Watching Old Movies Will Make You A Better Dresser

My goal with this article is get you guys interested in old movies because watching old movies will help make you a better dresser!

Collider.com featured a very good article recently about ten classic movies for beginners. Basically, if you had to show someone who wasn’t familiar with the Golden Age of Cinema ten movies, those are the movies you should start with.

And, honestly, their list is solid and you should definitely read it!

It got me thinking about my own love for classic movies and how that intersects with my love of classic menswear. In short, watching those old movies has helped me nail down my own style because they gave me tons of examples of how to wear things like suits, ties, hats, and pocket squares with ease.

Nowadays, in our increasingly casual world, we don’t have too many of those examples left, so looking to old movies is a great source of inspiration.

I always like to introduce people to some of my favorite old movies and I would like to do that here, since I feel that a love for classic cinema can help you along your sartorial journey.

One of the things that keeps people from exploring old movies is the belief that those movies are much more boring than anything modern. Many people look at anything black-and-white and scoff at it, thinking that it can’t possibly hold their attention for two hours. Those same people usually have the same feeling about classic literature.

Granted, if the only things that can keep your attention are special effects and super heroes, then you’re right; these movies will not interest you. But don’t think that just because these movies are old that they can’t keep you glued to your seat. All the movies in this article are awesome, if you’re willing to give them a chance. I have purposely included a wide range of genres so that there is something for everyone.

Many of the movies on this list feature awesome traditional menswear, but that’s not the sole reason they are included; they’re just good movies. Where applicable, I have pointed out any notable outfits, but not every movie features something special, style-wise. However, once you get comfortable watching old movies, you’ll probably watch more of them and THAT’S how it will start to improve your understanding of menswear.

I have purposely left off a few movies that were featured in the Collider article, like Casablanca, It’s A Wonderful Life, and The Philadelphia Story. Those are some of my favorite movies, but I don’t want to waste your time with duplications.

In no particular order…

#1 – Roman Holiday

This is the movie that made Audrey Hepburn a star and earned her an Oscar. The plot revolves around Hepburn’s unsuspecting Princess Ann running around Rome with Gregory Peck’s Joe Bradley, a newsman determined to get the ultimate scoop. Hijinks ensue and the two fall in love.

It’s a simple and silly plot, but what makes this movie so magical is the chemistry between Hepburn, Peck, and Peck’s artist best friend, Irving, played by the excellent Eddie Albert.

I wrote an article some time ago about Albert’s killer wardrobe in the film. Honestly, you’d be hard-pressed to find a more stylish cinematic trio than Hepburn, Peck, and Albert.

Roman Holiday is probably one of the top three romantic comedies of all time. If you’re looking for a stellar date-night movie, this one is it.

#2 – 12 Angry Men

The first time I saw this movie, I was about twelve years old. I stumbled upon it while flipping channels one day and I was immediately drawn in. This was YEARS before I ever began enjoying old movies. It was so good that I, even at twelve, couldn’t pull myself away from it. I HAD to see what happened!

You’re probably familiar with the plot. Twelve jurors sit down to deliberate on a murder case that seems open-and-shut. They all vote guilty straight away, with the exception of one man who feels it is their duty to, at the very least, talk things through before they render their verdict.

Ostensibly, this is Henry Fonda’s picture, and he is his usual first-rate self, but there are so many good performances (roughly eleven others), specifically the fiery Lee J. Cobb as the juror most determined to send the young suspect to the chair.

While 95% of this film takes place in one room, it never feels “gimmicky” like some other movies made around the same time did. And even though the vast majority of the “action” is a bunch of dudes (wearing almost identical white shirts and dark ties) sitting around a table talking, the movie hurtles along at such a clip that there is absolutely no wasted space.

This is a tight, exciting, endlessly watchable movie. It’s the kind of movie that even if you caught it in the middle at midnight, you’d still sit through the rest, regardless of how many times you’ve seen it.

#3 – Dial M For Murder

The Collider article mentioned Rear Window, which I cannot argue with. It’s a great movie anchored by great performances by Jimmy Stewart and Grace Kelly. However, I submit Dial M For Murder as the best Alfred Hitchcock movie to show someone who isn’t really into old movies.

I’m not a huge Hitchcock fan. I like plenty of his movies, but mostly because of the stars he chose to be in them. I love Jimmy Stewart so I’ll happily watch Rear Window or Vertigo. I love Cary Grant, so I enjoyed North By Northwest and Suspicion. But I usually find that I like Hitchcock’s movies DESPITE them being Hitchcock movies, not because they’re Hitchcock movies. That’s because I always have some major gripe about them, which I’ll probably go into in another article.

The two best Hitchcock movies, in my opinion, are Psycho and Dial M For Murder. For the purposes of this article, I didn’t include Psycho since it’s more of a horror movie and everyone knows about it already. Dial M For Murder is a bit less well-known for people who aren’t already into old movies.

The movie, like 12 Angry Men, takes place mostly in one place: the apartment of a retired tennis star who is plotting to murder his cheating wife. He thinks he has created the perfect plan, only the would-be-murderer bungles the job and actually gets himself murdered by his mark (played by Grace Kelly). The scheming husband, played by Ray Milland, then attempts to pin the whole crime on Kelly.

