diff --git a/django/forms/boundfield.py b/django/forms/boundfield.py
index e0ee6b4e78..1b5cbfc47c 100644
--- a/django/forms/boundfield.py
+++ b/django/forms/boundfield.py
@@ -134,18 +134,7 @@ class BoundField(object):
         the form is not bound or the data otherwise.
         """
         if not self.form.is_bound:
-            data = self.form.initial.get(self.name, self.field.initial)
-            if callable(data):
-                if self._initial_value is not UNSET:
-                    data = self._initial_value
-                else:
-                    data = data()
-                    # If this is an auto-generated default date, nix the
-                    # microseconds for standardized handling. See #22502.
-                    if (isinstance(data, (datetime.datetime, datetime.time)) and
-                            not self.field.widget.supports_microseconds):
-                        data = data.replace(microsecond=0)
-                    self._initial_value = data
+            data = self.initial
         else:
             data = self.field.bound_data(
                 self.data, self.form.initial.get(self.name, self.field.initial)
@@ -231,11 +220,27 @@ class BoundField(object):
         id_ = widget.attrs.get('id') or self.auto_id
         return widget.id_for_label(id_)
 
+    @property
+    def initial(self):
+        data = self.form.initial.get(self.name, self.field.initial)
+        if callable(data):
+            if self._initial_value is not UNSET:
+                data = self._initial_value
+            else:
+                data = data()
+                # If this is an auto-generated default date, nix the
+                # microseconds for standardized handling. See #22502.
+                if (isinstance(data, (datetime.datetime, datetime.time)) and
+                        not self.field.widget.supports_microseconds):
+                    data = data.replace(microsecond=0)
+                self._initial_value = data
+        return data
+
     def build_widget_attrs(self, attrs, widget=None):
         if not widget:
             widget = self.field.widget
         attrs = dict(attrs)  # Copy attrs to avoid modifying the argument.
-        if not widget.is_hidden and self.field.required and self.form.use_required_attribute:
+        if widget.use_required_attribute(self.initial) and self.field.required and self.form.use_required_attribute:
             attrs['required'] = True
         if self.field.disabled:
             attrs['disabled'] = True
diff --git a/django/forms/widgets.py b/django/forms/widgets.py
index 13d22672bf..d6b84c10ab 100644
--- a/django/forms/widgets.py
+++ b/django/forms/widgets.py
@@ -248,6 +248,9 @@ class Widget(six.with_metaclass(RenameWidgetMethods)):
         """
         return id_
 
+    def use_required_attribute(self, initial):
+        return not self.is_hidden
+
 
 class Input(Widget):
     """
@@ -429,6 +432,9 @@ class ClearableFileInput(FileInput):
             return False
         return upload
 
+    def use_required_attribute(self, initial):
+        return super(ClearableFileInput, self).use_required_attribute(initial) and not initial
+
 
 class Textarea(Widget):
     def __init__(self, attrs=None):
@@ -795,12 +801,10 @@ class CheckboxSelectMultiple(RendererMixin, SelectMultiple):
     renderer = CheckboxFieldRenderer
     _empty_value = []
 
-    def build_attrs(self, extra_attrs=None, **kwargs):
-        attrs = super(CheckboxSelectMultiple, self).build_attrs(extra_attrs, **kwargs)
-        # Remove the 'required' attribute because browser validation would
+    def use_required_attribute(self, initial):
+        # Don't use the 'required' attribute because browser validation would
         # require all checkboxes to be checked instead of at least one.
-        attrs.pop('required', None)
-        return attrs
+        return False
 
 
 class MultiWidget(Widget):
diff --git a/docs/releases/1.10.1.txt b/docs/releases/1.10.1.txt
index 2ebd36cf0f..b834915701 100644
--- a/docs/releases/1.10.1.txt
+++ b/docs/releases/1.10.1.txt
@@ -45,3 +45,6 @@ Bugfixes
 
 * Fixed crash of ``django.views.static.serve()`` with ``show_indexes`` enabled
   (:ticket:`26973`).
+
+* Fixed ``ClearableFileInput`` to avoid the ``required`` HTML attribute when
+  initial data exists (:ticket:`27037`).
diff --git a/tests/forms_tests/tests/test_forms.py b/tests/forms_tests/tests/test_forms.py
index 773b89a7bc..0e0ea9f1c2 100644
--- a/tests/forms_tests/tests/test_forms.py
+++ b/tests/forms_tests/tests/test_forms.py
@@ -2360,6 +2360,15 @@ Password: <input type="password" name="password" required />
             '<tr><th>File1:</th><td><input type="file" name="file1" required /></td></tr>',
         )
 
