How to Type Curly Quotes and Curly Apostrophes

To present a professional appearance in print or to meet the style guidelines of a client, you may want to use true typographer quotation marks and apostrophes in your desktop publishing documents. These true quotation and apostrophe marks are curled left and right, unlike the straight-as-a-stick single and double quote mark show on a keyboard's apostrophe key. 

There are several ways to access and properly use curly quotation marks, also called smart quotes and proper apostrophes on a Mac or Windows PC.

Many software programs, including Microsoft Word, have settings you can use to enable or disable straight quotes or smart (curly) quotes automatically as you type. If you do not have that option in your software, you can make the change as you type. Below are the ways you can access smart quotes on a Windows PC, Mac, and in HTML.

To toggle the enable or disable feature in Microsoft Word for Windows:

1. Click the File tab.
2. Select Options.
3. Click Proofing in the left pane.
4. Click AutoCorrect Options.
5. Select the AutoFormat tab.
6. Check or uncheck the box in front of Straight quotes with smart quotes to toggle automatic smart quote replacement off and on.

To manually select smart quotes, your keyboard must have a numeric keypad. "Num lock" must be activated. To use the numeric codes, hold down the alt key and type the four-digit character code on your numeric keypad.

• Use ALT+0145 and ALT+0146 for the left and right single quotation mark or apostrophe, respectively. 
• Use ALT+0147 and ALT+0148 for the left and right double quotation marks, respectively.

Make sure you use the numeric keypad and not the row of numbers above the alphabet, the row of numbers will not work.

To toggle the smart quotes feature on a Mac in Word:

• Go to the Tools menu, click AutoCorrect, and then select the AutoFormat as You Type tab. 
• Select the checkbox for Automatically correct spelling and formatting as you type. 
• Under Replace as you type, select or clear the Straight quotation marks with smart quotation marks check box.

To manually select smart quotes, type the following keys simultaneously.

• Type Option+] and Shift+Option+] for the left (open) and right (closed) single quote mark or apostrophe, respectively.
• Type Option+[ and Shift+Option+[ for the left and right curved double quotation marks, respectively.

Web typography works a little differently. Smart quotes do not always work well on the web, so straight quotes are used a lot.

However, if you want to add curly quotes to HTML code, do the following:

• For the character for the curly single opening quote mark (or apostrophe) ‘ and ’, use ‘ and ’, respectively.
• For the character for the curly opening and closing double quotation marks, “ and  ’, use “ and ”, respectively.

Commonly, in current web design and print publishing, oversized curly quotes can be used to add interest to pull-quotes in articles or general information pages.

Straight quotes come to us from the popularization of the type­writer. In tra­di­tional print­ing and typesetting, all quo­ta­tion marks were curly. But type­writer char­ac­ter sets were lim­ited by me­chan­i­cal con­straints and phys­i­cal space. By re­plac­ing the curly open­ing and clos­ing quotes with am­bidex­trous straight quotes, two slots be­came avail­able for other characters.

The straight marks on the apostrophe key are also called primes. You can use the single straight mark for feet and minutes and the double mark for inches and seconds, as in 1'6" for 1 foot, 6 inches or 30'15" for 30 minutes, 15 seconds.