Since their invention by British soldiers in India, who tried to conceal dust by dying their trousers with tea, khaki pants have been a menswear staple marked by overabundance. Department store racks are lousy with them, and new brands appear and die out yearly. The khaki market is a hard one to win a share of, and an even harder one in which to stand out.

Gregg Donnelly thinks he can do both. “There isn’t a go-to player in the khaki market,” says Donnelly, who founded Jack Donnelly Khakis in 2008. “It’s near impossible to consistently find a quality pair. There are so many companies making khakis right now, but I have yet to find a pair that is truly worth my money.”

It’s true that most khakis aren’t made very well. They sag in the seat, the fit and finish are poor, and they fray and fade poorly. Most are made overseas. The few American-made, high-quality brands are prohibitively expensive. It’s ironic for a product synonymous with traditional American style.

Donnelly thinks the solution is attention to detail, and he’s arranged his business accordingly. “Because our headquarters are less than a few hours from where our khakis are actually made,” he says, “we are afforded the ability to keep a close eye on the entire khaki-making process, and to make sure they’re manufactured to our exact specifications.”

Those specifications include a roomy seat and thigh and a waistband designed not to creep up the hips during wear. Jack Donnelly Khakis’ introductory Dalton pants are available for sale exclusively online, in khaki and stone, with pleats or without. Dalton shorts are available in the same color and pleat options. The cost — $88 for pants, $68 for shorts — is steeper than most department-store khakis, but shipping to anywhere in the US is free. Returns, for any reason, are free as well.

Each pair comes unfinished. Having them hemmed is one step more than would be required of store-bought pants, but, given their quality and Gregg Donnelly’s enthusiasm, a day at the tailor’s might prove a small investment in a pair of khakis that’s actually worth your money. — ANDREW S. EASTMAN

Andrew S. Eastman is a 2007 graduate of Dartmouth College, where he was a member of the rugby team and wrote for The Dartmouth Review. After a short stint at a Boston public relations agency, he began pursuing a law degree at the Saint Louis University School of Law.

Until somebody finds the official “Take Ivy” video (our man in Tokyo is working on it), this may be the closest thing to surface so far.

For the past couple of months I’ve been subscribed to the Princeton Campus Life YouTube channel. Most of the archival footage has been recent or early twentieth century. Then the other day I noticed something closer to the heyday: the crew video from 1948-50. So I skimmed through the channel’s videos again and found an absolute gem: a 25-minute, professionally shot (and scripted) orientation film from 1962.

It’s all here: “Princeton” haircuts, stretched-out shetland sweaters, white socks and no-break trousers, natural-shouldered jackets, collar rolls and ties askew, bow-tied professors, pipe-smoking in the classroom, touch football on the lawn, bicycling across campus, and khakis as far as the eye can see, all from the school most credited with setting the styles of the Ivy League Look. — CC

It’s Menswear Market Week here in New York, and I’ve spent the past few days at a couple of the trade shows. First up, Designer Forum, sponsored by the Custom Tailors & Designers Association, the oldest trade organization in the US.

Pictured above are rep bow ties from Collared Greens, which has combined the preppy, domestic manufacturing, and eco trends all into one. Based in Sun Valley, Idaho, the brand showed neckties and brightly colored, organic-cotton polo shirts. (Continue)

Think you’re smart? Think you’re — you know — Ivy League smart?

Then see if you can figure out the cryptic meaning of this vintage Chipp emblematic necktie.

Pictured are four motifs. They are:

A clock reading 3:55

An empty whisky bottle

A woman with one breast exposed

A toilet

What does it mean? Hint: It’s about baseball.

Click “Continue” for the answer. (Continue)

The latest issue of Singapore-based The Rake just came out, with the following piece on the past and present of madras, for which I interviewed Paul Winston, Ethan Huber of O’Connell’s, and Brooks Brothers merchandiser Jeff Blee.

American Indian: Madras, named for the Indian city where it originated, remains a distinctly yankee summer staple
By Christian Chensvold
The Rake, issue 10

Though Brooks Brothers and Chipp were just across the street from each other — at 44th Street and Madison Avenue in New York City — their customer base was miles apart. That’s why one summer evening in the early ‘60s, Chipp employees moved dozens of unsold patch-madras sportcoats from one side of street to the other, changed the labels from Brooks to Chipp, and started ringing up sales the next day.

