Introduction to the List of Films

Why History Matters

Schoolboys, To Serve Them All My Days and School Ties

History is what gives meaning to an item, and the power of style is in the meaning of clothes just as much as in their appearance.  Today, when class and other social structures are much less acknowledged, we rarely think consciously about what clothes can mean.  All items of classic menswear, however, have a history rich in significance.  Knowing this history lets you know what an item or combination means, and knowing that helps you better craft the message you send with what you choose to wear.

For example, the combination of a blazer and a striped tie with grey flannels or chinos has long been a uniform at many elite prep schools for WASP children, the offspring of the American northeastern establishment who go on to university at, inter alia, Harvard, Yale and Princeton.  Many who are not consciously aware of this connection still sense the youth and class associations when they see this ensemble.

Blazers from the water, to the pitch, to student-life in general, to ...

The historical connotations, however, go much deeper than that.  Blazers originated at early 19th century rowing competitions at Oxford and Cambridge, characterized by bright colors and/or bold stripes.  They were soon worn by spectators and as warm-ups at other upper-class sporting events before eventually being worn daily in casual, sporty combinations by Oxbridge men.  Their brass buttons and currently most popular and quite conservative solid navy color crossed over later from British naval uniforms.  The striped tie has its history in the ties identifying exclusive schools, clubs, and military regiments in the U.K.  Flannels, like blazers, come from 19th century English sportswear, when blazers were themselves often flannel.

Students at Phillips Academy in Massachusetts

By the early 20th century, this combination was the uniform of schoolboys at some of Britain's elite private schools, which, to Americans' confusion, they call "public" (to distinguish them, centuries ago, from schools run by the church and by guilds).  American prep schools were, and still are, in many ways imitations of the English public schools, from their frequently Gothic architecture to their uniforms.  Though chinos originated in British military uniforms of particularly imperial operations, it was the Americans who replaced flannels with chinos in the school uniform after American GIs returning from WWII established them in civilian dress vocabulary.

Thus, not only does the ensemble have powerful associations in its American prep-school expression, its elements reveal the deep Anglophilia of the rich Americans who established it on this side of the pond around the turn of the last century.  All of its connotations: English public schools, Oxbridge, elite water sports, soldiers, sailors, empire, and WASPs prepping to study at Yarvton, make this ensemble a potent and popular, if not clichéd, one for Americans.

Mod subversion of the blazer
(Quadrophenia)

Generally the ensembles traditionally preferred by American men share a similar England to northeastern U.S. pedigree.  My list of films follows the slow westward drift of the lineage of classical tailored men's style from Versailles to London and the British countryside, then to the Boston-Washington corridor and its colleges, all the way to Hollywood. Understanding why and how clothing expresses power comes in knowing lineage. The history of almost every detail, garment, and standardized ensemble can be examined to see how they impart meaning in their current use.

Meaning is not only created by the rich and powerful of the establishment.  Further layers of meaning are also developed in reaction, rebellion or ironic use, such as when working class youth in the U.K. appropriated the boating blazer in the 60s.  To understand what a detail, garment or ensemble means today, you must know where it came from.  This will also give you ideas on how it can be deployed in new or more traditional ways in your own style.  If you have not yet read my essay on the history of men's style and style anxiety, you may want to read it before beginning the films.  You should also seriously consider the historical books I recommend at the bottom of the page to accompany your viewing of the films recommended here.


Why Films?

T.R. Devlin, Notorious

Films not only present a detail, garment and/or ensemble at a certain point in history, they also present it on a character determined by many specifics such as class, age, personality, occasion, and occupation and in the course of carrying out specific actions or pursuing specific goals.  Paying attention to these contextual details teaches you critical information you need to make use of the history of men's style and to understand what it means to dress for occasion.