This is another talk-heavy film and, upon the first viewing, required many pauses of the DVD and questions to my wife in order to straighten out what was actually going on. My wife actually thought that I DIDN’T like the movie because I was having a hard time following it at first. The great thing about that, is that the movie is so enjoyable on repeated viewings since everything falls into place much more easily.

This film is one that I think has some of the best menswear of any movie. There are four main male characters: Milland as the villainous husband, Anthony Dawson as the hapless hitman, Robert Cummings as the “other man”, and the inimitable John Williams as the policeman who unravels the case.

Milland and Cummings give us the full-cut suits, tuxedos, and crisp white shirts, Dawson the more casual sportswear, and Williams the sublime, double-breasted, pinstripe, flannel suit and homburg.

If you’re into classic menswear, you’ll think “damn” every time any one of those guys walks into the shot.

You’ll probably think that about Grace Kelly, too.

#4 – Gone With The Wind

Ok, hear me out on this one…

Literally everyone has heard of this movie. The reason why I am including it is because not many people really understand how watchable this movie is. Yes, it’s about four hours long. Yes, it’s jam-packed with problematic elements including, but not limited to, domestic violence, rape, and the literal owning of people.

But the movie is still a very good movie and very easy to watch, provided you split it up over two nights. That’s what my wife and I do and it makes it very manageable. Despite being a four-hour movie, the plot hums along and doesn’t really ever sag. You’re not going be bored, I promise you!

Here is another thing to keep in mind while watching this movie: most people misunderstand it. What I mean by that, is that most people either LOVE the fact that the movie lionizes the south during the Civil War, or they HATE the film for that exact reason. Here is what both sides of that argument miss…

Everyone in the movie is a loser. They are so obviously losers! They are clearly portrayed as almost wholly detestable and I feel that that goes over most people’s heads.

Ok, I know they’re all Confederates so they’re losers by definition, but it goes further than that. Let’s look at some of the major characters, shall we?

Scarlett – Treats everyone like shit. Pines over the married Ashley. Marries about a dozen men she doesn’t love.

Rhett – All-around cad who leaves a carriageful of vulnerable women (and a baby!) in the middle of the road so he can go off and fight in a war he doesn’t care about that’s already all but lost. Honestly, Rhett could have used his famous “I don’t give a damn” line right then considering he just ran away and left the women to fend for themselves.

Rhett runs off to join “the cause” right after the burning of Atlanta. Want to know when that happened? November of 1864. When did the south surrender? April of 1865! Rhett joins the war right as it ends. He tries to pass it off as heroically fighting the unbeatable foe, like some treasonous Don Quixote. But it just comes off as a stupid, selfish decision. He then immediately gets captured.

Once he wraps up his spectacular failure of a military career, he comes home and rapes his wife. But that’s not all! He also hits her and kinda-sorta-accidentally-on-purpose knocks her down the stairs causing her to miscarry.

Oh, but Clark Gable is just so watchable!

Ashley – Ah, the biggest loser of them all! I think Ashley is one of the most hated characters in cinematic history and he isn’t even supposed to be a bad guy! He’s just so irritating and whiney. He says he loves Scarlett but is married to Mellie (his cousin!) for the entirety of the movie. The only thing Ashley does well is deliver weepy soliloquies.

The only good characters in the movie are Mellie, who is just nice to everyone, Mammy, because she constantly tells everyone how stupid they are, and that hooker who is friends with Rhett.

With all that being said, when you watch Gone With The Wind it is obvious why this was the highest grossing movie for like 80 years. It is a grand spectacle and is best viewed on a big television, if only for the riveting Atlanta scene alone.

Despite most of the characters’ all-around awfulness, the performances of Vivian Leigh as Scarlett, Gable as Rhett, Hattie McDaniel as Mammy, and Olivia de Havilland as Mellie are absolutely iconic.

Pour yourself a few drinks, keep in mind that everyone in the movie sucks, turn up the volume, relax and enjoy a very well-done (if very long) movie.

#5 – Harvey

Of all the movies on this list, I would call this one a perfect “gem”.

Harvey tells the tale of a man named Elwood whose best friend is an invisible, 6-foot, 3-and-a-half-inch rabbit named Harvey. Elwood’s sister and niece have lost their patience with Elwood, since everyone in town thinks he is a kook, and try to have him committed to a mental hospital.

One might think that the bit of having Jimmy Stewart interact with nothing for the whole movie would get tiresome. However, this movie is so much deeper than the initial sight gag of having Elwood constantly introduce people to an invisible rabbit.

This movie is really about how we treat each other and how we treat those who don’t fit society’s mold. Is it really so bad that Elwood is friends with Harvey when Elwood is probably the nicest guy in town?

Towards the end of the movie, Chumley, the head of the mental hospital, convinced Elwood is telling the truth about Harvey, discusses with Elwood the extent of Harvey’s magical powers. Elwood tells Chumley that Harvey has the ability to whisk you away to anywhere you want to go for as long as you want. Chumley asks where Elwood would go if he could go anywhere in the world. Elwood tells him that there isn’t anywhere else he would like to be than right there with whomever he is with at the moment.