It’s one of Paul Winston’s favorite stories. Fresh from college, he had just joined his father’s legendary company Chipp, purveyors of the Ivy League Look but with a predilection for experimentation and whimsy — like Kama-Sutra linings in sober grey-flannel suits. This creativity also gave birth to the patching of madras, that comfortable, inexpensive and quintessential summer fabric. The fateful “Late-Night Madras on Madison Merchandise Swap” consisted of sportcoats from a third party used by both Chipp and Brooks Brothers. “We couldn’t get patch-madras sportcoats in fast enough, and Brooks couldn’t sell them,” Winston remembers. “Relatively speaking, we were considered edgy, and they had old-line, conservative blue-blood customers who looked down on it.”

The passing of time makes fertile ground for irony. Brooks Brothers has all but declared 2010 the year of madras, offering dozens of products in categories from shirts and shorts to sportcoats, ties, pocket squares and even loungewear. And guess what? Patched items are the best sellers.

“It is an interesting year in terms of madras,” says Jeff Blee, divisional merchandise manager of men’s furnishings for Brooks Brothers. “We made a much more sizable investment in it this year. It fits the two ends of the fashion spectrum: It can be very subdued and traditional in a Nantucket way with blues and reds, but can also be a good vehicle for what I like to call Palm Beach Prep, which is a little more over-the-top in terms of color, with pinks, greens and oranges. (Continue)

Phil Sears Schoonmaker wears a black knit tie 98 percent of the time. This one preference serves as a symbol for his entire approach to dressing.

Thirty-seven-year-old Schoonmaker, a New York-based business process consultant, is a living embodiment of the idea that less is more, of restrained taste and bold simplicity. With his superb balancing of the hip and traditional, he’s a testament to the timeless appeal of the Ivy League Look.

In addition to knit ties, Schoonmaker digs suits with narrow lapels, old and puckered oxford shirts, engine-turned belt buckles, canvas sneakers, selvedge denim, and vintage Timex watches. (J. Crew, who’ve been using real people in their catalogs lately, should grab this guy as their next top model.)

Ivy-Style recently spoke with Schoonmaker about his perfectly simple and simply perfect style.

IS: Describe your business attire. What kinds of suits, shirts, ties and shoes do you wear?

PSS: My style is guided by simplicity. I wear suits and sportcoats cut in the traditional Ivy League manner and prefer fabrics that are more casual in nature. I seek out vintage Chipp and Brooks Brothers exclusively, and purchase my custom-made items from Paul Winston. His passion, creativity and attention to detail are a rare find.

My shirts are cut slim with a button-down or tab collar and a flap pocket. I purchase all my shirts from Mr. Tom Davis and the made-to-measure program at the Madison Avenue Brooks Brothers. Mr. Davis has been with Brooks Brothers for more than 40 years. He is a consummate gentleman and one of the best dressed men I have ever met.

I wear a black silk knit tie 98 percent of the time. When I’m not wearing a black silk knit, I wear one of my vintage unlined Brooks Brothers rep ties. My preferred shoe is Alden’s longwing model in either color eight shell cordovan or brown suede. I also wear Alden’s unlined suede chukkas, especially for travel. (Continue)

Last summer, when I posted a photo of myself on the front page of Ivy-Style, I was also wearing madras. Of course, that was a shot from the rear. This year I’m showing my less flattering side.

Recently, while researching a story on madras for The Rake, I spoke with Ethan Huber at O’Connell’s and he told me about the deadstock bleeding madras sport coats he has stashed away, with some dating back to the ’60s. I told him I was looking for something blue, and he dug up this one for me.

It’s paired with a blue oxford shirt, navy knit tie, Irish linen square, and —outside the frame — silver tie bar, charcoal tropical worsteds, navy surcingle belt and beefroll penny loafers.

Just the outfit for warm summer nights dancing under the stars. — CC

Eager to reinvigorate a stodgy brand in the wake of the Americana fashion trend, Bass is preparing a new marketing campaign aimed at “hipsters,” Harbor Footwear spokesman Jason Lazar told Ivy-Style.

Curious, we probed Lazar, the excutive vice president for Harbor, which holds the footwear license for G.H. Bass & Company (which is owned by Phillips-Van Heusen). Here’s what he had to say:

IS: Tell us about the resurgent interest in Bass shoes.

JL: Bass Weejuns first hit the market in 1936. They are a collection of timeless styles that aren’t subject to fashion whims. At various times their popularity has fluctuated in a relatively narrow range, but they have always been a part of the mainstream. With the resurgence of all things Americana, coupled with that vintage vibe that’s been increasingly prevalent, Weejuns are again enjoying widespread acclaim and approval in the marketplace.