If you really want to learn about men's clothing by watching films, you must always pay attention to the context of any garment and ensemble.  When you see a character wearing a specific garment ask yourself why he would be wearing it.  Who is he?  What is his social rank?  What is the occasion, location, season, time of day?  Simply knowing that men wore an item in a specific decade is far less useful than knowing on what occasions, where, with whom, and, thus, why and how, they wore it at that point in history. Men wore dress (tail) coats in the 1810s, 1880s, and 1950s, with some continuity of function but also with very different meanings in the three decades.  Reading the historical books I recommend below along with your viewing will give you much more detail to watch for and more understanding of what you are seeing.


What to Look for as You Watch

Paying attention to the aspects listed below will teach you far more about how men's style has developed than simply sitting through the films.  To get the most out of your viewing, these are elements you should always be aware of with the character wearing each detail, garment and/or ensemble:

Young Old Money in English style amid English architecture
in their New Haven in a New England

CLASS.  This is critical as much of the power of clothing comes from class associations.  Though Americans are generally uncomfortable discussing let alone acknowledging class, it plays a determinant role in the meaning of clothes.  What you wear cannot help but to broadcast class signals, even if they are only sent accidentally and received subconsciously.  Thus, I will take a little extra time to discuss the idea of class as it relates to men's style.

I propose six classes to offer you a simple way of categorizing what you are seeing in the films.  Most of the names I give these six classes are not universally applied the way I am using them and can mean quite different things to different people.  These six classes are distinguished by their income, though that criterion is dangerously misleading.  Class is not equivalent to money, however intricately related the two may be.

Class is primarily about the following characteristics: mindset, habits, worldview, and manners.  These, in turn, are shaped by generations of: 1) security, 2) luxury, and 3) political power - or their lack.  That is, the characteristics of class are developed out of the abundance or lack of these three things to which money gives access.  Again, class is related to money but not equivalent to it.  Those characteristics can last in families or individuals after money has dwindled, or can be lacking in those with new wealth or an unawareness of how wealth has traditionally been used by the higher classes.  Generally, though, one's class identity is most stable when both money and class characteristics are commensurate.

Each of my six classes is a very simplified generalization and could be further subdivided into gradations and varieties.  They also do not necessarily take into account the powerful effect of race, immigration and other factors on the status of an individual.  A single film character (just like a real man) can express characteristics of multiple classes for any variety of reasons.  As oversimplified as they are, I offer my six classes as a starting point for considering class interactions as you watch the films.  I group them into two groups of three.  The critical distinction between my top three and the bottom three classes is the source of one's income: wealth or work.

Income from wealth is enjoyed by those owning so much capital and having such significant investments that their income is produced continuously by this wealth, not from a job.  That is, the money they already have makes (as interest or other earnings) the money they live off of day to day.  These make up less than the top one percentile in America, though they have very significant political power including the ability to shape the political debate to steer the attention and votes of the masses.  They generally maintain and grow their wealth within their families, a dynamic that produces both the advantageous power and prestige of belonging to such a family and the considerable pressure to expand, or at least maintain, familial wealth and respect.  I call those who live from wealth the "leisure" classes though it is not at all uncommon for them to pursue occupations.  I consider their lives leisurely because such work, if pursued, is done more out of personal fulfillment than of financial necessity.  Hierarchy within the leisure classes is based primarily on non-monetary considerations such as how many generations one's family has been in the leisure classes, how long and the degree to which one's family has been involved in supporting and leading philanthropic institutions (universities, hospitals, museums, charities, etc.), membership in certain clubs and attendance at certain schools, and even more obvious factors like legal nobility.  Though overwhelming wealth can give one considerable power and even quick access to many institutions, it cannot make up for a lack of family history, philanthropic leadership, generations of affiliation, and inherited titles.  Thus, among the leisure classes, wealth alone is not the primary determinant in establishing hierarchy - generations of time using wealth to participate in the right institutions in the right way is.  While an impoverished blue blood cannot maintain for long preeminence any more than a fantastically rich but socially lost newcomer can quickly gain it, the two types often benefit from combining their assets through marriage.  At the very least their children, connected and rich, will have a firm footing.  These are the three leisure classes I recommend you think in terms of as you work through the films:

