Woody is never far from my thoughts, even though the last film of his I saw was probably that thing with Scarlet Johansson.  I remember, early on, at our local Odeon, being baffled by 'Stardust Memories'. 
The nightclub routines (are they available now on CD?  I listened to them on a double cassette) are a joy.  Quite cruel but quintessential Jewish humour.  I love his account of the run-in with the neighbourhood bully and the ant that Woody has named 'Spot'.  Reminds me of growing up where I did, where the ownership of a book or two was met with undisguised contempt, much less playing the cello. 
As for that slightly rumpled, crumpled, un-co-ordinated look I cast aspersions on back then, well, I think Woody had it nailed all along.

Woody is one of the last links to the golden age of New York entertainment.
Going back to the Nineties New York was still awash with jazz and cabaret clubs. In one long weekend I saw Booby Short at Cafe Caryle, Houston Person at the Village Vanguard, an open mic stand up show and Iris Williams at the Oak Room. There was just so much available for grown ups.

I've just been dipping into the Marion Meade biography, which I last read from cover to cover ten years ago.  I like his sloppy look more and more - there are a number of black and white photographs. 
I took another look at 'Annie Hall' last week and noted spread collar after spread collar.  I especially liked the teaming of a tartan shirt with an Argyle slipover.  Pure nerd. 
If you're a totally committed fan, though, don't read Ms. Meade's book (which is excellent).  Woody comes across as a total arse.
I also read - for the second time - Anita O'Day's 'autobiography' recently.  I wish I hadn't.

Dig jack_sparrow over on The Wardrobe - a very old thread indeed - just discussing his look before FAME grabbed him by the balls.  Cheeky chips in (an early favourite of mine; where is he now?).  That tweed jacket-plaid shirt-jeans-sneakers vibe was straight out of East Village jazzing circa 1960, wasn't it?  Or something not unlike it.

Never a fan of O'Day. I always felt she was too showy.
There are so many singers of that generation worth a listen to:
Jeri Southern Coffee Cigarettes and Memories, Jo Stafford + Jazz, Julie London Around Midnight, Carmen McRea Torchy and June Christy Something Cool.
Peggy Lee's Mink Jazz has a lot of fans too
I also really like Shirley Horn. Her later work on Verve is well worth checking out.

Returning to the subject of Woody Allen, Marion Meade's biography is worth reading for anyone who digs the hedonistic NYC background (it can be viewed with pleasure only from a safe distance, I think), although barely anything else.  I suspect a good deal of it is nothing more than semi-educated guesswork.  How could she know he drank coffee and orange juice the morning after an Oscar ceremony ('Annie Hall')?  Rather like a recent biography of Sinatra I abandoned it reminds me of the historical biographies I once read in which the author knows just how many flagons of small ale Elizabeth Tudor drank at a sitting.

There are - does it really need stating? - a number of 'blogs' exploring Woody's look over the years (with an understandable, I suppose, emphasis on 'Annie Hall'), including his wearing of 'acorn' jeans by, I think, Abercrombie and Fitch and an expensive (way too expensive) plaid shirt by Alexander McQueen. 
It all slightly contradicts Marion Meade's descriptions of his 'lumpy' sweaters and rumpled cords - or does it? 
Many, many years ago one of our (former) posters referred to Woody's 'mouldy fig' look - then, just the other day, I stumbled across a reference to 'trad' (but mostly in terms of his musical tastes: did he eschew bebop and all that followed just as surely as he rejected Presley, Lennon and Dylan?). 
I keep exploring.