Outlook emojis: How to insert smileys in Microsoft Outlook

There are several options to decorate your Outlook mails with emojis, which include smileys used all over the world. For example, certain emojis can be automatically added thanks to the Outlook’s autocorrect. Otherwise, they can be added from the symbol list or via image import. In the Outlook mobile app, on the other hand, you can access the extensive emoji palette via the smiley icon below your smartphone keyboard.

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Using emojis in Outlook: What are the possibilities?

Originally, emojis were simply represented by ASCII characters, which is why they can be used in all message formats – and therefore also in emails. Characteristic for the smiley type of emoji is that they are constructed from punctuation marks:. A laughing smiley results from the combination :-), while a sad facial expression is represented by the combination :-(. Outlook automatically replaces some of these smileys (known as emoticons) with matching pictograms (graphical representations) when you write, turning them into what people know as emojis.

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Obviously, you can use other smileys in Outlook than just the two mentioned above. To do this, simply include the relevant sequence of characters in your message. Alternatively, you can add the desired smileys to your emails using individually defined character combinations (letters, numbers, special characters).

In addition, Outlook allows you to insert various emojis via the “Symbols” function – including numerous very specific smileys. Those who use Outlook 2016 and Windows 8.1 onwards will even have the colorful emoji versions similar to those present on various social media platforms available to use. You also have the possibility to add emojis to Outlook, which can be found via the Bing image search and implemented via the corresponding function.


Vector-based, colorful emojis can only be displayed with Windows operating systems 8.1 or higher (only partially supported) and Microsoft Outlook 2016, since the Segoe UI Emoji font required for this is only implemented in these versions. The new emoji generation has been fully supported since Windows 10 thanks to the support from Unicode 9.0. If the recipient does not meet the aforementioned requirements, only the simple black and white counterparts of the more elaborately designed emoji will be displayed instead.

Tutorial: How to insert emojis into Outlook

As the previous section stated, there are different variants for using Outlook emojis. How the options work depends on which version of the email client is being used – the revised fonts and emoji models especially play a decisive role. This tutorial will explain how to use emoticons in Outlook 2021, Outlook 2019, and Outlook 2016, as well as in the Outlook on the Web (formerly OWA) and Outlook Mobile apps.


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How to use emojis in Outlook 2021

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”.

Step 4: Now when you type the saved shortcode in an email and then press the space bar, the corresponding smiley will automatically appear.


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How to import your own smileys into Outlook 2021

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.


Smileys that you have imported into Outlook using the “Online Pictures” function still work like image files in emails. In terms of size and arrangement, they do not automatically adapt to the text, as is the case with the standard integrated Outlook smileys. Therefore, you must manually adjust the dimensions and position.

How to use smileys in Outlook 2016 and 2019

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.


You want to print an Outlook email? We will give you tips on how to print emails quickly and easily in Microsoft Outlook and set up icons for quick printing. We have also summarized the most common Outlook shortcuts for you in an overview article.

How to use smileys in Outlook on the web

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.


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How to use smileys in the Outlook mobile app

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.

You can also tap the paperclip icon and insert a smiley as a photo file in your mail. However, unlike the other Outlook platforms, it is not possible to adjust the size of the inserted smiley in the smartphone app.

Conclusion: Smileys improve our email communication

It’s hard to imagine our everyday lives without digital exchange. In private life, many people use Facebook and WhatsApp to quickly send messages to their friends, and communication with business contacts now largely takes place via email, which is also often used privately. However, electronic messages, which are usually sent and received using clients such as Outlook, are anything but perfect. Not only can the Outlook spell checker sometimes malfunctio, there is also a risk that the recipient will misunderstand or misinterpret the tone and context. This is especially true for emails that deal with emotional topics: after all, feelings are sometimes difficult to put into words. The fact that you can't make feelings or irony clear through facial expressions and gestures makes things even more complicated.

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And this is where smileys come into play. These character strings or pictograms, which represent a wide variety of facial expressions, offer the perfect way to portray emotions in text messages and prevent any potential misunderstandings. And striving for comprehensibility is known to be one of the most important parts of email etiquette.


Smileys can also be used when registering emoji domains. Here, a so-called punycode is used — an encoding method that converts Unicode characters into ASCII characters.

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