Fitzwilliam Darcy, Pride and Prejudice
Duke of Windsor, Edward & Mrs. Simpson

1. Aristocracy.  There is no legal aristocracy in America, so we are talking about men from the Old World here.  These men come from families with wealth based originally in land - often meaning many, many thousands of acres - that earns (or once earned) continual rent from its numerous tenants.  English aristocrats live within an intricately complex system of many levels.  There is a great difference between the monarch and a baronet and between a baronet and a simple landowning gentleman.  In fact, there can be a great difference just between two gentlemen (as between the rather wealthy Mr. Darcy and the modestly comfortable Mr. Bennet in Pride and Prejudice).  Nobility is inherited by individuals, not entire families, so even descendants of monarchs can be untitled - and thus legally commoners - but still part of the aristocracy.  The gentry, or lower aristocracy, also have no titles.  Should an English aristocrat in a film lack a title, you can best recognize him as an aristocrat if he lives in leisure off of landed family wealth.  As for their access to the three factors that determine class: political power, luxury, and security, aristocrats are at the top of the game.  The aristocracy at one time had all and continues to have a significant portion of political power in the U.K.  They have had centuries to develop strict codes of how to play with their luxury - including their dress.  And despite two centuries of serious erosion to their fortunes and financial security, these are still generally beyond question.  Until after the world wars they set the style standards that trickled down to men of all other classes, which is why films about them up to WWII are crucial for our purposes.

Henry Wilcox, Howards End
Linus Larrabee, Sabrina

2. Old money.  Such men come from families that established productive wealth at least a generation or two earlier.  In England the equivalent would be families that established their wealth in business or banking since the beginning of the Industrial Revolution (rather than earlier through land as aristocrats).  Families with industrial age wealth are not considered "old" money in England, though their prominence and influence has slowly had to be acknowledged by the aristocracy as economic forces have continually transferred power to them.  In America, old money families have no one above them and are the highest class (with southern landed wealth effectively erased by the Civil War and the Dutch patroonships near New York having failed to produce a lasting, landed aristocracy).  In the U.S. they have historically been concentrated among Northeastern WASPs.  Like aristocrats, they have political power quite disproportionate to their numbers, and they also have great security and ample luxury.  Historically they have looked to the British aristocracy for models of enjoying this luxury, though not without adding significant Yankee inflections.

Augustus Melmotte, The Way We Live Now
Jay Gatsby, The Great Gatsby

3. New money.  Here you find film characters - entrepreneurs, entertainers, surprised heirs, and others - thrust into a new world by new wealth where they are faced with dress (and many other) habits foreign to them and their ancestors.  Newly liberated from anxiety about their financial security, they, for the first time, stumble into the task of playing with luxury on a grand scale in what they might think are aristocratic or old money ways.  Lacking the mindset of the leisure classes, however, they generally continue to utilize and display their wealth according to the values of the working classes, just on a much more expensive scale.  Thus, to those below them on the economic ladder, the clothes and homes of new money can appear incredibly "classy," as they embody working class taste inflated by a massive budget.  To aristocrats and old money, new money can appear quite gaudy and crude.  By contrast, the trappings of old money can appear surprisingly lackluster and dusty to the working classes and to new money yet to be acculturated to the leisure classes.  Also, if they do not learn how to make their money productive rather than seeing it simply as an amount to be spent, their descendants will not become old money, and they are still living with a working class financial mentality.  Similarly, they must learn how to network and utilize the new political power their wealth offers them to really establish their descendants.  They make fascinating literary and cinematic characters as they occupy a difficult position financially above the jealousy and demands of their family and [former] friends and socially below their new financial peers.  Further, if a man from the working class were ever to join the leisure classes, it could only be as new money, making new money the film characters 99% of audience members identify with most in films about the leisure classes.


