diff --git a/examples/checkable-item.php b/examples/checkable-item.php
new file mode 100644
index 00000000..13fdde04
--- /dev/null
+++ b/examples/checkable-item.php
@@ -0,0 +1,41 @@
+<?php
+
+use PhpSchool\CliMenu\CliMenu;
+use PhpSchool\CliMenu\Builder\CliMenuBuilder;
+use PhpSchool\CliMenu\MenuItem\CheckableItem;
+
+require_once(__DIR__ . '/../vendor/autoload.php');
+
+$itemCallable = function (CliMenu $menu) {
+    /** @var CheckableItem $item */
+    $item = $menu->getSelectedItem();
+
+    $item->toggle();
+
+    $menu->redraw();
+};
+
+$menu = (new CliMenuBuilder)
+    ->setTitle('Select a Language')
+    ->addSubMenu('Compiled', function (CliMenuBuilder $b) use ($itemCallable) {
+        $b->setTitle('Compiled Languages')
+            ->addCheckableItem('Rust', $itemCallable)
+            ->addCheckableItem('C++', $itemCallable)
+            ->addCheckableItem('Go', $itemCallable)
+            ->addCheckableItem('Java', $itemCallable)
+            ->addCheckableItem('C', $itemCallable)
+        ;
+    })
+    ->addSubMenu('Interpreted', function (CliMenuBuilder $b) use ($itemCallable) {
+        $b->setTitle('Interpreted Languages')
+            ->setUncheckedMarker('[○] ')
+            ->setCheckedMarker('[●] ')
+            ->addCheckableItem('PHP', $itemCallable)
+            ->addCheckableItem('Javascript', $itemCallable)
+            ->addCheckableItem('Ruby', $itemCallable)
+            ->addCheckableItem('Python', $itemCallable)
+        ;
+    })
+    ->build();
+
+$menu->open();
diff --git a/src/Builder/CliMenuBuilder.php b/src/Builder/CliMenuBuilder.php
index af9668a6..7bd4188d 100644
--- a/src/Builder/CliMenuBuilder.php
+++ b/src/Builder/CliMenuBuilder.php
@@ -6,6 +6,7 @@
 use PhpSchool\CliMenu\Action\GoBackAction;
 use PhpSchool\CliMenu\Exception\InvalidShortcutException;
 use PhpSchool\CliMenu\MenuItem\AsciiArtItem;
+use PhpSchool\CliMenu\MenuItem\CheckableItem;
 use PhpSchool\CliMenu\MenuItem\LineBreakItem;
 use PhpSchool\CliMenu\MenuItem\MenuItemInterface;
 use PhpSchool\CliMenu\MenuItem\MenuMenuItem;
@@ -130,6 +131,17 @@ public function addItems(array $items) : self
         return $this;
     }
 
+    public function addCheckableItem(
+        string $text,
+        callable $itemCallable,
+        bool $showItemExtra = false,
+        bool $disabled = false
+    ) : self {
+        $this->addMenuItem(new CheckableItem($text, $itemCallable, $showItemExtra, $disabled));
+
+        return $this;
+    }
+
     public function addStaticItem(string $text) : self
     {
         $this->addMenuItem(new StaticItem($text));
@@ -395,6 +407,20 @@ public function setSelectedMarker(string $marker) : self
         return $this;
     }
 
+    public function setUncheckedMarker(string $marker) : self
+    {
+        $this->style->setUncheckedMarker($marker);
+
+        return $this;
+    }
+
+    public function setCheckedMarker(string $marker) : self
+    {
+        $this->style->setCheckedMarker($marker);
+
+        return $this;
+    }
+
     public function setItemExtra(string $extra) : self
     {
         $this->style->setItemExtra($extra);
diff --git a/src/MenuItem/CheckableItem.php b/src/MenuItem/CheckableItem.php
new file mode 100644
index 00000000..93f021d7
--- /dev/null
+++ b/src/MenuItem/CheckableItem.php
@@ -0,0 +1,166 @@
+<?php
+
+namespace PhpSchool\CliMenu\MenuItem;
+
+use PhpSchool\CliMenu\MenuItem;
+use PhpSchool\CliMenu\MenuStyle;
+use PhpSchool\CliMenu\Util\StringUtil;
+
+class CheckableItem implements MenuItem\MenuItemInterface
+{
+    /**
+     * @var callable
+     */
+    private $selectAction;
+
+    /**
+     * @var string
+     */
+    private $text = '';
+
+    /**
