Outlook emojis: How to insert smileys in Microsoft Outlook

Microsoft Outlook 2021 offers an extremely extensive range of emojis thanks to the support for Unicode. Currently, this extends to Unicode version 12.0 of 2019, which means that only the most recently released copies of 2020 and 2021 are not present. You can see a complete list of all emoji versions on Unicode’s site.

Outlook smileys can be integrated into your email in three ways:

Option 1: By typing out common emoticons

If you are a bit familiar with smiley emoticons, you can simply type one of the known character combinations, and Outlook will automatically replace it with a modern, colorful smiley image. The Microsoft software simply uses the “AutoCorrect” function for this purpose, in which corresponding replacement mechanisms are defined. If you enter the characters :) anywhere in your message, the smiling emoji will automatically appear in Outlook:

Even if there is no equivalent for an emoji according to Outlook’s AutoCorrect feature, you can still use the character sequence, but you must be aware that the recipient will only see the character sequence.

Option 2: Insert emojis using the “Symbol” function

If you are less familiar with emojis and therefore don’t know the usual character combinations, you can alternatively include the Outlook smileys as symbols in your emails. This is how to proceed:

Step 1: First switch to the “Insert” tab and look for the “Symbols” entry in the menu bar. Then click on the “Symbol” button and then on “More symbols” to open the menu of the same name.

Step 2: Now select “Segoe UI Emoji” as the desired font and switch to the subset “Extended Characters – Code Area 1” to go directly to the numerous emoji symbols that the font offers.

Step 3: If you scroll down a bit, you will find a list of the available emojis, which are still displayed in black and white at this point. However, as soon as you add one of these Outlook emojis to your message, it will change into the colored version. To do this, select the desired Outlook emoticon and press “Insert”.

Option 3: Insert emojis via self-defined short code

You can also combine the possibilities of the AutoCorrect feature mentioned in step 1 and the symbol method introduced in option 2 in order to include smileys in your Outlook mails via short code. You can replace predefined short codes with your own or create completely new ones:

Step 1: First open the “Symbol” menu (“Insert” > “Symbol” > “Other symbols”) as described in the previous instructions and select the Outlook smiley that you want to create a keyboard shortcut for.

Step 2: Then click on the “AutoCorrect” button and enter the desired short code in the “Replace” field. Here in the example “1234” is used, but letters or special characters are also possible. For example, set the ever-familiar LOL as the Outlook emoji shortcut with tears of joy.

Step 3: Save the desired shortcode by pressing “Add” (or “Replace” when changing a shortcode) and finally “OK”.

If you are not satisfied with the selection or appearance of the available Outlook smileys, you can also import smileys published by other users or created by you and use them in your emails.

Outlook 2016 provides an interface to Bing that allows you to search for any online images indexed by the search engine. To use the implemented Bing search, proceed as follows:

Step 1: Go to the “Insert” tab in the first step and click on “Pictures” then “Online Pictures”. A new window will open.

Step 2: Now enter “Smiley” in the search bar and start your search by pressing [Enter]. Make sure that a check mark is placed next to “Creative Commons only”.

Step 3: Then select the desired image by left-clicking on it and import it into your message via “Insert”.

If you want to import custom created smileys to Outlook, then you need to follow a different procedure:

Step 1: In the “Insert” tab, first select the “Pictures” option and then select “This PC”.

Step 2: The “Insert Picture” window will then open. Here, specify the location of your smiley file before embedding it into your email by pressing the “Insert” button.

Using smileys in Outlook 2016 and 2019 works the same way as in Outlook 2021. The only difference that can be noticed is a small change in the “Insert” bar. Thus, in the earlier Outlook versions, the “Pictures” and “Online Pictures” options are displayed at the same time. You select the former to insert your own graphics. The latter, if you want to go to the Bing image search.

As a user of the Outlook web app, you can also use smileys in your emails. Unlike the desktop versions, however, the app offers neither an “Icon” nor an “AutoCorrect” function so you can’t create your own shortcodes in Outlook on the web. Nevertheless, the web application also offers various options for inserting emoji into an Outlook mail.

Option 1: Insert classic smiley emoticons

Step 1: Outlook on the web also allows you to enter emoticons, some of which the web application automatically converts into corresponding emojis despite the lack of a correction function. As soon as you type in a colon, you will also be presented with a small selection of possible Outlook smileys.

Step 2: Select the smiley you want or click the three-dot button to open a large list of all available Outlook emojis. Alternatively, you can access them by selecting the smiley at the very bottom.

Option 2: Insert emojis as symbols

Another way to insert smileys in the Outlook web app is to import images, just like in the normal variant. The Bing image search does not exist in the web app, but you can easily embed your own graphics in your mail.

Step 1: Click the small “picture” symbol next to the smiley at the very bottom. This is the “Insert images inline” option.

Step 2: A new window will now open. Browse for the image file you want to insert in your email. After you’ve made your selection, click on “Open”.

Step 3: Your inserted smiley may now need to be resized. To do this, drag the edges or corners of the image until it has the desired size.

If you use the Outlook mobile app for iOS or Android, then inserting smileys and other emojis is even easier than on the other platforms. This is because when composing an email, all you need to do is tap on the smiley icon below your mobile keyboard and then select your desired emoji.