+        # A required file field with initial data should not contain the
+        # required HTML attribute. The file input is left blank by the user to
+        # keep the existing, initial value.
+        f = FileForm(initial={'file1': 'resume.txt'}, auto_id=False)
+        self.assertHTMLEqual(
+            f.as_table(),
+            '<tr><th>File1:</th><td><input type="file" name="file1" /></td></tr>',
+        )
+
     def test_basic_processing_in_view(self):
         class UserRegistration(Form):
             username = CharField(max_length=10)
diff --git a/tests/forms_tests/widget_tests/test_checkboxselectmultiple.py b/tests/forms_tests/widget_tests/test_checkboxselectmultiple.py
index 10d025e4c2..2d73f2b589 100644
--- a/tests/forms_tests/widget_tests/test_checkboxselectmultiple.py
+++ b/tests/forms_tests/widget_tests/test_checkboxselectmultiple.py
@@ -112,3 +112,11 @@ class CheckboxSelectMultipleTest(WidgetTest):
         </ul>
         """
         self.check_html(widget, 'letters', ['a', 'c'], html=html)
+
+    def test_use_required_attribute(self):
+        widget = self.widget(choices=self.beatles)
+        # Always False because browser validation would require all checkboxes
+        # to be checked instead of at least one.
+        self.assertIs(widget.use_required_attribute(None), False)
+        self.assertIs(widget.use_required_attribute([]), False)
+        self.assertIs(widget.use_required_attribute(['J', 'P']), False)
diff --git a/tests/forms_tests/widget_tests/test_clearablefileinput.py b/tests/forms_tests/widget_tests/test_clearablefileinput.py
index 720f17b035..3727d0c0df 100644
--- a/tests/forms_tests/widget_tests/test_clearablefileinput.py
+++ b/tests/forms_tests/widget_tests/test_clearablefileinput.py
@@ -143,3 +143,9 @@ class ClearableFileInputTest(WidgetTest):
 
         html = self.widget.render('myfile', NoURLFieldFile())
         self.assertHTMLEqual(html, '<input name="myfile" type="file" />')
+
+    def test_use_required_attribute(self):
+        # False when initial data exists. The file input is left blank by the
+        # user to keep the existing, initial value.
+        self.assertIs(self.widget.use_required_attribute(None), True)
+        self.assertIs(self.widget.use_required_attribute('resume.txt'), False)
diff --git a/tests/forms_tests/widget_tests/test_hiddeninput.py b/tests/forms_tests/widget_tests/test_hiddeninput.py
index 039e89d5cc..d1604a31e4 100644
--- a/tests/forms_tests/widget_tests/test_hiddeninput.py
+++ b/tests/forms_tests/widget_tests/test_hiddeninput.py
@@ -8,3 +8,10 @@ class HiddenInputTest(WidgetTest):
 
     def test_render(self):
         self.check_html(self.widget, 'email', '', html='<input type="hidden" name="email" />')
+
+    def test_use_required_attribute(self):
+        # Always False to avoid browser validation on inputs hidden from the
+        # user.
+        self.assertIs(self.widget.use_required_attribute(None), False)
+        self.assertIs(self.widget.use_required_attribute(''), False)
+        self.assertIs(self.widget.use_required_attribute('foo'), False)
diff --git a/tests/forms_tests/widget_tests/test_textinput.py b/tests/forms_tests/widget_tests/test_textinput.py
index 33e455a160..65b5da4e03 100644
--- a/tests/forms_tests/widget_tests/test_textinput.py
+++ b/tests/forms_tests/widget_tests/test_textinput.py
@@ -76,3 +76,9 @@ class TextInputTest(WidgetTest):
     def test_attrs_safestring(self):
         widget = TextInput(attrs={'onBlur': mark_safe("function('foo')")})
         self.check_html(widget, 'email', '', html='<input onBlur="function(\'foo\')" type="text" name="email" />')
+
+    def test_use_required_attribute(self):
+        # Text inputs can safely trigger the browser validation.
+        self.assertIs(self.widget.use_required_attribute(None), True)
+        self.assertIs(self.widget.use_required_attribute(''), True)
+        self.assertIs(self.widget.use_required_attribute('resume.txt'), True)