Should punctuation surrounding italicised words be italicised?

This might be a tad off-topic, but I am looking for an English-specific answer.

When I’m using italic text to denote emphasis or a quotation, should the italicisation extend to the punctuation surrounding the italicised words? If the punctuation marks are not italicised, in most digital fonts the italic letters will crash horribly—or at least intrude awkwardly—into the Roman punctuation. It’s especially problematic with parentheses, and lowercase Fs. Since I don’t have the luxury of typesetting all of my documents in lead, I’ve taken to either italicising the punctuation, or inserting a thin space (for lowercase F) or a hair space (for other letters) before the closing punctuation.

Examples:

• What is that? ⇒ What is that? ⇒ What is that ?
• Solid (or fluff). ⇒ Solid (or fluff). ⇒ Solid (or fluff ).
• (Good times!) ⇒ (Good times!) ⇒ (Good times !)

I know this is a nitpicky thing (hell, even I think so, and I’m the one asking), but is there a standard way to address it? Just because this is the internet, it doesn’t mean we need to totally disregard the typesetting facilities that are available.

The Chicago Manual of Style (14th Ed.) has this to say about it:

5.4: The typographic treatment of punctuation adjacent to a variant font (italic or boldface within roman text, for instance) should be governed by both appearance and meaning. Generally, punctuation marks are printed in the same style of font of type as the word, letter, character, or symbol immediately preceding them.

5.5: A question mark or exclamation point that immediately follows an italicized title and that is not part of the title should be set in roman to avoid misreading.

5.6: Parentheses and brackets enclosing italic material may be set in italic to avoid such common typefitting problems as overlapping ascenders or descenders or visually uneven spacing within enclosures. When the enclosed material begins and ends in italic but contains roman text in between, italic enclosures may be used. If only one end of the enclosed material is italic, however, the parentheses or brackets should be roman.

Looking at your examples, therefore, I think option 2, then option 1 or 3, then option 2 are the best choices.

In some traditional typesetting contexts, you would never italicise parentheses even within italic text (and I'd recommend doing this yourself if you have the luxury). I must highly recommend not to only italicise one of the parentheses! (As in your example ‘(or fluff)’.)

Otherwise I agree with the other comments on ‘it depends’, according to aesthetics and ambiguity of the text. Just make sure you're consistent.

Finally, your use of the thinspace is to be highly commended. Keep it up.

I realise this is an old post, but I was searching for guidance on this issue myself, and, unfortunately, things have changed.

The Chicago Manual of Style, 16th edition, now says (§6.2) that punctuation surrounding a word or phrase should be in the font of the surrounding text, unless the punctuation is part of the text in question (e.g., the movie title Help!). Section 6.4 further says about italicising adjacent punctuation:

According to a more traditional system, periods, commas, colons, and semicolons should appear in the same font as the word, letter, character, or symbol immediately preceding them if different from that of the main or surrounding text. [...] This system, once preferred by Chicago and still preferred by some as more aesthetically pleasing, should be reserved—if it must be used—for publications destined for print only.

Sigh. This style looks like crap to me, but I suppose there's no fighting it.

Logically, it depends on whether the punctuation belongs to the italicized text or to the rest of the sentence.

• He asked, "Why?".
• He asked, "Why! Because it is not obvious to me why."

(And yes, we can debate the presence of the full stop in the first example - where 'full stop' gets translated to 'period' in American English.)

If you are going for publication, then 'House Rules' probably take precedence over 'logic'.