+     * @var bool
+     */
+    private $showItemExtra = false;
+
+    /**
+     * @var bool
+     */
+    private $disabled = false;
+
+    /**
+     * @var bool
+     */
+    private $checked = false;
+
+    public function __construct(
+        string $text,
+        callable $selectAction,
+        bool $showItemExtra = false,
+        bool $disabled = false
+    ) {
+        $this->text          = $text;
+        $this->selectAction  = $selectAction;
+        $this->showItemExtra = $showItemExtra;
+        $this->disabled      = $disabled;
+    }
+
+    /**
+     * Execute the items callable if required
+     */
+    public function getSelectAction() : ?callable
+    {
+        return $this->selectAction;
+    }
+
+    /**
+     * Return the raw string of text
+     */
+    public function getText() : string
+    {
+        return $this->text;
+    }
+
+    /**
+     * Set the raw string of text
+     */
+    public function setText(string $text) : void
+    {
+        $this->text = $text;
+    }
+
+    /**
+     * The output text for the item
+     *
+     * @param MenuStyle $style
+     * @param bool $selected Currently unused in this class
+     * @return array
+     */
+    public function getRows(MenuStyle $style, bool $selected = false) : array
+    {
+        $marker = sprintf("%s", $this->checked ? $style->getCheckedMarker() : $style->getUncheckedMarker());
+
+        $length = $style->getDisplaysExtra()
+            ? $style->getContentWidth() - (mb_strlen($style->getItemExtra()) + 2)
+            : $style->getContentWidth();
+
+        $rows = explode(
+            "\n",
+            StringUtil::wordwrap(
+                sprintf('%s%s', $marker, $this->text),
+                $length,
+                sprintf("\n%s", str_repeat(' ', mb_strlen($marker)))
+            )
+        );
+
+        return array_map(function ($row, $key) use ($style, $length) {
+            $text = $this->disabled ? $style->getDisabledItemText($row) : $row;
+
+            if ($key === 0) {
+                return $this->showItemExtra
+                    ? sprintf('%s%s  %s', $text, str_repeat(' ', $length - mb_strlen($row)), $style->getItemExtra())
+                    : $text;
+            }
+
+            return $text;
+        }, $rows, array_keys($rows));
+    }
+
+    /**
+     * Can the item be selected
+     */
+    public function canSelect() : bool
+    {
+        return !$this->disabled;
+    }
+
+    public function showsItemExtra() : bool
+    {
+        return $this->showItemExtra;
+    }
+
+    /**
+     * Enable showing item extra
+     */
+    public function showItemExtra() : void
+    {
+        $this->showItemExtra = true;
+    }
+
+    /**
+     * Disable showing item extra
+     */
+    public function hideItemExtra() : void
+    {
+        $this->showItemExtra = false;
+    }
+
+    /**
+     * Toggles checked state
+     */
+    public function toggle()
+    {
+        $this->checked = !$this->checked;
+    }
+
+    /**
+     * Sets checked state to true
+     */
+    public function setChecked()
+    {
+        $this->checked = true;
+    }
+
+    /**
+     * Sets checked state to false
+     */
+    public function setUnchecked()
+    {
+        $this->checked = false;
+    }
+
+    public function getChecked(): bool
+    {
+        return $this->checked;
+    }
+}
diff --git a/src/MenuStyle.php b/src/MenuStyle.php
index a740c40a..eececec9 100644
--- a/src/MenuStyle.php
+++ b/src/MenuStyle.php
@@ -69,6 +69,16 @@ class MenuStyle
      */
     private $unselectedMarker;
 
+    /**
+     * @var string
+     */
+    private $checkedMarker;
+
+    /**
+     * @var string
+     */
