The 44 Most Stylish Films EVER

Photo Courtesy of MGM/UA Home Enterta!inment ©1968

       We know, we know….FORTY-FOUR?!  Sounds like a bit of an overblown, arbitrarily exhaustive number for a “best of” list.  And yes, we could’ve gone with the cliché top ten.  Or top twenty.  Instead, we thought of the films that came to mind first or that we watched the night before.  Rest assured that this list doesn’t have forty-four individual entries.  We’ve cheated and group many of them together, and we’re counting them all to pad the numbers and give the post and eye-catching tagline.

       Did we leave of a few?  Certainly.  Did we overlook painfully obvious examples of stylish leading men whose style nearly outshone the film itself (Cary Grant, anyone?) Absolutely.  Did we intentionally leave off staid period pieces in favor of relatively modern portrayals?  You bet your ass we did.

       North By Northwest notwithstanding, the following is not the ultimate collection of most visually-appealing,  well-costumed films ever to grace the screen.  These are the films we love to watch because, all else aside, we want to dress like the men in these films…period.  We’ll start with the most obvious choice…..

The ENTIRE Bond Franchise


With twenty-four films total as of publish date, the six (even you, Lazenby,) actors to carry the Walther PPK have proven to be the unquestionable archetype for men’s style ever put on celluloid.  While some of the installments have been better than others (cough…Tomorrow Never Dies…cough,) even the bad Bonds were still the best-dressed men in the room.  if we’re ranking the most stylish Bonds from top to bottom, it begins and ends with Dr. Henry Jones himself, Sean Connery, followed closely by Mr. Craig and Sir Roger Moore.  It falls off a bit after that, but Pierce Brosnan bats a decent cleanup.

The Ocean’s Movies


Sinatra.  Clooney.  Bernie friggin’ Mac.  The most dapper group of crooks ever assembled and spanning forty-seven years, two continents, and one Affleck, the Ocean’s franchise is second only to Bond, James Bond as the most enduring series of stylish leading men.  With the never-not-good George Clooney and the aforementioned Mr. Pitt killing it sartorially in every scene they’re in, we’d be remiss if we did not give a nod to the gods and pay homage to the original 1960 installment that started it all.  Though not as flashy and sexy as the Soderbergh-helmed trilogy, the Rat Pack version of Ocean’s is fun to watch, but is little more than Frank and the boys hanging out, drinking highballs, and chasing skirts (not that there’s anything wrong with that.)  Do yourself a favor and take notes anytime Don Cheadle is on the screen.  Just ignore the accent.

The Thomas Crown Affair (1968)


Steve McQueen is not considered the “King of Cool” for nothing.  This movie, along with Bullitt, The Great Escape, and LeMans are the reasons why.  If you’re ever looking to dress to the nines, or wondering how to rock the head-to-toe monochromatic look, this film is the first place you should go.  While McQueens’s accoutrements may seem a bit much (not everyone can sport a chained pocket watch,) there’s not a stitch out of place, nor a piece of clothing that doesn’t fit like a glove.  Especially the gloves.

The Complete Wes Anderson Oeuvre


       It comes as no surprise that throughout his career, one of cinema’s most stylish filmmakers has made some of Hollywood’s most stylish films.  In addition to creating visually-stunning, eye-pleasing productions, Anderson’s films have also featured cinema’s most well-suited (literally) characters, even if that suit is a red Adidas track suit or red ski caps.  Any man who can make an head-bandaged Owen Wilson or Gwyneth Paltrow in heavy eye makeup and fur overcoat look hip, has a gift and an eye that inspires.

The Godfather Parts I & II


What can be said about the Godfather saga that hasn’t been said repeatedly over the last forty years? Yes, the first two movies in the series may be the greatest movies in history, featuring possibly the greatest actor who will ever live (sorry, James Caan.)  While the acting, writing, and directing have all been lauded and awarded dozens of times over, the real thing to watch is the wardrobe:  Brando’s wedding-day tux, Pacino’s double-breasted beauties, and DeNiro, playing a young Vito Corleone, wearing one of the smoothest three-pieces ever to hang from a man’s back.  All of these make already amazing movies that much more enjoyable, and provide great inspiration for the capo-in-the-making.

(While the third installment didn’t earn inclusion on this list, some of  Andy Garcia’s looks warrant a quick glance.  You’re welcome.)


The Great Gatsby (2013)


           While the 1974 version featuring the great Robert Redford is no slouch, Baz Luhrmann’s 2013 adaptation featuring charisma-oozer Leonardo DiCaprio as the titular Jay Gatsby could’ve been more aptly titled Billionaire Throws Parties in Flawless Suits.  There’s a reason the film won Oscars for production and costume design, and it’s not because the production and costume designer is married to the director (she is.)  It’s because there is no point where Gatsby ends and the clothing begins; they are one, with the man not wearing the suits, but inhabiting them as if a part of his body (once again, see Grant, Cary.)  Gatsby is a prime example of how it’s not the PRICE of the suit that matters (which surely must’ve been exorbitant,) but the FIT that makes you look like a cool billion.  Well done, ol’ sport.

8 1/2 & La Dolce Vita


Lennon/McCartney.  Page/Plant.  Fellini/Mastroianni. 

Great things come in pairs, and Italian New Wave filmmaker Federico Fellini and his go-to lead, Marcello Mastroianni, are no exception.  All are classics, and remain to this day some of the most stylish films ever made, with Mastroianni reinventing the style wheel and ushering in a new era of flawed antihero. If you watch for no other reason, check out the iconic shades he dons in 8 1/2 (Otto e mezzo) and then go out and find some.  Thank us later.

The Fifth Element


   Let’s get one thing out of the way:  Ruby Rhod and his annoying, shrieking, blond wig-wearing ass nearly ruined what was one of the best and most visually-stunning movies of the nineties.  That being said, The Fifth Element featured a stylish villain (played by accent chameleon Gary Oldman,) a stylish heroine (Leeloo Dallas, mooolti-pass,) and the coolest blue alien/opera singer/deus ex-machina outside of Blade Runner.


A Hard Day’s Night


The Beatles’ first foray onto the big screen may also be the best four suits ever seen on film at one time.  Thanks in part to SoHo tailor Dougie Millings and Savile Row craftsmanship, the film was the beginning of the Beatles’ reign of sartorial supremacy that lasted the rest of the decade.  While the Sgt. Pepper military coats still look as iconic as they did in 1967, look no further than the early days of Beatlemania to see the lads from Liverpool at their most sharply-dressed.  While we’re partial to John musically, do yourself a favor and steal George Harrison’s black-on-black look.  While he may have been The Quiet Beatle, he was also the most stylish.


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