Income from work is what everyone else has to live from, meaning their income comes from a job.  This is the situation of nearly everyone living in the U.S.  Not only is this income generally much smaller than that of the leisure classes, but many things that are sources of income for the leisure classes are costs for the working classes.  Expenses like rent, insurance payments, and interest on loans and mortgages do not build wealth and often do not offer any returns beyond access and a sense of security.  Their costs are collected as gains by the leisure classes who are invested in - or simply own - the properties, insurance companies, banks, etc.  The leisure classes also do not need to rent because they own, do not need insurance because they can easily pay for unexpected costs, and do not need to pay interest because they can buy outright.  They generally only use such things, if at all, as tools to strategically increase their wealth.  The working classes must use them out of necessity, taking a large bite out of their already smaller incomes.  This leaves them within much greater constraints than the leisure classes, significantly reducing the luxury (including dress options) in their lives.  Unless they are able to live within even tighter constraints to build up savings and investments, their security is only paycheck to paycheck, depending on their health and keeping their jobs.  Their political power lies primarily in their individual right to vote, where they absolutely outnumber the top three classes, though they are quite susceptible to the political narratives created and directed by those very few.  One's income is a much more direct determinant of one's place in the hierarchy of the working classes than it is among the leisure classes.  Still, two working class men could earn the same income but be much more at home in and broadcast the values of two different classes due to their backgrounds.  These are the three working classes I recommend you identify in films:

Roger Thornhill, North by Northwest
Matthew Crawley, Downton Abbey

4. The upper-working class.  These are higher-paid professionals who often gain access to their professions through advanced education (physicians and lawyers being classic stereotypes).  As long as they are employed, they have solid security and moderate luxury.  They have little political power beyond their vote and perhaps some local influence.  This upper-working class (currently about 15% of the U.S. population) is much larger than all of the leisure classes (who combined make up much less than 1%).  They also interact far more with the other working classes than would anyone in the leisure classes.  Thus, to many unaware of the leisure classes, this upper-working class seems to be the "upper" class.  It is quite far from it.  Still, some upper-working class families who have secured high-paying jobs for multiple generations have been able to weave themselves into some of the networks and manners of old money.  Indeed, some call multi-generational members of this class "old money" and new arrivals to it "new money," though I reserve these terms for people who can live off of wealth alone.  Those who are aware of the leisure classes might call this class the "upper-middle" class.

Peter Warne, It Happened One Night
Lt. Frank Bullitt, Bullitt

5. The middle-working class.  These men have little luxury but moderate security - including things like some employer-provided benefits - as long as they are employed.  Their political power is confined mostly to their vote, which is important as they are currently about a third of the population.  They have generally been considered the "middle" class since early in the 20th century.

Philip Pirrip, Great Expectations
Nick Di Angleo, Oxford Blues

6. The lower-working class.  Here we have men who despite working long and hard have scarce luxury and minimal security for it.  Their only political power is their vote, which can be powerful if they use it, as they currently constitute about half of the U.S. population.  This is what many call the "working" class, though of course it is not the only class dependent on work for survival.

As I say in the essay on the development of men's style, for almost all of western history there have really only been two classes and these correspond to the top leisure class (the aristocracy) and the bottom working class.  As I also noted, there have always been a very few bureaucrats/clergy and merchants who lived between the laboring masses and the leisure elite.  This small group of officials and traders exploded during the Industrial Revolution into my middle four classes listed above (old money down to the middle-working class), forming the heterogeneous bourgeoisie or "middle class."  It was not until the 20th century that application of the term "middle class" narrowed to what I call the middle-working class.  Thus, the distinction of the six classes I outline becomes more relevant the closer a film comes to the present, and the use of "middle class" becomes considerably broader the further back in time you move.  In 1780 "middle class" could refer to everything from a modest shop keeper up to an industrialist with more wealth than many aristocrats.

These films are not meant to help you imitate people of higher classes from past ages, but to understand where the current conventions of men's style come from and, thus, what they mean.  This source was invariably the established rich before attention turned to Hollywood and its continuous elevation of new money celebrities from the ranks of the working classes.  The reason the leisure classes are so disproportionately represented in my list of films up until the age of Hollywood is because they have decided what you may wear today.  Here you can learn not only what looks have filtered down to you over time, but you can learn their meaning in order to combine them intelligently and deploy them appropriately in your own style.

