A style of men’s clothing that will never go out of style and why I think that’s cool.

I’m obsessed with things that can last a long time.

I think its because things today change so quickly and that makes me anxious.

I get a thousand notifications a day. I’m having 20 conversations on phone at once. And social media moves so damn fast.

Plus, I’ve personally moved often and have had lots of different jobs. A lot of change.

And so, because I have so much change in my life, I’ve grown to love consistency and things that can, and have, lasted a long time.

In particular, my current interest is on men’s clothes and how clothing has intertwined with my other favorite hobby: American history.

This has led me to ask myself: What clothing was cool in the past, is still cool now, and will likely be cool in the future?

Well, after reading a dozen books, listening to hours of podcasts, and researching like a madman…I can confidentially answer that question: Ivy Style.

Old Money will always be cool.

The suit was invented in England. Crisp, sophisticated. A man wearing a beret and smoking a cigarette couldn’t be more stereotypically French. Artsy, slightly smug.

These outfits say something about a country’s culture. That interests me.

But what about America? What’s our quintessential style and what does it say about us?

The answer is Ivy Style. Its as American as it gets. But unless you’re a frequent poster on StyleForum, you’ve likely have not heard of it. But it’s American’s greatest contribution to fashion and in my opinion, cool as hell.

Most of my readers on this blog are internet nerds who don’t care about fashion.

They’re the t-shirt and hoodie type. I get that.

But by the end of this post, I hope to inspire you to explore Ivy Style. But at the very least, I hope you enjoy learning about something that you see everyday but likely don’t know the backstory.

Something magical started to take place after WW2

In the 1940s and 50s, after WW2, millions of American men came home.

To reward their heroism, the government set up dozens of ways for them to get ahead: discounted mortgages, job training, and healthcare perks.

This made the economy thrive. There were now millions of young families who had great jobs, owned homes and for the first time ever: had time and money.

And what does a young guy do with time and money? They leisure. That’s right. “Leisure.”

You see, prior to WW2, the idea of leisure, or to play golf, travel, and explore hobbies, was an idea reserved for the rich. The decedents of tycoons from the Gilded Age who didn’t have to work, they had leisure time, not middle class folks. But that changed in the 50’s with the booming economy.

In fact, it was during this era that America’s middle class was formed. A middle class family could afford a home on just dad’s salary and now they had time to be with the family after work and had disposable income.

So these young and thriving Americans got into all sorts of new hobbies. Hiking, being outside, sports.

And along with their new hobbies, money, and time, these young men wanted to look good. They needed clothes to go along with their new lifestyles.

Meanwhile, Ivy Leaguer students were dressing like British aristocrats

Up until in the 1940’s, American men’s style can be described in one word: grey.

The grey three piece suit, a starched white shirt, and a dark die. That was peak status. It screamed the important values of the day: Conformity. Rigidity. Order. The perfect uniform for a man committed to the corporate grind.

But in mid 1900’s there was a group of people who wanted to both climb the ladder but also rebel against the what the grey suit stood for. Those renegades were Ivy League students.

Students at universities like Harvard and Yale dressed like British aristocrats. Heavy, tweed jackets. Tennis sweaters. Double breast blazers. Standard garments for the British aristocrat uniform.

In Status and Culture, W. David Marx examined why Ivy League students in the 1940s adopted British aristocratic fashion.

The answer is simple: they wanted to project a sense of effortless belonging and subtle confidence.

“Ivy League students in the 1940s adopted the style of British aristocrats not merely for its elegance,” Marx writes, “but for what it signified: a quiet confidence, a disdain for overt displays of wealth, and a sense of belonging to an exclusive social class. The soft shoulders, natural fabrics, and relaxed tailoring conveyed a subtle message: one didn’t need to try too hard when one already belonged.”

In fact, at the time, one of the most popular dressers of the day was Edward VIII, better known as the Duke of Windsor. Casual tailoring, vibrant colors, Prince of Wales checked suits. These were popularized by the Duke.

