Which translation of Augustine's Confessions is the easiest to read in English?

This question has long been of interest to me, and I've investigated it on a number of occasions in the past -- never quite in a "scientific" way, though. This looks to be a fruitful question, even if it is one of those "opinion based" (but hopefully "good subjective") ones that are not ideal for a Q&A in the StackExchange model.

Impressions

My own test passage of interest is the one where Augustine first encounters the Scriptures, in Bk. III, ch. 5(9). I've compared the translations listed here (perhaps not a comprehensive list, but close, I think) -- the letters correspond to the spreadsheet, below. I've appended some purely personal impressions of the "readability" of the translation; lower down there are some remarks on this passage itself.

• A. Augustine's Latin text
• B. E.B. Pusey (1838)
  Although the oldest of these translations, Pusey's handling of the Latin is often sharp and usually concise -- and somewhat archaic. Putting that together, the modern reader may well find this translation opaque. Worth a look, though, as it's easily and widely available.
• C. J.G. Pilkington (1886)
  Fifty years later, and while Pilkington's rendition doesn't appear that far from Pusey's, still the increased verbosity is apparent ... and without gaining much (that I can see) in "readability".
• D. F.J. Sheed (1948)
  Clocking in at about the same length as Pilkington, Sheed does represent a noticeable advance in fluency and ease of comprehension. He also takes more liberties with the Latin -- in several matters of detail, as well as the "flipping" of #8 and #9 in the "phrase" version of the text, below; and "grow in Your little ones" (#13) is a miss, as far as I'm concerned.
• E. Vernon J. Bourke (1953)
  Bourke shares some of Sheed's features, but without the idiosyncracies in comparison to the Latin. Not especially striking in its phrases, but clear.
• F. A.C. Outler (1955)
  In Outler's handling, the terseness of the Latin is unpacked a bit more, adding to the clarity, although I don't find his phrasing as graceful as some of these comparators.
• G. John K. Ryan (1960)
  At 166 words, Ryan's is the longest of these translations (the Latin is 98 words, and Pusey uses 140). The additional particles and modifiers make for clarity; I also find them a bit ponderous.
• H. R.S Pine-Coffin (1961)
  Pine-Coffin's rendering for the Penguin Classics is notoriously "free"; while this might lend to readability and the resonant phrase, it is a little farther from the Latin. It was the first version of the Confessions that I read (many years ago), and I still enjoy it, even with its foibles. It is "readable", to be sure!
• I. Rex Warner (1963)
  To my eye, Warner's translation flows as well as any here -- at least in this extract -- even if some find it a bit pedestrian.
• J. Henry Chadwick (1991)
  Henry Chadwick was one of the towering Patristic scholars of the 20th C., so his translation (done in his maturity) commands respect. He takes more liberties with metaphor, I think (see, e.g. his "mountainous difficulty" in #6, below), but they are different in kind from Pine-Coffin's.
• K. Maria Boulding (1997)
  Boulding achieves a degree of effortlessness in her prose not achieved by most. She has some occasional "padding", but usually to good effect. Not as literal as some, her choices on reflection tend to make sense.
• L. Benignus O’Rourke (2013)
  Adopting a highly distinctive approach, O'Rourke's translation is targetted at "young people", and laid out in strophes, as if poetic lines. It is accessible, and ofen striking. See below for a picture of this page in O'Rourke's handling, and an extract of a review of it.

_{UPDATE (13.10.2017) A new translation of the Confessions has appeared since this "answer" was posted, that by Sarah Ruden. See the end of this answer for her rendering of the test passage.}

The Data

Here are the texts for comparison. They are arranged chronologically from left to right; it's clear to see how the translations tended to grow in verbosity from Pusey's fairly terse start, not much longer than the Latin itself:

But this version makes it easier to do detailed comparisons (the text in blue is where the translator has transposed the sequence of phrases in English by comparison with the Latin in Column A):

Textual remarks

Beyond the impressionist sketches above, there are a few points in this brief extract which bring out the differences in our translators most sharply. (I refer to the numbered "rows" from the graphic immediately above.) ^{_{(What follows here is selective, not exhaustive!)}}

1. In #6 Augustine gives his mature characterization of Scripture -- not his first impressions, which he goes on to recount in ##7ff. The Latin has a poetic quality:

   sed incessu humilem,
   successu excelsam
   et velatam mysteriis.