And certainly if part of your motivation for learning to dress better is to navigate new or higher social spheres to any degree, it is best to know what you are doing so that the style you develop serves you more than it limits you.  As you move beyond the style of your adolescence, you are most likely playing with the codes of class, even if only within the working classes.  And rest assured that there are still layers of codes just within the working classes.  These films can help you learn how to use clothes well in class interactions, and how to take it too far, even on a much more modest and subtle scale, from observing characters and their choices. Films offer illustrations of when dress signals are used wisely and serve and when they are botched and do damage.  They can help you formulate your strategy of how to proceed with both caution and confidence.


Now that we have taken a closer look at class and how to think about it in relation to men's style in films, let us move on to some of the other elements you should pay attention to in your viewing to really understand the history of men's style.

Prof. Henry Higgins dressed for
the evening in  Pygmalion

TIME OF DAY.  The higher the class of a character, the more likely there will be a marked difference between daytime and evening clothes, especially further back in history.  Some characters regularly wear different morning, afternoon and evening clothes plus all additional occasional outfits (for shooting, riding, etc.).  Pay close attention especially to how the rich differentiate between day and evening dress and how this may or may not translate down to men of lower classes.

LOCATION.  Look for a difference between "country" and "town" clothing, a British distinction denoting either what one wears at one's country house or what one wears for business and society in London.  This is the most important locational distinction in men's style.  It can influence the difference, say, between what a man would wear in the small town in Connecticut where he lives and what he would wear to work in Manhattan.  Pay attention to how locations call for specific choices.  Observe these changes and think about what they achieve and mean.

EVENT.  What does a character wear to a party?  What time of year is the party?  Indoor or out?  Day or evening?  What kind of party - what is its purpose?  Who else is attending?  What about to a sporting event?  To a wedding, funeral, state ceremony ... ?

WEATHER and SEASON.  How does the character dress for heat, cold, rain, snow, etc?  How do color palettes, materials, and combinations change throughout the year?  Pay attention to cold-weather layers like outer coats, hats, scarves, etc.  These vary according to class as does the clothing worn at a place like the beach.

Robert Crawley, The Earl of Grantham, dressed for an
out-door, summer party in the country on Downton Abbey

~You will notice that generally the higher the class of a character is, the more specific his clothing is for all the variables of occasion.  This fluid specificity is a strong class marker because 1) wealth allows for a larger wardrobe, 2) the leisure classes have less to do out of necessity than the working classes and thus have more time and energy to spend on nonessential concerns, and 3) it separates them from the rest.  Such men traditionally have/had valets who help them keep track of and navigate all of their options correctly.  If your idea of improving your style means subtly harnessing the power of class signals, and to avoid damaging faux pas you must at least understand them, you want to learn what it means to dress for occasion, even if not to the extent of an Edwardian lord.~

FORMALITY.  As you pay attention to all of the specifics of occasion, develop a feel for how they determine the formality the occasion requires.  Formality is the most critical aspect of dress one needs to understand to be at home in a situation and avoid missteps.  Observing formality does not make you look good as much as it makes you look right.  You can get a brief introduction to the scale of formality still applicable in the West here.

AGE.  Older characters often wear styles or retain certain elements from earlier periods while younger characters wear the newest looks for their time.  Pay attention to this and consider the idea of age appropriate dress, figuring out the balance that works best for you at your age and in your social environments.  Similar to this is the retention of older, more conservative - possibly even archaic - styles in more formal settings.  With each character ask yourself how the conservative v. trendy nature of his clothing for any given occasion reflects his power and position and the formality of the occasion.