And the Ivy League students, aspiring to be elite like their aristocratic British ancestors, ate it up!

Soon, this idea spread to universities across the country. It wasn’t just the east coast elite student, though. that is where most of the influence came from. Students everywhere were adopting the old money, British look.

WW2 Veterans Meet Old Money

Now back to our WW2 veterans. You see, thanks to the GI Bill of 1944, millions of veterans were now able to afford college. And what happens when you mix an aristocrat, old money aesthetic with practical minded ex-soldiers eager to leave behind the formality of military life?

That’s what we now call Ivy Style.

The veteran’s style (along with their children’s future influence) was all about practically. Paired with the traditional British look that students around the country came to love, a new type of style was created.

Stylish but not restrictive. Sharp, but still casual.

Sport coats with natural shoulders. Pre-Ivy suits were boxy and militaristic with padded shoulders, emphasizing formality over comfort.

Flat-front trousers with slim cuts. Trousers previously were high-waisted and wide-legged, designed purely for formal occasions, unlike Ivy’s tailored chinos or wool pants with casual cuffs.

Crewneck sweaters (previously worn for warmth, not style), brown penny loafers (vs black leather oxfords), and the oxford cloth button-down shirt (traditional dress shirts were stiff and formal). Chinos and khakis (previously only worn in the military).

These were all creations that came from Ivy Style.

A lot of the brands that we love today came from Ivy League

Ivy Style thrived in the 50’s and 60’s. Brands that you and I know of and love today…this is the time when they were created or popularized.

Brook’s Brothers, the godfather of Ivy and the inventor of the oxford button down collar shirt, was at the height of their influence. John Kennedy, the poster child of Ivy Style, was famous for wearing Brook’s suits.

And then in 1967, a 28 year old Brooks Brothers clerk decided to go off on his own. His goal was to take the foundations of Ivy (the preppy, collegiate look with its roots in the elite Northeastern universities) and elevate it, blending it with elements of Old Hollywood glamour, aristocratic British style, and his own aspirational vision of the American Dream.

He named his brand after himself: Ralph Lauren.

But Japan did Ivy better than anyone

Like they’ve done with cars and electronics, along came the Japanese and they did Ivy, an American invention, better than anyone.

Post WW2, Japan was going through its own changes. After the war, America occupied Japan.

The Japanese expected the worst. In his book Ametora: How Japan Saved American Fashion, author David Marx said that the Japanese expected the occupying American’s to “rape and kill and burn everybody with flamethrowers.”

This fear, however, was unfounded.

The American’s took the opposite approach. They were generally kind and the Japanese and American soldiers had great rapport, a directive from US President Truman, who hoped being kind would build a better relationship with Japan.

“Instead of punishment, the Americans brought democracy, baseball, and chocolate,” Marx said, fostering an unexpected rapport between occupiers and the Japanese people.

During this time, Japanese teenagers, living in a Japan that was questioning what it stood for and starting anew, wanted to rebel against the traditional Japanese values of isolation and, well, general uptightedness (not a real word, I think).

And so they were open to being influenced by their American occupiers and American culture. The Americans were well fed and large in size. They were happy and free. To many Japanese teenagers, America represented hope, civility, vitality and freedom.

This is when Kensuke Ishizu, a young entrepreneur, pounced.

Ishizu was obsessed with American values. Expression, casualness, freedom. He also loved American fashion, particularly Ivy Style. The tweed jackets, blue jeans, khakis, oxford button downs. He loved the flair and the individualism that these clothes represented.

Attributes that the down and beaten Japanese desperately craved.

And so, he brought those styles to Japan by founding his clothing company, VAN Jacket. Along with his clothing company, he helped to create and inspire, loads of Japanese magazines that explain what Ivy Style was and the rules of it.

Ishizu’s was incredibly influential, and not just in Japan. He meticulously dictated and documented how the American’s dressed and codified Ivy Style.

