Colorful emoticons and smiley faces in Outlook

This is indeed a touchy subject for some core Outlook users but also quite a common request from the more casual Outlook users or home users who are familiar with emoji in other apps and on webpages.

While Outlook 2016 and later does offer full support for full color emoji, how to insert them may not be that obvious and you may want to customize some as well.

Even though Outlook 2013 and previous don’t offer native support for colorful smileys, it is easy to set this up via AutoCorrect. This way, smileys will directly convert from their textual counterpart into an icon of your choice.

In fact, the built-in conversion of :-) to is also done via AutoCorrect.

Outlook 2016, 2019 and as part of Office 365

When you are using Outlook 2016, 2019 or as part of an Office 365 subscription, then Outlook supports over a 1000 colorful emoji when being used on Windows 10 or Windows 8.

When using Outlook on Windows 10, a quick way to insert them is via the Emoji Panel. This panel can be brought up by using one of the following keyboard shortcuts;

• Windows logo key + ;
• Windows logo key + .

Once the Emoji Panel is open, you can either type a description to search for the emoji or browse for the emoji in the panel.

Emoji Panel on Windows 10.

AutoCorrect shortcodes also exist in Outlook for the emoji shown below. In the next section, it is explained how you can create shortcode mappings of your own to quickly insert your favorite emoji, or when you want to use other emoji pictures. Using emoji images of your own can also prevent them from being received in black and white or as empty squares on some Windows 7 computers.

Colorful emoji support in Outlook.

Adding new smileys, icons and logos to AutoCorrect (all Outlook versions)

In the example below I’ve used an emoticon from the Skype webpage.

1. Create a new message.
2. Insert the image or symbol of choice either from disk, the web or from a symbol font such as Wingdings. (See the bottom of this guide for more info on this.)
3. Select the inserted image or symbol.
4. Open the AutoCorrect options dialog;
• Outlook 2007
  Office logo at the top left corner-> Editor Options-> Proofing-> button AutoCorrect Options…
• Outlook 2010 / 2013 / 2016 / 2019 / Office 365
  File-> Options-> Mail-> button: Spelling and Autocorrect…-> button: AutoCorrect Options…
5. Select the AutoCorrect tab.
6. Type your characters that should convert into this image in the “Replace” field.
   For instance :-) or :-P.
7. Verify that the “With” option is set to “Formatted text”. You may not see your image in the box below it (this is a small bug in Outlook).
8. Click the button Add or Replace (in case the entry already exists).
9. In the list below, you’ll now see an entry for your typed characters. The asterisk (*) indicates that it will be replaced with an image.
10. Press OK until you’ve returned to your message.

After you’ve configured the emoticon, the next time that you want to insert it, simply type your emoticon in characters and it will be replaced with your image (you might need to press the Spacebar or ENTER afterwards for it to actually convert).

Via AutoCorrect you can replace Outlook's dull emoticons will colorful new ones and add new ones of your own as well. (Due to a bug in Outlook/Word the image may not always show in the AutoCorrect dialog.)

Note 1: Outlook doesn’t offer support for animated gifs, but if the message is received by a mail client which does, the gif image will still animate. For more info see; Making gifs animate.

Note 2: If AutoCorrect is not available for you see Automatic spell check and Autocorrect not working.

Easy access to AutoCorrect options

When setting up your emoticons, quicker access to the AutoCorrect options dialog might be handy.

For this you can add the AutoCorrect command to the Quick Access Toolbar (QAT).

Adding the AutoCorrect Options button to the QAT can significantly speed up the configuration of custom emoticons.

Backup your AutoCorrect entries

Once you’ve configured your custom emoticons, you might want to create a backup of them. To do this, make a copy of your normalemail.dotm file when Outlook is closed.

You can find the file here;

• C:\Users\%username%\AppData\Roaming\Microsoft\Templates

Note: For more locations and files in which Outlook stores its data and settings see the guide; Files and Settings guide for Outlook.

Source of a new smiley, icon or logo

You can use basically anything as a source for your new emoticon;

• An image from your hard disk.
  Insert-> Picture
• An image copied from a web page.
  To insert an image directly from a webpage, right click on the image, choose Copy and paste it in your message (CTRL+V).
• A symbol from a font such as Wingdings.
  When you inserted a symbol from a font, you can enlarge it and apply a color to it.