Field guide / Rule 01 — Quotation marks
The quotation marks on your keyboard are not the ones a typographer uses. They are a leftover from the typewriter — and swapping them for the real thing is the single most visible upgrade you can make to a page of text.
A typewriter had one key for each quote — a vertical stroke that stood in for both the opening and the closing mark, because a machine with fixed keys could not afford two. Computers inherited that key, and so the straight quote (" and ') is still the default your keyboard sends.
Real typography never had that limitation. It uses four distinct marks — a left and a right for each — that actually point in the direction they open and close:
Two reasons. The first is legibility: curly quotes have weight and shape, so they sit with the rest of the letters instead of floating above them like stray tick marks. The second is meaning — a curly quote tells the reader whether it opens or closes, which a symmetric straight quote never can. Set well, they disappear; set with straight quotes, a page quietly announces that no one set it at all.
Every word processor ships a “smart quotes” feature that tries to do this as you type. It mostly works — and then trips over the cases below, which is exactly where a document gives itself away.
Here is the fact that untangles most mistakes: the apostrophe is not its own character. It is the closing single quote, ’. The same mark that ends a quotation also marks a contraction or a possessive — don’t, it’s, the studio’s work. Once you know that, the hard case follows naturally.
When letters or digits are dropped from the front of a word, an apostrophe stands in for them: the ’90s, ’twas, rock ’n’ roll. It marks an omission, so it curls like every other apostrophe — downward, ’.
Almost every smart-quote feature gets this backwards. Because a space sits in front of the mark, the software assumes you are opening a quotation and inserts a left curly quote — ‘90s — pointing the wrong way. Type designers wince; lawyers, who write the abbreviated the ’211 patent all day, wince harder.
It is a genuinely hard call, because the two are the same keystroke in the same place. Opening a quotation with a number is vanishingly rare, so a leading apostrophe before a digit is always an apostrophe — that one we fix without hesitation. Letters are trickier: ’twas is a contraction, but ‘tomorrow’ is a quoted word, and only the surrounding words tell them apart. So we curl a short, closed list of true contractions (’twas, ’tis, and the connective ’n’) and leave anything ambiguous as an opening quote, on the principle that a quiet miss beats a confident wrong.
Feet and inches, minutes and seconds, latitude and longitude do not take quotes at all — they take prime marks, ′ and ″, which lean to the right: 5′11″, 40°26′46″ N. This is the one place our engine will still curl a quote where a prime belongs, because 5′11″ and a genuine 5" of quotation are impossible to tell apart from the text alone. If your document measures things, it is the one mark worth setting by hand.
Paste any of these with straight quotes and you get the set version back — no settings, no find-and-replace:
Straight double quotes become directional — opening left, closing right.
An apostrophe is the closing single quote ’, mid-word.
A leading apostrophe before a digit marks elision — it curls down, not open.
The connective ’n’ is two apostrophes, never opening quotes.
Abbreviated numbers take an apostrophe — the case naive smart quotes flip wrong.
A closed list of true contractions is curled; ambiguous words are left untouched.
In short
Use curly quotes everywhere. Remember the apostrophe always curls the same way — ’ — even at the front of a word. And if you set feet, inches or coordinates, reach for primes by hand. Everything else, we handle on the way out.
Want to see it on your own text? Convert a document and read the cleanup report — every quote we curled is counted there.