+    private $uncheckedMarker;
+
     /**
      * @var string
      */
@@ -158,6 +168,8 @@ class MenuStyle
         'margin' => 2,
         'selectedMarker' => '● ',
         'unselectedMarker' => '○ ',
+        'checkedMarker' => '[✔] ',
+        'uncheckedMarker' => '[ ] ',
         'itemExtra' => '✔',
         'displaysExtra' => false,
         'titleSeparator' => '=',
@@ -229,6 +241,8 @@ public function __construct(Terminal $terminal = null)
         $this->setMargin(self::$defaultStyleValues['margin']);
         $this->setSelectedMarker(self::$defaultStyleValues['selectedMarker']);
         $this->setUnselectedMarker(self::$defaultStyleValues['unselectedMarker']);
+        $this->setCheckedMarker(self::$defaultStyleValues['checkedMarker']);
+        $this->setUncheckedMarker(self::$defaultStyleValues['uncheckedMarker']);
         $this->setItemExtra(self::$defaultStyleValues['itemExtra']);
         $this->setDisplaysExtra(self::$defaultStyleValues['displaysExtra']);
         $this->setTitleSeparator(self::$defaultStyleValues['titleSeparator']);
@@ -250,6 +264,8 @@ public function hasChangedFromDefaults() : bool
             $this->margin,
             $this->selectedMarker,
             $this->unselectedMarker,
+            $this->checkedMarker,
+            $this->uncheckedMarker,
             $this->itemExtra,
             $this->displaysExtra,
             $this->titleSeparator,
@@ -557,6 +573,30 @@ public function getMarker(bool $selected) : string
         return $selected ? $this->selectedMarker : $this->unselectedMarker;
     }
 
+    public function getCheckedMarker() : string
+    {
+        return $this->checkedMarker;
+    }
+
+    public function setCheckedMarker(string $marker) : self
+    {
+        $this->checkedMarker = $marker;
+
+        return $this;
+    }
+
+    public function getUncheckedMarker() : string
+    {
+        return $this->uncheckedMarker;
+    }
+
+    public function setUncheckedMarker(string $marker) : self
+    {
+        $this->uncheckedMarker = $marker;
+
+        return $this;
+    }
+
     public function setItemExtra(string $itemExtra) : self
     {
         $this->itemExtra = $itemExtra;
diff --git a/test/Builder/CliMenuBuilderTest.php b/test/Builder/CliMenuBuilderTest.php
index a57bfae2..70e72c68 100644
--- a/test/Builder/CliMenuBuilderTest.php
+++ b/test/Builder/CliMenuBuilderTest.php
@@ -5,6 +5,7 @@
 use PhpSchool\CliMenu\CliMenu;
 use PhpSchool\CliMenu\Builder\CliMenuBuilder;
 use PhpSchool\CliMenu\MenuItem\AsciiArtItem;
+use PhpSchool\CliMenu\MenuItem\CheckableItem;
 use PhpSchool\CliMenu\MenuItem\LineBreakItem;
 use PhpSchool\CliMenu\MenuItem\MenuMenuItem;
 use PhpSchool\CliMenu\MenuItem\SelectableItem;
@@ -64,6 +65,8 @@ public function testModifyStyles() : void
         $builder->setMargin(4);
         $builder->setUnselectedMarker('>');
         $builder->setSelectedMarker('x');
+        $builder->setUncheckedMarker('-');
+        $builder->setCheckedMarker('+');
         $builder->setItemExtra('*');
         $builder->setTitleSeparator('-');
 
@@ -78,6 +81,8 @@ public function testModifyStyles() : void
         self::assertEquals(4, $style->getMargin());
         self::assertEquals('>', $style->getUnselectedMarker());
         self::assertEquals('x', $style->getSelectedMarker());
+        self::assertEquals('-', $style->getUncheckedMarker());
+        self::assertEquals('+', $style->getCheckedMarker());
         self::assertEquals('*', $style->getItemExtra());
         self::assertEquals('-', $style->getTitleSeparator());
     }
@@ -364,6 +369,31 @@ public function testAddMultipleItems() : void
         $this->checkMenuItems($menu, $expected);
     }
 