The right way to wear a tie (four in the hand knot!), navy blazers with gold buttons as the standard, avoiding logos. Things that we look at today as “standard”, Ishizu was the one who first wrote those things down.

An interesting fact: Uniqlo is one of the largest clothing company’s in the world with a $100b market cap. Tadashi Yanai, the founder of Uniqlo, father worked for VAN Jacket. Yanai explained that VAN Jacket and Ishizu undoubtedly shaped his own approach to apparel retail.

My Take

I’ve had a bunch of buds tease me for my obsession with menswear.

Why do you care about this, Sam?

Well, I’ll tell you:

I think in a world where things change so fast, finding things that are timeless is comfortable and romantic. Not to mention just flat out practical.

I also think that young men today, in most cases, don’t have a rite of passage. When does a boy become a man? There’s not a clear threshold. Which means often traditions aren’t explicitly discussed. This ranges from what to wear but also how to treat people, how to shake hands, that sort of stuff.

And because of that, its easy for boys to stay boys and never grow up. Which means a lot of sloppy, poorly dressed men.

But when some men do become interested in dressing better, there’s not many places to turn to.

They don’t know the rules because the traditions haven’t been passed down. And often, they’ll be called gay or feminine for caring about how they look (which is bullshit, by the way. For centuries, the most masculine men most certainly care about appearances).

And I think that bums me out. So, I want to find a solution.

And finally…I’m a history nut. And clothing is a very practical way to feel and touch history, to be in tune with how things used to be done.

NOTE: There are so many different styles and aesthetic that I like and think are cool. You should do what you think is great. Dress is a social language. So decide what you want to say, learn the language, and go out and say it.

If you’re interested in this topic

When I find a topic that I like, I like to read, watch, and listen everything on it. I then write an essay my thoughts to I internalize my learnings (that’s this post). Here’s a list of some of the things I consumed. If this post interested you, check out these things.

• Dieworkwear (blog and twitter): Derek’s twitter handle breaks down the history of menswear. His blog is every better. Currently, I think he’s the best, most insightful writer on this topic.
• Permanent Style (blog): Simon Crompton’s blog on mens tailoring. He does a great job of reviewing different clothes and explaining the rules.
• Put This On (blog): Jesse Thorn’s blog is like the everyman’s guide to dressing better. It’s accessible, witty, and packed with practical advice.
• Take Ivy (book): A hotographic love letter to Ivy League style in the 1960s. A cult classic.
• Black Ivy (book): My favorite of all these. Its a coffee stable style book. Easy read, inspiring stories. The photos are breathtaking. About how black Americans put their flavor on Ivy.
• Alan Flusser’s Books: Dressing the Man, Style and the Man, and Clothes and the Man. Flusser’s books are incredibly comprehensive. Start with Dressing the Man: Mastering the Art of Permanent Fashion.
• Very Ralph (documentary): An HBO documentary on Ralph Lauren’s life, style, and influence. Fun and can watch with anyone, not just people who wanna learn about this stuff.
• Ralph Lauren Books: Ralph Lauren by Ralph Lauren and Ralph Lauren: In His Own Fashion by Alan Flusser. Beautifully crafted books on Ralph’s timeless influence on fashion and defining American style.
• Brooks Brothers: Generations of Style (book): Brooks Brothers may have had the single greatest influence on American menswear. They’re a 200 year old company, which is insane. If you want to understand the roots of American style, start here.
• Ametora: How Japan Saved American Style (book): After WWII, Japan adopted American fashion but added their own flair. This book tells the story that story.
• Status and Culture: How Our Desire for Social Rank Creates Taste, Identity, Art, Fashion, and Constant Change (book): David Marx breaks down how status shapes everything. From what we wear to how we define ourselves. A deep dive into the psychology behind trends, taste, and why certain styles gain or lose popularity.
  

A few of my favorite Ivy photos