For our latest Battle of the Wits giveaway, Sperry Top-Sider has generously donated four pairs of the new 75th anniversary edition of its classic Canvas Vulcanized Oxford sneaker. It even comes in a cool replica of the original 1935 box.

The shoe, priced at $75, comes in your choice of white, navy or Nantucket Red.

In the spirit of the CVO’s nautical heritage, here’s the question:

You’ve got a fresh pair of Sperrys, and your custom yacht with the walls lined in blue oxford cloth is ready to set sail anywhere in the world. Where do you go, and why?

Use the leave-comment feature to regale us with your inspiring and creative trip to the ends of the Earth, in 25 words or less.

The usual honor-code rules apply: One entry per household, US residents only. Contest closes Wednesday at 5 PM Eastern Standard Time. Bon voyage.

The designers at Gant Rugger appear to have hit the books in preparation for the Spring 2010 collection. Or at least one book: “Take Ivy,” the 1965 Japanese photo book hyped to the max on the Web the past couple of years.

The sartorial motifs of “Take Ivy” abound in the Rugger collection, mixed and matched with colors changed. There are hooded rain slickers, shorts worn with white socks and loafers, skinny chinos with untucked oxfords, jeans with the pant legs rolled up, and canvas sneakers sans socks.

There’s also the wool and leather varsity jacket:

And the varsity windbreaker with striped collar and cuffs, worn with shorts:

And the hooded rain slicker, also paired with shorts:

And finally the untucked, sleeves-rolled oxford accessorized with bicycle:

Further “Take Ivy” influences can be seen in the “Road Trip” video on the Rugger website, which includes bucolic scenes of nature (very Dartmouth), and young men bicycling around a small college town. Or maybe Brooklyn.

Now owned by Gant Pyramid AB of Sweden, Gant is proclaiming a redefining of the brand based on a rededication to its 1949 origins in New Haven, Connecticut. Writes the company on its website:

After years spent scouring the US for vintage originals, sorting through dusty swatches, and searching through our vast fabric archives with an unheard-of attention to detail, the new and improved Gant Rugger is back with a vengeance to reclaim the field with a collection unlike anything else out there.

Unlike anything, that is, except “Take Ivy.”

Further:

We’re one of the very few brands still standing who were right there at the birth of American sportswear during the 1950s, and it’s our heritage that makes us who we are today.

Now don’t think I’m being censorious in pointing out the book and collection parallels: Tradition-with-a-twist is the best approach to making fashion, as it properly balances novelty with respect for the classics. There’s no need to create new forms, as they’ve all been perfected already. So cheers to Gant for keeping the taste for classic American style alive for a new generation.

As for “Take Ivy,” someone just lent me a copy and I can say it’s much more enjoyable in print than in pixels. The style and functionality of the clothes really leap off the page, or rather draw you in, revealing American sportswear at its best.

If you’re interested in The Ivy League Look, I highly encourage you to seek out a hard copy. Try your local lending library. Or eBay. Or a Gant store. — CC

Was John F. Kennedy the most Ivy of US presidents, or did the most important man in the country actually encourage American men not to follow the Ivy League Look?

That depends on whether you’re talking about President Kennedy the nation’s leader, or Jack Kennedy relaxing among friends and family in Hyannis Port.

On assignment for the latest issue of The Rake, I examined the split between Kennedy’s public and private life, and how this was reflected in his wardrobe.

The text of the article is below, or you can download a printable PDF.

Setting the President: John F. Kennedy’s dress sense was central to his public persona, forming no small part of this truly modern president’s enduring iconography
By Christian Chensvold
The Rake, Issue 7

Photographs of John F. Kennedy generally fall into two categories. In the first, we see him at his family’s Cape Cod retreat, sleeves rolled up, wearing khakis grass-stained from touch football, or clad in Nantucket Reds and sunglasses sailing the sea. In the second, his presidential kit, we see another man altogether. Kennedy’s dark suits hang with a certain awkwardness, the shoulders large and high, his two chest buttons both fastened.

