How to Insert Emoticons in Outlook
When you communicate with another person face-to-face, your facial expressions, body language and the emotion in your voice help set the tone of the conversation. When you communicate through email, you can't include these nonverbal cues. One way to help convey your tone in an email is to add an emoticon, such as a smiley face, to your message. Microsoft Outlook 2013 supports three standard emoticons by default, or you can insert symbols, pictures or use an Outlook add-in to add emotion to your email messages.
Microsoft configured Outlook 2013 to convert the following six common character representations of emoticons into three Wingdings font symbols: ":)" and ":-)" convert to a smiley face; ":(" and ":-(" convert to a sad face; and ":|" and ":-|" convert to a disappointed face. When you type one of these common text representations of an emoticon and press the space bar, Outlook's AutoCorrect feature immediately replaces the text with the appropriate Wingdings font symbol.
Another method of inserting an emoticon is to locate a font symbol from the Wingdings or another font and insert it into your message. First, click the location in the email message where you want to insert the emoticon. Next, choose "Insert" from the menu, select "Symbol" from the ribbon bar and choose "More Symbols..." Change the font selection to "Wingdings" or another font, and scroll through the list of characters until you find the emoticon you want to insert, then click to highlight it and select "Insert."
An emoticon that's not a font symbol is usually a picture file. If you save your favorite emoticons as pictures on your computer, you can insert the pictures into your Microsoft Outlook email messages. Select "Insert" from the menu, choose "Picture" and select the file. To insert a built-in smiley face picture, choose "Insert" from the menu, select "Shapes" and locate the smiley face shape in the Basic Shapes category. Drag the handles on the edges of the smiley face to adjust the size.
If you'd rather select an emoticon using a button that's part of Outlook, you can download and install a third-party add-on for Outlook with emoticon support. For example, Topalt Emoticons for Outlook is a free add-on that provides a single button you can click to insert an emoticon. Emoticons Mail includes more than 900 standard and animated smileys that you can insert. Handy Animated Emoticons from Scorpio Software is a collection of animated GIF emoticons that you can also insert into Microsoft Outlook messages (links in Resources).