That’s the root of Elwood’s appeal. He makes everyone around him feel as though they are the most special person in the entire world. Everyone falls in love with him.

Whenever I watch the movie, I’m always struck by how ACHIEVABLE Elwood’s level of charm is. He doesn’t do anything extraordinary. But he listens when people talk. He remembers everyone’s names. He takes an interest in their interests. He is liberal with his compliments. He introduces people to each other.  

Elwood is love, humanity, curtesy, and grace personified. So what if he talks to an invisible rabbit! Is his belief in Harvey actually harming anyone? Does Elwood’s belief in Harvey somehow negate all the good things about him?

What are the things that matter most to us, as a society? Is it that someone adhere to our rigid standards of how they should act? Is that what we value most? Or is it having someone who tells a young woman they’re beautiful when the object of that woman’s affection is too blind to see it?

The other characters in the movie don’t really deserve Elwood, just like we didn’t deserve someone like Fred Rogers. At the climax of the film, the rest of the characters are forced to confront the reality of Elwood being “normal”, what that means for them, and if that’s really what they wanted all along.

This is a sweet, light, feel-good movie.

#6 – The Man Who Shot Liberty Valance

Jimmy Stewart makes his second appearance on this list alongside western stalwart and all-around caricature of masculinity, John Wayne.

Now, I am not normally a western movie fan. Yes, I liked Treasure of the Sierra Madre but that’s about it. Even if you don’t normally like westerns you should definitely give this movie a try.

Stewart plays an idealistic attorney grappling with the reality of a world where might makes right. Wayne plays the tough cowboy trying to talk some sense to Stewart before he gets blown away by Lee Marvin’s ruthless outlaw, Valance.

Stewart is his usual dependable self as a man with integrity fighting against a Darwinistic, dog-eat-dog world (Mr. Smith with a bigger hat, if you will). But it’s really Wayne who steals the show with a sensitive, stoic (and ultimately tragic) performance.

This film isn’t just popcorn fare. It will definitely get you thinking, specifically about the title and whom exactly it’s referring to.

#7 – Gaslight

Yes, this is where the phrase “to gaslight” comes from.

The luminous Ingrid Bergman plays a young bride who is driven to madness by her scheming husband. He slowly convinces her she is crazy in order to gain access to her family’s possessions.

This is a movie I like more and more every time I watch it. What’s so frightening about this film isn’t so much that the husband convinces his wife she is nuts, but the fact that he so easily convinces everyone else that his wife is nuts!

He does it so subtly, at first, peppering their casual conversations with comments about how she is forgetful. These comments lay the groundwork for more serious accusations down the road that Bergman’s character is too doubtful and confused to refute.

Again, the terrifying thing is how deftly he convinces everyone in their sphere that his wife really is crazy, ensuring she has no one to turn to.

This is a movie that makes you want to shout at the screen, which makes the climactic confrontation between husband and wife that much more cathartic.

#8 – It Happened One Night

Here is Clark Gable again in a much less problematic role.

Gable plays a newsman (naturally) who crosses paths with Claudette Colbert’s spoiled heiress as she flees her controlling father, in order to marry the man of her dreams (or so she thinks).

The reason I initially watched this movie was because I read an online article about the suit Gable wears in the film. I am not going to try to rehash the points from that article because, honestly, that article is the best example of menswear writing I have ever read and I would not be able to improve upon it. Please do yourself a favor and read that article.

The movie itself is a joyful romp due to the chemistry between Gable and Colbert. It’s silly and light and, just like Roman Holiday, is a perfect date-night flick.

So, off the top of my head those are the eight films to serve as an appetizer for classic movies. Like I said, not all those movies have stellar menswear, but becoming a fan of old movies will make you a better dresser simply because you’ll be exposed to how classic menswear should be worn.

That all being said, there are a handful of old movies that tend to garner a lot of praise that I think you should stay away from if you’re not really into classic cinema yet.

My wife and I watched Citizen Kane not that long ago. It popped up on TCM and I was like “We HAVE to give it a try!”

Honestly, I can see what all the fuss is about, but it’s NOT a great movie to watch if you’re not a film snob. Yes, Orson Welles gives a great performance (outdone, in my opinion, by Joseph Cotten), and the camera techniques are interesting, as is the general “mood” of the film, but beyond all of that, it’s not all that interesting. It’s the tale of the rise and fall of a rich, hubristic dude. It is interesting seeing the whole “Rosebud” sequence, but other than that, I found myself growing a bit bored with it.

Another classic film that fell a little flat for me was The Wild One with Marlon Brando. Yes, it’s cool seeing Brando in his Schott Perfecto, but beyond that, it’s just seventy minutes of obnoxious extras in leather jackets drinking beer and smashing windows. Brando doesn’t even really do much of anything in the film except wander around town and stare at the local pretty girl. If you’re looking for the raw, sweaty explosions of Brando’s Stanley Kowalski, you’re going to be waiting in vain.

Let me know what you think of this list and if I forgot any that you think deserve to be mentioned!

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