Draw a Box on Picture in Outlook
How to insert winking/blithe emotions (smiley faces) in Outlook?
Generally speaking, yous can easily insert normal smiley faces past symbols or AutoCorrect feature in Outlook. However, some users may desire to insert winking smiley faces or blithe emotions to light upward their emails as those in conversation apps. Hither, this commodity volition introduce the mode to solve this trouble.
Insert winking/animated emotions (smiley faces) in Outlook
Salvage winking/blithe emotions (smiley faces) as AutoText for reusing with only one click
Insert winking/animated emotions (smiley faces) in Outlook
This method volition guide you to configure the AutoCorrect settings to automatically replace specified text with a winking smiley face up or animated emotion, and so hands insert winking/animated smiley faces by tying the specified text in Outlook easily.
Note: Before below steps, you take to salvage the pictures of winking smiley faces or animated gif images on your hard discs. If you haven't, you can salvage below pictures every bit yours:
1. In the Mail view, click Home > New E-mail to create a new email.
two. In the new Message window, delight click Insert > Pictures. Meet screenshot:
iii. In the Insert Picture dialog box, please (i) click to open the specified folder you relieve the pictures of winking smiley faces or animated emotions in, (2) select these pictures, and then (iii) click the Insert button. Run across screenshot:
4. Now these moving-picture show or gif images are inserted in your email. Please select 1 of them, and click File > Options.
5. In the Outlook Options dialog box, click Mail in the left bar, and then click the Spelling and Autocorrect button in the Compose messages section. See screenshot:
6. In the Editor Options dialog box, click Proofing in the left bar, and then click the AutoCorrect Options button in the AutoCorrect options department. Come across screenshot:
7. Now you go into the AutoCorrect in Email dialog box, please do every bit below screenshot shown:
(one) Click the AutoCorrect tab;
(ii) In the Replace box, type the specified text which will be replaced with the selected film or gif paradigm;
(iii) Check the Formatted text choice;
(iv) Click the Add together button.
8. Click the OK button successively to close all dialog boxes.
nine. For adding other winking smiley faces or blithe emotions, delight echo above Step four-viii.
From now on, when you type the specified text and printing the Enter primal in emails, the specified text will be replaced with the selected picture show or gif paradigm automatically. Meet screenshot:
Note: This method cannot insert winking smiley faces or blithe emotions into subjects. Please click here for solution of inserting smiley faces in subject area.
Save winking/animated emotions (smiley faces) as AutoText for reusing with merely one click
If you have Kutools for Outlook installed, you can salve all inserted winking smiley faces or animated emotions as AutoText entries with the AutoText characteristic, and and so reusing them easily in time to come with merely one click.
Kutools for Outlook: Add together more than than 100 handy tools for Outlook, free to try with no limitation in 60 days. Read More Free Trial Now
1. In the Mail view, click Home > New E-mail to create a new email, so click Insert > Pictures in the new Message window. See screenshot:
2. In the opening Insert Pic dialog box, delight (i) open the binder containing winking smiley faces or blithe emotions, (2) select them, and (3) click the Insert push. Encounter screenshot:
And now the winking smiley faces or animated emotions are inserted into the new email.
3. (i) Select one of winking smiley faces or animated emotions, (2) click the Add push button 
in the Car Text pane, (3) type a name for the new entry in the Auto Text dialog box, and finally (4) click the OK push. See screenshot:
Notes:
(1) The Car Text pane is provides by Kutools for Outlook, and it's enabled in message window by default. If the pane is invisible, please click Kutools > Pane to enable it.
Kutools for Outlook: Add more than than 100 handy tools for Outlook, gratis to endeavour with no limitation in 60 days. Read More Free Trial Now
(2) This pace will add together ane picture equally AutoText entry. For adding more than winking smiley faces or animated emotions, delight repeat this step to add one past one.
Now the winking smiley faces or blithe emotions are saved as AutoText entries, y'all tin easily insert them with clicking the Insert button 
behind them.
Demo: Insert winking/animated emotions (smiley faces) and save as AutoText entries
Tip: In this Video, Kutools tab is added past Kutools for Outlook . If you demand it, please click here to have a 60-day free trial without limitation!
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Source: https://www.extendoffice.com/documents/outlook/4504-outlook-winking-animated-emotions.html