RECYCLING.  As you move through the history of men's style, you will see many things recycled from earlier periods.  What is the message the renewed detail, garment, and/or ensemble sends in its new context?  What kind of historical meaning is the wearer tapping into or playing with?  Paying attention to how this has worked for centuries will help you know how you may want to recycle older items and looks in your own style.  It is almost never a good idea to recycle an older look in every detail - it ends up looking like a costume.  Pay attention to how older looks inspire new ones and how to take inspiration without playing dress-up.

James Bond, Casino Royale

CHARACTER.  This is where personality comes in.  Beyond all of the elements of class and occasion is the individuality of the wearer.  Examine characters with specific traits you admire.  How are these traits expressed in details, items or ensembles they wear?  Do they have sartorial habits (a certain color palette, accessories, etc.) that express these traits?  If the costuming is well done, they will.


How the Films were Selected

The films I list focus on classic Anglo-American tailored menswear within contexts that highlight class structure and interactions, primarily in the 19th and 20th centuries.  One could also profit from a historical study of uniforms in war films, or of cowboy/ western style, of adventure/ safari/ colonial style, artist style, rebel style, working class style, futuristic/ extra-historical style, period fads, etc.  Let me know if you compile any such chronological list of films, and I may offer a link to it.

For my list I have tried to fulfill as many of the following criteria as possible:

• the clothing is accurately typical for the period
• multiple classes and occasions are demonstrated as accurately as possible
• the costumes are well designed, selected and tailored
• the movie itself is enjoyable to watch

For all periods, I try to offer a variety that, if you watch all of them, you will see the style of the period expressed for most classes, in quite a few different occasions (times of day, seasons, town and country, etc.), and on a large range of personalities and characters.  I am afraid many of the films fail in at least one of my criteria, and one could watch these only with an eye to spotting inaccuracies.  Please feel free to do so.  I have collected them in order to provide the conscious viewer with a detailed and dynamic study of the history of men's style.

Sir Richard with Lord and Lady Grantham, Downton Abbey

As you will notice, some of the films are not "films" at all, but well-done TV series.  These show you many more changes of outfit than you would get in the more limited time of a feature film, and they are able to develop a deeper relationship between the character, his world, and his style.  They are also more subtle, detailed studies in class relations. TV series based on literary works, like those of Austen, Gaskell, Wodehouse, and others, are a fantastic resource for the man wanting to understand the history of what he may choose to wear.

I assume you are capable of using websites like IMDB to learn about films and and to use YouTube to watch trailers or available clips to decide which films you want to see.  Rotten Tomatoes may also guide you in your selections, and Wikipedia often offers plot summaries.  If you are offended or bored by certain kinds of material or themes, I trust you will be able to determine if a film recommended here contains such material or not before viewing it.  If you do not have the attention span for films made twenty or more years ago, I suggest you learn to enjoy films of a slower pace as there are so many gems in earlier decades worth viewing.

Once we reach the 1920s we can rely less on recreations and view films actually made in the time they represent.  This ensures an accuracy harder to secure with costume dramas.  Also, in the early decades of Hollywood, stars selected and assembled their own wardrobes for films, one of the reasons Cary Grant, Fred Astaire, Jimmy Stewart, Gary Cooper and others are such style icons in a way today's professionally styled actors are not.  The trade-off is that these films are often not in color, losing a critical element of dress.  Still, many of the films of these stars had a serious effect* on the men's style of their periods and of the history that followed.


Final Note on Where to Begin

Before and after: Louis XIV, The Taking of Power by Louis XIV

I offer at the beginning of the list a film on the 17th century.  It was under Louis XIV that western men's style took off into one of its most extravagant expressions in history.  The two pictures to the right, taken from the film I suggest, show how he changed European fashion from a plainer style still rather similar to that worn by the American pilgrims to the explosion of pomp and complexity that characterized everything at Versailles.  The new look he instituted included wigs, all kinds of lace and ribbons, silk stockings, pumps with yet more ribbons on them (those beribboned man-pumps are still around, you know), and eventually even makeup.

