Smileys, or emoticons, are small images that express emotion via email, instant message or Internet postings. Some email programs come with pre-installed emoticons. However, there are also endless emoticons you can download online. If you're looking for more smiley emoticons to insert into your Outlook Express emails, you can download them for free at various emoticon sites that are meant to work with Outlook Express.
Download and install PostSmile (see Resources for link), a free program that allows you to insert smileys into your Outlook Express email. To use the program, open a new message in Outlook Express, then place your cursor where you want to insert a smiley. Open PostSmile and find an emoticon you want to use, then select the smile and drag it into the email message.
Download and install Bandoo (see Resources for link), which provides free animated emoticons, smileys and winks for email and messenger programs. Open a new message in Outlook Express and you'll see a Bandoo toolbar available, which you can use to add an emoticon to your message.
Download and install Smiley Central (see Resources for link), which is a free toolbar that will be automatically installed in your web browser, instant messenger and email programs, including Outlook Express. To add a Smiley Central emoticon, open an Outlook Express message and click on an emoticon from the Smiley icon on the new toolbar.