+    public function testAddCheckableItem() : void
+    {
+        $callable = function () {
+        };
+
+        $builder = new CliMenuBuilder;
+        $builder->disableDefaultItems();
+        $builder->addCheckableItem('Item 1', $callable);
+        $builder->addCheckableItem('Item 2', $callable);
+        $menu = $builder->build();
+
+        $expected = [
+            [
+                'class' => CheckableItem::class,
+                'text'  => 'Item 1',
+            ],
+            [
+                'class' => CheckableItem::class,
+                'text'  => 'Item 2',
+            ],
+        ];
+
+        $this->checkMenuItems($menu, $expected);
+    }
+
     public function testAddStaticItem() : void
     {
 
diff --git a/test/MenuItem/CheckableItemTest.php b/test/MenuItem/CheckableItemTest.php
new file mode 100644
index 00000000..4b947fb1
--- /dev/null
+++ b/test/MenuItem/CheckableItemTest.php
@@ -0,0 +1,160 @@
+<?php
+
+namespace PhpSchool\CliMenuTest\MenuItem;
+
+use PhpSchool\CliMenu\MenuItem\CheckableItem;
+use PhpSchool\CliMenu\MenuStyle;
+use PhpSchool\Terminal\Terminal;
+use PHPUnit\Framework\TestCase;
+
+class CheckableItemTest extends TestCase
+{
+    public function testCanSelectIsTrue() : void
+    {
+        $item = new CheckableItem('Item', function () {
+        });
+        $this->assertTrue($item->canSelect());
+    }
+
+    public function testGetSelectAction() : void
+    {
+        $callable = function () {
+        };
+        $item = new CheckableItem('Item', $callable);
+        $this->assertSame($callable, $item->getSelectAction());
+    }
+
+    public function testShowsItemExtra() : void
+    {
+        $item = new CheckableItem('Item', function () {
+        });
+        $this->assertFalse($item->showsItemExtra());
+
+        $item = new CheckableItem('Item', function () {
+        }, true);
+        $this->assertTrue($item->showsItemExtra());
+    }
+
+    public function testGetText() : void
+    {
+        $item = new CheckableItem('Item', function () {
+        });
+        $this->assertEquals('Item', $item->getText());
+    }
+
+    public function testGetRows() : void
+    {
+        $terminal = $this->createMock(Terminal::class);
+        $terminal->expects($this->any())->method('getWidth')->willReturn(100);
+
+        $menuStyle = new MenuStyle($terminal);
+        $menuStyle->setPaddingLeftRight(0);
+        $menuStyle->setWidth(8);
+
+        $item = new CheckableItem('Item', function () {
+        });
+
+        $itemChecked = new CheckableItem('Item', function () {
+        });
+        $itemChecked->toggle();
+        $this->assertEquals(['[ ] Item'], $item->getRows($menuStyle));
+        $this->assertEquals(['[ ] Item'], $item->getRows($menuStyle, false));
+        $this->assertEquals(['[✔] Item'], $itemChecked->getRows($menuStyle, true));
+    }
+
+    public function testSetText() : void
+    {
+        $terminal = $this->createMock(Terminal::class);
+        $terminal->expects($this->any())->method('getWidth')->willReturn(100);
+
+        $menuStyle = new MenuStyle($terminal);
+        $menuStyle->setPaddingLeftRight(0);
+        $menuStyle->setWidth(12);
+
+        $item = new CheckableItem('Item', function () {
+        });
+        $item->setText('New Text');
+
+        $itemChecked = new CheckableItem('Item', function () {
+        });
+        $itemChecked->setText('New Text');
+        $itemChecked->toggle();
+        $this->assertEquals(['[ ] New Text'], $item->getRows($menuStyle));
+        $this->assertEquals(['[ ] New Text'], $item->getRows($menuStyle, false));
+        $this->assertEquals(['[✔] New Text'], $itemChecked->getRows($menuStyle, true));
