr)
+
+    # Figure out which attributes to include, and which function to use to
+    # format them. The a.repr value can be either bool or a custom callable.
+    attr_names_with_reprs = tuple(
+        (a.name, repr if a.repr is True else a.repr)
+        for a in attrs
+        if a.repr is not False
+    )
 
     def __repr__(self):
         """
@@ -1244,12 +1259,14 @@ def __repr__(self):
         try:
             result = [class_name, "("]
             first = True
-            for name in attr_names:
+            for name, attr_repr in attr_names_with_reprs:
                 if first:
                     first = False
                 else:
                     result.append(", ")
-                result.extend((name, "=", repr(getattr(self, name, NOTHING))))
+                result.extend(
+                    (name, "=", attr_repr(getattr(self, name, NOTHING)))
+                )
             return "".join(result) + ")"
         finally:
             working_set.remove(id(self))
diff --git a/tests/test_dunders.py b/tests/test_dunders.py
index 69f91a84e..84e092b4f 100644
--- a/tests/test_dunders.py
+++ b/tests/test_dunders.py
@@ -227,6 +227,21 @@ def test_repr_works(self, cls):
         """
         assert "C(a=1, b=2)" == repr(cls(1, 2))
 
+    def test_custom_repr_works(self):
+        """
+        repr returns a sensible value for attributes with a custom repr
+        callable.
+        """
+
+        def custom_repr(value):
+            return "foo:" + str(value)
+
+        @attr.s
+        class C(object):
+            a = attr.ib(repr=custom_repr)
+
+        assert "C(a=foo:1)" == repr(C(1))
+
     def test_infinite_recursion(self):
         """
         In the presence of a cyclic graph, repr will emit an ellipsis and not
diff --git a/tests/typing_example.py b/tests/typing_example.py
index 18e837e52..fb3cddf11 100644
--- a/tests/typing_example.py
+++ b/tests/typing_example.py
@@ -151,3 +151,12 @@ class Validated:
             attr.validators.instance_of(C), attr.validators.instance_of(D)
         ),
     )
+
+
+# Custom repr()
+@attr.s
+class WithCustomRepr:
+    a = attr.ib(repr=True)
+    b = attr.ib(repr=False)
+    c = attr.ib(repr=lambda value: "c is for cookie")
+    d = attr.ib(repr=str)