Though both are equally iconic, these two images of JFK reveal the sartorial differences between the man’s public and private lives. Privately he was the Choate and Harvard-educated scion of a patrician American dynasty, while publicly he was a progressive young Democrat, commander on the frontlines of the Cold War, and careful crafter of a public image in the new age of television.

This schism makes JFK both the ultimate preppy president — his administration reigned at the height of the Ivy League Look — and an ironic hastener of the look’s decline, undermining the very style he so perfectly embodied. Though Kennedy could hide neither his Catholic faith nor brahmin accent, this first great image crafter of the TV age could strengthen his broad appeal with two sartorial gestures: He would wear two-button suits instead of three-button sack models, and he would eschew buttondown collars. The result, noted LIFE Magazine in 1961, was that the president’s clothes “fail to conform to current Ivy League fashion.”

Before becoming a style setter, Kennedy started out as a ragamuffin. “As a young man he was notorious for his personal disorder,” writes Neil Steinberg in “Hatless Jack: The President, the Fedora, and the History of American Style.” “His boarding-school roommates complained of his messiness, particularly with clothes. He would show up with his shirt untucked, or without socks, or wearing a rag of a necktie.”

Before his marriage to Jacqueline Bouvier in 1953, “Kennedy had been a sloppy dresser who favored baggy suits, clashing shirts and ties, and ratty tennis shoes,” according to historian Thurston Clarke.

With Jackie’s guidance, Kennedy’s style evolved into a paragon of simplicity and understatement. His casual weekend mufti was collegiate and Northeastern — Shetland crewnecks, penny loafers sans socks, white t-shirts, polo shirts and chinos, with a notable absence of pattern. His suits were solids or light stripes, shirts almost always white with a short straight collar, his ties discrete reps and clubs. Like Steve McQueen, another charismatic public figure with subdued taste, Kennedy gave his clothes style, rather than the other way around, a testament to the idea that clothes should never upstage their wearer.

Sartorial simplicity suited Kennedy best because he had star quality, an air of innate dignity, recalled his physician Janet Travell, “that was the product of personal reserve, self-respect, style and a distaste for ostentation.” But there was something else. With his sunglasses and convertibles, ironic wit and military heroics, Kennedy had something no American leader had ever had before: cool.

Much of Kennedy’s cool came from his hair, a Samson’s mane of potent charisma and something Kennedy famously avoided covering with headwear. “In a hat he looked far older and almost unrecognizably ugly,” writes Steinberg. “And he knew it.”

Kennedy’s effect on American taste was palpable. “Kennedy sets the style, taste and temper of Washington,” wrote GQ in 1961. “Cigar sales have soared (Jack smokes them). Hat sales have fallen (Jack does not wear them). Dark suits, well shined shoes, avoid button down shirts (Jack says they are out of style).”

As GQ points out, Kennedy set styles as much for what he negated as for what he advocated, and he stood in favor of two-button suits as much as he stood against buttondown collars. Historians have suggested that Kennedy preferred two-button suits because they better accommodated his back brace. Paul Winston, however, who made suits for Kennedy while working at his family’s legendary clothing company Chipp, recalls Kennedy wearing a brace during fittings at New York’s Carlyle Hotel, but says the button stance would not have mattered.

What is more likely is that Kennedy felt that while he couldn’t hide his privileged background in a television age that required mainstream appeal, he could at least obviate his image sartorially by wearing suits less redolent of the Eastern Elite and more becoming a man in the limelight of international affairs. When asked if suits for the newly elected president would be two-button, tailor Sam Harris said, “Certainly, two button. We don’t follow Ivy League or beatniks. We make gentlemen’s clothes.”

And when it came to shirt collars, Kennedy mocked his brother Robert in the press, telling LIFE, “He’s still wearing button-down shirts; they went out at least three years ago,” and told friend and confidant Paul Fay that his button-down collars were “too Ivy League.”

Privately preppy, publicly the leader of the free world, Kennedy was always an icon. But in the annals of sartorial history, JFK is less an example of a well dressed man than a man with tremendous charisma, and for such men understatement is always the best frame.

