Look at the key next to your Enter key. The straight ” it types isn’t a true quotation mark. It’s a compromise left over from the typewriter, and it’s the reason typographers wince at most text on the internet. Real quotation marks are curly, come in pairs that face different directions, and look different in every language.

A Short History of Quotation Marks

Quotation marks are a surprisingly late invention. Ancient Greek and Roman writing had no way of showing that words came from someone else. The closest thing was the diple, a small sideways arrow (>) placed in the margin by scholars at Alexandria to flag a passage worth noticing, and later used by early Christian copyists to mark quoted Scripture.

For centuries, quotes were handled in other ways: a change of ink color, a new line, or a phrase like “he said.” Printed quotation marks start to appear in the 16th century. Early printers placed them at the left margin, repeating the mark at the start of every line of a quoted passage, which is the origin of the “blockquote” look.

The shape settled into the form we use today, small marks that resemble commas, either raised or inverted. Opening quotes look like tiny 6s, and closing quotes look like tiny 9s, which is why they’re nicknamed “66 and 99” quotes. Other languages developed their own conventions, so the same idea is written differently around the world.

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Anatomy of Quotation Marks

Quotation marks are built from commas. A single quotation mark is one comma-shaped mark, raised to the top of the line. A double quotation mark is two of them side by side.

Curly (typographic) quotes are different on each end. The opening mark has its head at the bottom and its tail rising, like a “6.” The closing mark is flipped, head at the top and tail curving down, like a “9.” The closing single quote is also what’s used as an apostrophe, which is why apostrophes in curly-quote text look like a tiny 9.

Straight (typewriter) quotes are vertical marks, usually wedge-shaped or rectangular, with no difference between opening and closing. They’re the ones on your keyboard.

The height of the marks matters. They usually align with the cap height or the ascender height, hanging from the top of the line. The gap between the two marks in a double quote is a delicate decision: too tight, and the two marks merge; too loose, and they look like two separate apostrophes.

Designing Quotation Marks From Scratch

Designers draw quotation marks after the comma, since the same head and tail shapes carry over. The comma is rotated and raised to create the closing quote, then flipped to create the opening one.

But an exact rotation almost never works. A comma drawn to sit below the baseline has its weight in the head and its tail at the bottom. When the same shape is moved to the top of the line, the visual weight can feel off, so designers redraw the proportions slightly so the marks look balanced at the cap height.

Designers also design both curly and straight versions. Straight quotes get a tapered, wedge-like shape in many typefaces, which looks sharper and more modern than a plain rectangle. They need to remain readable at small sizes, since they’re also used for inch marks and in code.

Spacing is the last challenge. A quotation mark often comes right before a capital letter, a lowercase letter, or a punctuation mark, so the surrounding spacing has to work in many combinations. Pairs like “T” and a closing quote, or a period followed by a quote, often need individual kerning.

Unique Facts About Quotation Marks

Straight quotes are technically prime marks in disguise. The straight single quote (‘) is a stand-in for the foot mark, and the straight double quote (“) stands in for the inch mark, as in 5’10”. Typographers use true prime marks (′ and ″) for measurements, but almost nobody has a key for them.

The straight quote is a legacy of mechanical limits. Typewriters had a small number of keys, so one straight quote key did triple duty as a double quote, an apostrophe, and an inch mark. Computers inherited the habit, and many programming languages still require straight quotes, since curly ones are treated as different characters and cause errors.

Different languages quote differently. English uses ” ” and ‘ ‘. French uses guillemets, « like this », which are often said to be named after the 16th-century French printer Guillaume Le Bé, though that origin is debated. German writes „like this“ with the opening mark at the bottom. Japanese uses corner brackets, 「like this」.

Quotation Marks in Popular Fonts

In Garamond and other old-style serifs, the curly quotes have round heads and curved, tapering tails, echoing a broad-nib pen’s stroke. Helvetica uses compact, heavier marks with a short tail, matching its neutral character. Futura keeps the marks small and nearly geometric, with tails that are barely curved.

In script and display fonts, quotation marks are often oversized and decorative, used as graphic elements in pull quotes and posters.

Summary

Quotation marks were a late addition to writing, started as a scholar’s margin note, and settled into comma-shaped pairs that look like tiny 6s and 9s. Most of the marks you see online are straight stand-ins from the typewriter era, which is why real typography treats curly quotes as a mark of care. Designing them well takes more than rotating a comma.

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