+    }
+
+    public function testTogglesMarker() : void
+    {
+        $terminal = $this->createMock(Terminal::class);
+        $terminal->expects($this->any())->method('getWidth')->willReturn(100);
+
+        $menuStyle = new MenuStyle($terminal);
+        $menuStyle->setPaddingLeftRight(0);
+        $menuStyle->setWidth(12);
+
+        $item = new CheckableItem('Item', function () {
+        });
+
+        $itemChecked = new CheckableItem('Item', function () {
+        });
+        $itemChecked->toggle();
+        $this->assertEquals(['[ ] Item'], $item->getRows($menuStyle));
+        $this->assertEquals(['[ ] Item'], $item->getRows($menuStyle, false));
+        $this->assertEquals(['[✔] Item'], $itemChecked->getRows($menuStyle, true));
+
+        $itemChecked->toggle();
+
+        $this->assertEquals(['[ ] Item'], $itemChecked->getRows($menuStyle, true));
+    }
+
+    public function testGetRowsWithItemExtra() : void
+    {
+        $terminal = $this->createMock(Terminal::class);
+        $terminal->expects($this->any())->method('getWidth')->willReturn(100);
+
+        $menuStyle = new MenuStyle($terminal);
+        $menuStyle->setPaddingLeftRight(0);
+        $menuStyle->setWidth(20);
+        $menuStyle->setItemExtra('[EXTRA]');
+        $menuStyle->setDisplaysExtra(true);
+
+        $item = new CheckableItem('Item', function () {
+        }, true);
+        $this->assertEquals(['[ ] Item     [EXTRA]'], $item->getRows($menuStyle));
+    }
+
+    public function testGetRowsWithMultipleLinesWithItemExtra() : void
+    {
+        $terminal = $this->createMock(Terminal::class);
+        $terminal->expects($this->any())->method('getWidth')->willReturn(100);
+
+        $menuStyle = new MenuStyle($terminal);
+        $menuStyle->setPaddingLeftRight(0);
+        $menuStyle->setWidth(20);
+        $menuStyle->setItemExtra('[EXTRA]');
+        $menuStyle->setDisplaysExtra(true);
+
+        $item = new CheckableItem('LONG ITEM LINE', function () {
+        }, true);
+        $this->assertEquals(
+            [
+                "[ ] LONG     [EXTRA]",
+                "    ITEM LINE",
+            ],
+            $item->getRows($menuStyle)
+        );
+    }
+
+    public function testHideAndShowItemExtra() : void
+    {
+        $item = new CheckableItem('Item', function () {
+        });
+
+        $this->assertFalse($item->showsItemExtra());
+        $item->showItemExtra();
+        $this->assertTrue($item->showsItemExtra());
+        $item->hideItemExtra();
+        $this->assertFalse($item->showsItemExtra());
+    }
+}
diff --git a/test/MenuStyleTest.php b/test/MenuStyleTest.php
index 1c954cc3..6f40fb35 100644
--- a/test/MenuStyleTest.php
+++ b/test/MenuStyleTest.php
@@ -100,6 +100,8 @@ public function testGetterAndSetters() : void
         $style->setFg('yellow');
         $style->setUnselectedMarker('-');
         $style->setSelectedMarker('>');
+        $style->setUncheckedMarker('/');
+        $style->setCheckedMarker('+');
         $style->setItemExtra('EXTRA!');
         $style->setDisplaysExtra(true);
         $style->setTitleSeparator('+');
@@ -117,6 +119,8 @@ public function testGetterAndSetters() : void
         self::assertSame('yellow', $style->getFg());
         self::assertSame('-', $style->getUnselectedMarker());
         self::assertSame('>', $style->getSelectedMarker());
+        self::assertEquals('/', $style->getUncheckedMarker());
+        self::assertEquals('+', $style->getCheckedMarker());
         self::assertSame('EXTRA!', $style->getItemExtra());
         self::assertTrue($style->getDisplaysExtra());
         self::assertSame('+', $style->getTitleSeparator());