“Kennedy was a handsome and important man,” remembers Paul Winston. “That old saying that clothes makes the man? Not really. I think the man makes the clothing.”

Images from Time magazine’s “JFK Style.”

Our recent J. Press scarf giveaway yielded many pearls of wisdom in the comments section, the best of which form a veritable handbook on deportment for the young man just embarking on life’s adventure, which usually begins when he heads off to college.

While studies and girls will be your main concern (they were certainly ours), here are a few things to be mindful of, according to your fellow Ivy-Style readers.

Feel free to leave a comment and add to the wisdom.

* * *

Wake up every morning thinking the day has the potential to be the best day of your life.

Follow your heart and go for it. You’ll only regret what you didn’t do, adventures you didn’t take, lips you didn’t kiss.

Fake it ’til you make it. No one will know the difference.

Try not to be such an asshole. (Continue)

For spring, Sebago has released its classic penny loafer in new colors and with a roughed-out sole and stacked heel. Colors include navy (evidently the hot new shoe color, for reasons Reason can’t explain), sand, white, and light brown (pictured).

The shoes are available now from Sebago’s website and sell for $130. Click here and choose “Alternate Colors.” — CC

Don’t things like this usually come in threes? Click here for The Washington Post’s coverage.

Louis Auchincloss, author of prep-school classic “The Rector of Justin,” plus many novels and stories set among New York’s Old Money, died Tuesday night. The New York Times‘ coverage is here.

And from 2008, The Washington Post’s book critic Jonathan Yardley looks back on “Justin.”

The March, 1991 M Magazine article — of which scans are presented below after the jump (click “Continue”) — is our second article on Brooks Brothers during the Marks & Spencer era.

Along with the previous one from Forbes, the article is part of a cache I collected while doing a paper for a Business 101 course. I titled my paper “The Fleecing of Brooks Brothers?” and chose the company as a subject because as a customer I had a vested interest in the changes going on.

Some of the changes make sense. Wardrobe sizing — the ability to buy separate pants in different waist sizes — allowed Brooks Brothers to fit people with non-standard drops. And wholesaling Brooks Brothers shirts to independent retailers opened the product to customers who were geographically isolated.

So what went wrong? I was uneasy from the start, considering that the best thing the press could say about Marks & Spencer was that they supplied Margaret Thatcher’s underwear. There were brash advertisements, new products, and perception of chasing a younger and hipper customer. There seemed to be a break with the past, and longtime customers lost confidence.

Richard Press, vice president of J. Press at the time, was spot on when he observed, “A number of customers are coming to us who can’t find what they want at places they’ve been shopping in the past. These customers have an allegiance to classical American clothing. Some of our competitors don’t seem to have confidence in that anymore.” — CHRISTOPHER SHARP

Christopher Sharp lives in upstate New York. He is a former community-newspaper reporter who has served in the Navy Reserve for over 20 years, currently supporting the Global War on Terror. He recently acquired the Brooks Brothers cigar label pictured above. (Continue)

As promised, a few notes on the ENK menswear trade show held last week.

For spring and fall, Allen Edmonds will be bringing out a number of updated shoes in the trad category. Three of them are highlighted above, while all six are in the photo below (apologies for the bad shot). (Continue)

Harvard’s financial troubles have been well publicized. The university also made news several months ago when it was announced that it had licensed its name for a contemporary fashion collection called Harvard Yard, and was criticized for selling out its name for a frivolous new revenue stream.

Earlier this week, Wearwolf Group, the company that holds the license, invited me to the ENK menswear trade show to view the collection.

While chatting with the founder and checking out the clothes in the trade show booth, I noticed a piece of marketing collateral sitting on the table. It was a montage of vintage images meant to give potential buyers the vibe of the collection. I recognized a number of images from Ivy-Style, then went back to chatting with the founder, when suddenly I did a double take because right next to Aga Khan is my madras-clad posterior.

It’s true: Harvard is using my ass to sell clothing. I should be getting a cut off the back end. — CHRISTIAN CHENSVOLD

More on the collection and trade show in the next post. Image graciously provided by Harvard Yard at Ivy-Style’s humble request.