   To my eye/ear, the translations which incline towards terseness are both "readable" and reflective of Augustine's diction here:

   lowly in access,
   in its recesses lofty,
   and veiled with mysteries; (= Pusey)

   Outler shares some of Sheed's language, but in with a better cadence (IMO):

   something lowly in the hearing,
   but sublime in the doing,
   and veiled in mysteries. (= Outler)

   (I'm not sure about "doing" for succēdō, but I'm not really competent to judge.) Chadwick here shows some boldness in extrapolating Augustine's implicit metaphor to arrive at a rendering that I find appealing and evocative:

   a text lowly to the beginner but,
   on further reading, of mountainous difficulty
   and enveloped in mysteries. (= Chadwick)

And, more briefly, a couple that come toward the end of this text:

2. #13 receives quite varied handling: verum autem illa erat quae cresceret cum parvulis, writes Augustine. Some of the attempts seem to me to be quite clunky:

   They were indeed of a nature to grow in Your little ones. (= Sheed)

   is not very successful, I think. Chadwick shows his propensity to expansion with this fairly clear rendering:

   Yet the Bible was composed in such a way that as beginners mature, its meaning grows with them. (= Chadwick)

   which is not yet nearly so elegant as Boulding's:

   Scripture is a reality that grows along with little children, (= Boulding)

   And I note that Warner's rendering is quite close to that, too.

3. #15 How to regard Augustine's self description as grandis in this final phrase? There are two general approaches to this:

   • "great one/big man": Pusey, Pilkington, Sheed, Ryan, Pine-Coffin
   • "mature adult": Bourke, Outler, Warner, Chadwick, Boulding
      

   Here, O'Rourke gives "sophisticated", which seems to me a clever way of implying both options. All of these options are "readable", but they construe the contrast Augustine is drawing here in different ways.

Towards "readability"

As promised, here is Benignus O'Rourke's rendering as it appears on p. 93 of his edition. It does make for a very readable version: all the more pity he decided to omit books X-XIII, then.

DISAPPOINTED BY THE SCRIPTURES

So I formed the intention
of reading the holy Scriptures
to see what kind of books they were.
And this is what I found, but only later:
something that was beyond the grasp
of the proud,
something not clear to the immature.
Something simple when one first encounters it,
but sublime as one advances.
Something shrouded in deep mystery.

At that time I was not the sort of person
to accept God’s word
to bow my head and follow its lead.
But in those days I did not think of the Scriptures
as I do now.
To me they seemed not fit to compare
with the dignified style of Cicero.
My bloated pride recoiled at their simplicity.
My mind failed to grasp their depth.

Scripture is such that it grows
with little ones even as they grow.
But I was too conceited to bear to be childlike.
I was swollen with pride
and saw myself as sophisticated.

Miles Hollingworth -- one of Augustine's many biographers -- reviewed it in Journal of Theological Studies, and this extract summarizes his judgment:

My impression is that by having aimed for a translation of plain readability that, as he hopes, a 16-year-old might enjoy, O’Rourke has also tapped deep into what made the original Confessions so winsome in their time. I found that I was deeply moved by his faithfulness to Augustine’s words. ... Scholars have long realized that each of Augustine’s words can take us far into the fascinating hinterlands of history and philology attached to them. But O’Rourke has chosen instead to look forwards, as Augustine the author did, when he sighted the audience whose souls he thought this book might save.

