Outlook: How to use emojis in Outlook

Digital communication has become an integral part of our everyday lives. Many people use Facebook and WhatsApp to quickly send messages to their friends. E-mails are used for communicating with business contacts although many people also use e-mail often in their private lives. The electronic messages, which are usually sent and received with the help of clients such as Outlook, are anything but perfect. Since e-mails only transmit information in written form, there is a risk that the recipient could misunderstand or misinterpret the tone and context. This is especially the case for e-mails that deal with emotional topics: After all, feelings are sometimes difficult to put into words. The fact that feelings or irony cannot be made clear through facial expressions and gestures makes things even more complicated.

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The simple and practical solution to this problem is to use emojis. The word “emoji” is an umbrella term and refers to images consisting of not just smileys, but also common objects, places, types of weather, and animals. These character strings or pictograms offer the perfect opportunity to represent emotions in text messages. This guide explains the different options available for using emojis in Outlook.

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 e-mails. 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 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 e-mails 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 colourful emoji versions similar to those present on various social media platforms available to them. 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, colourful 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 it being supported by 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 e-mail client is being used – the revised fonts and emoji models especially play a decisive role. This tutorial explains how to use emojis in Outlook 2016 and Outlook 2013, as well as in the web app Outlook on the web (formerly OWA). The differences are also highlighted.

How to use emojis in Outlook 2016

Thanks to the Unicode 9.0 support, Microsoft Outlook 2016 offers an extremely wide range of around 60 different emojis. You can integrate these into your e-mail 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, colourful 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 smileys available in Outlook 2016 as symbols in your e-mails. To do this, first switch to the “Insert” tab and search for the “Symbol” entry in the menu bar. Then click on the “Symbol” button and then on “More Symbols” to open the menu:

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. 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 coloured version. To do this, select the desired emoji 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.

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. Then click on the “AutoCorrect” button and enter the desired short code in the “Replace” field (here in the example “1234,” but letters or special characters are also possible). Save the desired abbreviation by clicking “Replace” and then “OK.

If you now use the saved short code in an e-mail, the corresponding smiley will appear automatically.

How to import your own smileys into Outlook 2016

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 e-mails.

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, go to the “Insert” tab in the first step and click on “Online Pictures.” Then enter “smiley” in the search bar and start the search using the magnifying glass icon. Select the desired image by left-clicking on it and import it into your message via “Insert.”

To import custom smileys into Outlook, select the “Pictures” option in the “Insert” tab. In the menu that opens, enter the location of the smiley file before inserting it into your e-mail by pressing the “Insert” button:


Smileys that you have imported into Outlook using the “Online Pictures” function still work like image files in e-mails. 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 2013

The use of smileys in Outlook 2013 is basically similar to Outlook 2016. The approximately 40 available emojis, which are exclusively black and white, can be integrated in the three ways already mentioned, although there are a few minor differences compared to the successor version:

Option 1: Input of classic smiley emoticons

You can also use smileys in Outlook 2013 by typing in the respective emoticon. However, the number of emoticons that are automatically converted into emojis by the “AutoCorrect” function is comparatively small. Here are the six emoticons than can be converted:

Option 2: Insert emojis as symbols

Like its younger 2016 counterpart, Microsoft Outlook 2013 allows you to include specific characters and symbols, including smiley emojis, in your e-mails using the “Symbol” function. To make use of this option, open the “INSERT” tab when writing the message and select the menu items “Symbol” and “More Symbols…” one after the other:

In the following menu, select the font “Segoe UI Symbol” and the subset “Extended Characters – Plane 1,” whereupon Outlook automatically jumps to the extended character set of this font. Scroll down this list a little to see the smiley emojis available in Outlook 2013. To use these smileys in a message, click on the desired emoji and then press “Insert.

Option 3: Create custom keyboard shortcuts for inserting smileys

If you want to save yourself the trouble of using the “Icon” menu in the long run, just create your own shortcuts to add your favourite Outlook smileys. The first step is to open the menu again (“INSERT” “Symbol” “More Symbols…”). Then select the smiley of your choice and press the AutoCorrect button. In the “Replace:” field, type in the desired short code. Then repeat this step for all smiley emojis that you want to mark with individual shortcuts.

Outlook 2013: How the smiley import works

You can add to the amount of smileys in Outlook 2013 by importing files. However, the files are not converted so that the smileys are embedded as images even after the import. In contrast to the character-based emoticons and emojis, they do not automatically fit into the text image. Therefore, adjustments in height, width, and positioning are sometimes necessary. You can insert the smiley files either from your local hard disk or from the Bing image search, for which a corresponding interface has been implemented.

In both cases, you must open the “INSERT” tab in the first step. Then click “Pictures” to import a locally saved file or “Online Pictures” to use the Bing search:

To import locally saved images, simply specify the file’s location and click “Insert” to finish. Start the web search by entering the term “Smiley” in the field “Search in Bing” and then clicking on the magnifying glass symbol. Then select one or more images and import them via “Insert.

How to use smileys in Outlook on the web

It’s also possible to use smileys in your e-mails on the Outlook Web App. In contrast to the desktop versions, however, the app offers neither a “Symbol” nor an “AutoCorrect” feature - you cannot therefore create your own short codes in Outlook on the web. Nevertheless, the web application also offers various possibilities to use the approximately 40 smiley emojis that are available.

Option 1: Type in smiley emoticons

Of course, you can also enter emoticons into Outlook on the web, which the web application converts in part automatically into corresponding emojis, despite the missing correction function. As you type, the Outlook app even suggests possible emojis or other icons that you can click on to include in your text:

If the suggestions do not meet your expectations, you can of course reject them: To do this, first press the space bar. The e-mail software will then accept the first suggestion, but you can undo this by pressing the backspace key. If you then use the space bar or the enter key again, the emoticon stays the same.

Option 2: Add smileys via the “Emoji” button

In contrast to the desktop editions, Outlook on the web is basically much less functional – but with the “Emoji” button, the web app offers an exclusive feature that makes inserting smileys child’s play. This button, which can be found in the form of a smiling face directly below the message window, opens a quick menu that allows you to add various emojis to your e-mail with a single click. The smileys can be found under the heading “People and faces”:


You can also import your own smileys as images into Outlook on the web. Bing’s image search does not exist in the web app.

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