Though few today may find this look practical - let alone appealing - what is instructive is how Louis used it to consolidate his power and control his entire kingdom.  Controlling a kingdom through your style choices while setting the style for all of the West - that is style power.  Louis XIV was one of the most powerful men in history who knew exactly how to use clothes to his advantage, and he is one of those few men in history whose personal style choices dramatically changed the standards for all other men.  He offers a lot to learn.  (At the very least, this short clip will let you into some of Louis' style-thinking).  Throughout the 18th century, men's style continually toned its extravagance back down.  The films I offer for this century show where men's style was before the French Revolution and Beau Brummell changed things forever around the year 1800.

It is really with the Revolution and Brummell that the story you need to know best really gets going.  Beau Brummell: This Charming Man (2006) may be where you want to begin.  Even though it is my least favorite recommendation on this list (I have never even been able to finish watching it), it has some value and the costumes are done well enough.  Besides presenting a dramatization of Brummell, the film's first 25 minutes or so graphically (if not cartoonishly) demonstrate the shift from what was left of the baroque style instituted by Louis XIV to the much more austere and familiar men's style of the 19th and 20th centuries.  Pride and Prejudice is a far better production, and Mr. Darcy presents a better model of manhood than Mr. Brummell anyway.  Perhaps after viewing the beginning of Beau Brummell, you may want to move on to Pride and Prejudice.  (Once Brummell's circle have all been dandified and we get our first introduction to Byron, the movie becomes much less useful and even more tedious.)

In truth, the period that featured the most looks that are still viable in tailored menswear today is the 1920s through the 1960s - the period for which I offer the most suggestions.  You may just want to watch films covering these years, though, if you want to understand why men are wearing what they wear starting in the 1920s, you will need to go back and begin with Beau Brummell and Mr. Darcy.  If you want to know why the dress of these two was so radical and had such a lasting impact on our standards, you should go back to Louis XIV.

Click here to return to my list of films.

Enjoy!


_____________
* The unfortunately short-lived Men's Vogue produced in 2008 a list of the 50 films most influential on men's style.  This chronologically ordered list would certainly be worth watching in addition to my list above, though with a different focus in mind (to see how film influences style, not necessarily to see the development of the history of style by means of film).  The two lists do recommend some of the same films, and I have underlined those films below:
1. It Happened One Night (1934)
2. Sullivan’s Travels (1941)
3. Casablanca (1942)
4. An American In Paris (1951)
5. Roman Holiday (1953)
6. Rebel Without A Cause (1955)
7. To Catch A Thief (1955)
8. L’Avventura (1960)
9. Plein Soliel (1960)
10. La Notte (1961)
11. Last Year at Marienbad (1961)
12. The Misfits (1961)
13. Lawrence of Arabia (1962)
14. Alfie (1966)
15. Endless Summer (1966)
16. The Graduate (1967)
17. Bonnie & Clyde (1967)
18. Guess Who’s Coming to Dinner (1967)
19. 2001: A Space Odyssey (1968)
20. The Thomas Crown Affair (1968)
21. Easy Rider (1969)
22. Midnight Cowboy (1969)
23. On Her Majesty’s Secret Service (1969)
24. MASH (1970)
25. Klute (1971)
26. Play Misty for Me (1971)
27. The Discreet Charm of the Bourgeoisie (1972)
28. Shampoo (1975)
29. The Man Who Fell to Earth (1976)
30. Saturday Night Fever (1977)
31. The Deer Hunter (1978)
32. Hair (1979)
33. Mad Max (1979)
34. American Gigolo (1980)
35. Chariots of Fire (1981)
36. Blade Runner (1982)
37. Out of Africa (1985)
38. Full Metal Jacket (1987)
39. Wall Street (1987)
40. Bull Durham (1988)
41. Reservoir Dogs (1992)
42. Singles (1992)
43. Trainspotting (1996)
44. The Matrix (1999)
45. Royal Tenenbaums (2001)
46. Dogtown and Z Boys (2002)
47. 2046 (2004)
48. American Gangster (2007)
49. I Am Legend (2007)
50. Michael Clayton (2007)