William Mallard's work, Language and Love: Introducing Augustine's Religious Thought Through the Confessions Story (Pennsylvania State Univ Press, 1994) included this thumbnail sketch on a variety of these translations:

Several English translations of the Confessions are available. The nineteenth-century Pusey translation remains a careful and vigorous text; yet its language is heavily archaic to the late twentieth-century ear. Two midcentury series of translated sources have included the Confessions in English: Vernon Bourke, noted Augustinian scholar, has offered a 1953 translation in the extensive Fathers of the Church series; Albert Outler, more recently a welcome authority on John Wesley, produced a 1955 translation in the Library of Christian Classics, vol. 7. The Bourke translation is a clear, literal rendering. The Outler includes helpful footnotes from time to time on major points of Augustinian thought. R. S. Pine-Coffin offers a paraphrase-translation in Penguin Books, valuable for rapid, initial reading. Comparable to Pine-Coffin is the Rex Warner translation of 1963 (Mentor Books); yet Pine-Coffin is superior in introduction and notes, and in the adept use of English, especially the striking phrase. J. K. Ryan’s translation for Image Books (1960) is a careful, close reading, yet contemporary in expression, with valuable notes, references, and introduction. Henry Chadwick has provided a new translation (1991) through Oxford University Press with especially helpful, knowledgeable footnotes, introduction, and index.

I note a recent undergraduate course on the Confessions at the Catholic University of America assigned the Chadwick translation as its set text (that syllabus has some useful further reading that would be of interest to anyone still reading this post).

If anyone is interested in the LibreOffice Calc spreadsheet with this data, you can view or download it from Google Drive. The sheet with the text broken into phrases/clauses uses Venturis ADF Condensed, available for free download (or see the whole family). (N.b. typos in the PNGs above have been fixed in the ODS file; I will update it with any further corrections, should that be necessary.)

And finally...

• Some fascinating glimpses into translations of the Confessions are offered in Steve Donoghue's review of the new Loeb edition/translation by Carolyn Hammond: "Book Review: The Loeb Augustine’s Confessions" (24 August 2014), and see also "omitted translations", below;
• Philip Burton, Language in the Confessions of Augustine (OUP, 2007) should really be noted here, and see also "omitted translations", below;
• A Reader's Companion to Augustine's Confessions, ed. by Kim Paffenroth & Robert Peter Kennedy (Westminster/John Knox, 2003) might be of interest to some;
• this question has been considered on the Catholic Answers forum;
• and is also posed on this "Great Books" webpage (using Wayback Machine to avoid the ad-popups on the live page).

Update (13.10.2017) Here is the rendering of the "test passage" from Confessions / Augustine; a new translation by Sarah Ruden. New York: The Modern Library, 2017.

Therefore I undertook to consider the sacred texts and get a sense of them. And lo and behold the subject matter wasn’t “factual” in pretentious people’s opinion, or laid straightforwardly bare for children’s eyes, either, but lowly when I stepped toward her, of lofty dignity when I came up close, and veiled in mysteries. But back then, I wasn’t the sort of person who could enter into her, or bend my neck submissively to follow her own strides. The tone I take now, you see, doesn’t show the way I felt when first turning to these writings, which seemed not even worthy comparing to the excellence of Cicero. My swollen-headed opinion of my own taste recoiled from their mediocre manner, and my critical eye couldn’t pierce into the qualities behind that. In actual fact, this writing is just the sort to grow up alongside small children, but I wasn’t going to stoop to being a small child; I was bloated with conceit and seemed to myself, anyway—quite grown up.

Omitted Translations

Now included in this answer for the sake of completeness.

• William Watts (1631) in the first Loeb edition of Augustine's Confessions, edited by W.H.D. Rouse (1912); see the "test passage" in Vol. 1, pp. 113-115. This was the basis for Pusey's translation.
• Philip Burton, The Confessions (Everyman's Library) (Alfred Knopf, 2001).
• Carolyn Hammond, Augustine, Confessions, (new) Loeb edition; 2 vols. (Harvard, 2014, 2016).