Software & Apps MS Office How to Insert Emoticons in Outlook.com and Hotmail Share emotions in your email messages by Heinz Tschabitscher Writer A former freelance contributor who has reviewed hundreds of email programs and services since 1997. our editorial process Heinz Tschabitscher Updated on February 26, 2020 MS Office Outlook Word Excel Powerpoint Tweet Share Email Emoji express emotions and concepts in a fun and quick way. Classic emoticons like :-) or :-O are only characters. Take smileys one step further with Outlook Online or Outlook Mail on the web using your Outlook.com, Live.com, or Hotmail.com email address and insert graphical emoticons in your messages. Instructions in this article apply to Outlook Online for Microsoft 365 subscribers, and Outlook on the web for Outlook.com, Live.com, and Hotmail.com email accounts. Add Emoticons to Outlook E-Mail Messages Use the built-in emoji tool to add expressions to emails with just a few clicks. Open a New message, Reply to a message, or Forward a message to open a new email in the Reading Pane. Lifewire Position the cursor where you want the emoji to appear. In the Formatting toolbar, select Insert emojis and GIFs. Lifewire In the Expressions pane, select Emojis. Lifewire To search Bing for a short video expression, go to the GIFs tab and enter a keyword in the Search box. Select the emoji you want to insert. Enter a keyword in the Search box or the browse the Category tabs to find the emoji you want to use. The emoji appears in the email message. You can copy and paste an emoji just like other text. For example, copy an emoji in the message area and paste it in the email subject field.