How to Insert Emoticons in Outlook and Hotmail

An emoji keyboard.
Emoji keyboard. Dimitri Otis/Getty Images

You can use emoji to express emotions and concepts in a fun and quick way with Outlook Mail on the web at outlook.com and Hotmail. Classic emoticons like :-) or :-O are characteristically only characters. But with Outlook Mail on the Web and Outlook.com, you can take smileys one step further and insert graphical emoticons in your messages.

Insert Graphical Smileys (Emoji) into Emails with Outlook Mail on the Web

To use emoji and other graphical emoticons in an email you are composing in Outlook Mail on the web at outlook.com:

  1. Click New in Outlook Mail on the web to start a new email. (Of course, you can reply to a message, too, or forward one.)

  2. Position the text cursor where you want to insert the graphical emoticon.

  3. Click Emoji in the toolbar at the message's bottom.


  4. Click the emoji, symbol or icon you want to add to your email's text from the sheet that has appeared. Use the category tabs at the sheet's top to open various collections of emoji. The Recent (🔍) category lists emoticons you have used recently. Also on the Recent tab, you can use the search field to find a specific emoticon; type "wink", for example, to find winking faces, "pig" for pig's faces, or "avocado" to not find an avocado.

You can copy and paste inserted emoji like other text. Try pasting one to your email's subject field, for example. Outlook Mail on the web will send the emoji—if it is in the message's body—as an image attachment, so it should show in some form for all recipients. It will not include a plain text alternative form (say, ;-)), though.

Insert Graphical Smileys (Emoji) into Emails with Outlook.com

To insert a graphical emoticon into a message you are writing with Outlook.com:

  1. Click New to bring up a new email. (​You can also reply to a message you have received, of course, or forward.)

  2. Position the text cursor where you want the emoji to appear.

  3. Click Insert emoticon in the message's formatting toolbar.

  4. Now select the emoji, graphical smiley or icon you want to insert into your email from the list that has appeared.​ Use the category tabs on the list's top to find the appropriate emoji. The Recent category lists emoticons you have recently inserted in emails using Outlook Mail on the web.

Insert Graphical Smileys in Your Windows Live Hotmail Messages

To insert graphical emoticons in a message with Windows Live Hotmail:

  1. Click New in Windows Live Hotmail to start a new email message.

  2. Put the insertion mark where you want the emoticon to appear.

  3. Click Emoticons under Insert: right above the message's formatting toolbar.

  4. Now click the icon you want to insert into your Windows Live Hotmail message from the list that appears to the right.

You can delete a graphical Windows Live Hotmail emoticon like regular text.