IS: How are you reinventing the brand to attract new customers?

JL: Past marketing efforts have portrayed the brand in a very New England manner: i.e. lots of picket fences, clapboard barns and very pretty people. Starting with Fall 2010, we’re showing the evolution of the brand that reflects its downtown, coolly sophisticated appeal. Gone are the fences and barns, though the pretty people still remain. Photo locations include Brooklyn and the Lower East Side, a far cry from the Nantucket scenes of the past.

Models this season have also edged noticeably younger to better reflect our targeted demographic. It’s a strategic move to better capture its attention through more realistic, real-world cues and attributes. In addition, we’ve committed to a billboard overlooking the High Line Park during the month of October, just to be able to reinforce the Bass message in a new medium in a location that is outside the usual expectation. Bass for fall will definitely have people talking. It’s not what people have been used to, and that’s a good thing.

IS: What are some of the shoe styles you’ll be targeting at the younger demographic?

JL: Women’s and men’s bucks and saddle bucks on brick-color soles, and classic Weejun pennies along with the drop-tassel Weejun in black and burgundy box leather.

IS: What about quality? Longtime Weejun wearers are quick to note a steady decline over the past couple of decades.

JL: The Weejun of today is by far the best quality shoe in the marketplace priced under $100. It is a true-moc construction and handsewn on the last. Many consumers may think that the quality has declined over the years due to the fact that the Weejuns are no longer made in the USA, but all materials and workmanship are consistent with the Weejun made years ago.

Pictured above is a shoe from the Mark McNairy for Bass collection.

For a certain breed of trad purist, there are only four shirts worth wearing: oxford-cloth button-downs in white, blue, pink and yellow.

White and blue are everyday staples of the office wardrobe, and pink is the iconic color, leaving yellow in fourth place, underappreciated, trickier to match, and less flattering. It’s too colorful to be a business basic like blue and white, yet lacks the legendary status of pink.

I decided to check with Brooks Brothers merchandiser Jeff Blee to see just how the yellow oxford stacks up against its rivals.

First off, Jeff had to qualify things: Not every Brooks store is merchandised the same. Some stores only sell white and blue shirts, so yellow isn’t even a choice (ecru, the only other solid oxford available at Brooks, is so obscure as to hardly warrant mentioning).

So rather than look at sales companywide, we opted to just look at sales at the Madison Avenue flagship, where the four main solids are stacked right next to each other. Here’s how the sales break down:

White: 48%

Blue: 38%

Pink: 9%

Yellow: 5%

What do these numbers mean? For one thing, there are almost 10 times as many white shirts sold as yellow. Moreover, there are also nearly twice as many pinks sold as yellow. However, in the South, Blee noted, the margin between pink and yellow is much smaller.

Those who are violently allergic to non-iron shirtings will be pleased to learn that sales of must-iron oxford button-downs are growing, according to Blee. The shirts are attracting new customers thanks to Brooks’ new slim and extra-slim fit options. Kudos to Brooks for keeping a classic alive for everyone by offering updated variations. (Continue)

Now that summer is officially here, it’s time to celebrate seersucker, one of summer’s quintessential fabrics.

Haspel, founded in New Orleans in 1909 and credited with popularizing the fabric in the US, has done just that by holding a contest called “Sport Your Seersucker,” with the grand prize a trip for two to The Big Easy.

Haspel is looking for unique ways of sporting seersucker, and invites participants to submit their photos to Haspel.com. The contest runs until August 15.

Judges include a couple colleagues of mine: Durand Guion, whom I interviewed for the LA Times, and Karen Alberg-Grossman, editor-in-chief of the menswear trade magazine MR.

Just what does Haspel mean by “unique”? Here’s what they said in a press release:

“As part of seersucker’s resurgence this season, we are seeing it worn in more modern ways: paired with jeans, shorts, T-shirts, tuxedo shirts and even motorcycle jackets,” said Jeffrey Ammeen, Haspel’s creative director. “Haspel is challenging people across the nation to tap into their inner trendsetters and submit their most creative, individual seersucker looks.”

Of course, you might just win with a classic look as well. As for the prize:

The grand prize includes coach airfare for two from anywhere in the United States, transportation to and from the airport, a three-night hotel stay, dinner for two each night in some of New Orleans’ finest restaurants, breakfast each day, and a tour of the French Quarter.

Think of it as a “What Are You Wearing Today?” forum thread with a payoff. — CC