Agree w/ Connery's Bond as noted above - Black Grenadine tie w/ white shirt/light grey 3 piece definitely makes my top three. If CG's North by Northwest grey suit/white soft collar shirt/silver grey tie is #1, then McQueen's (original Thomas Crown) grey plaid w/ light blue shirt, sky blue tie has to be #1A. The only thing about CG's suit that doesn't quite suit me is that it is ventless, but it's hard to argue with perfection.
La dolce vita and several other Fellini movies...
North by Northwest
Wallstreet 1 & 2
The wrong man ( not because of Henry Fonda but because of Anthony Quayle)
Scarface( for douchebag styleÂ² with serious man cleavage)
The King's Speech
All the James Bond movies featuring Sean Connery and Pierce Brosnan. * Sean Connery in Conduit suit with narrow ties and Turnbull and Asser shirt - Dr. No (best quote: "Interesting. Where were you measured for this ? My tailor. Saville Row. Is that so? Mine's a guy in Washington") - From Russia with Love - Goldfinger - Thunderball - You only live twice - Diamonds are forever. and... non-canon version of Never say never again. (Connery is not wearing a suit that much in that movie) * Brosnan era - British spy in a British shirt (T&A) and shoes (Church's) but in Italian suit (Brioni) - Golden Eye: I especially like the scene when Brosnan stops the tank to fix his tie and to chase the Bond girl and villain. - Tomorrow never dies - The world is not enough: Even casual suit (beige suit with brown monkstrap and blue shirt in Istanbul scene) is nice - Die another day: here Brosnan is turning to Brioni shirts instead of T&A Wouldn't recommend George Lazenby and Roger Moore. Lazenby wearing a skirt (maybe a traditional Scottish costume I guess) is ugly. Roger Moore's suit in the 70's and 80's have wide and low-gorged lapel with flared pants reflecting the fads in those days. Timothy Dalton's suit is nice, but sometimes seems a bit awkward. Daniel Craig is ok, but his muscular physique rather makes him look less elegant. Body of lies (suits are from Huntsman) is also nice. If interested in Armani suit in the early 80's, watch American Gigolo. You wouldn't dare to those suits these days.
Good summary sage, I agree with most of that but Connery looked dire in DAF (early scene in Blofeld's mud lab in baggy tweed, breaking into Willard whyte's retreat in cream suit and short pink tie etc.)
Incidentally Brosnan was contractually forbidden from wearing a tux in any other film while he was Bond. In TTCA he is seen at the jazz club in a tux but with an untied white bow tie. Very close to the edge but the producers were the same as the Bonds at the time so they let him slide with his near-tux.
Cary Grant's suit in NBNW looks blue-gray but is really a very muted glen plaid which I only realized from seeing photos in the book about his style, not from seeing the film countless times. I like ventless jackets but hate 3 roll 2s, (completely pointless) but like you say he makes it work and his long semi spread shirt collar looks great.