Jack Donnelly

Earlier this year, we received a query from one of our readers, asking if we’d had an opportunity to sample the Jack Donnelly khakis. We had not at that point, but we made a mental note to add them to our wish list.

When I went searching for a pair of slim cut khakis, I first gave Bills Khakis a try. We’re mighty fond of Bills in these precincts, so I tried on a pair of their M3 trousers (the slimmest of their three cuts). The results were not inspiring. The low rise did not flatter my middle aged body, and I resolved to stick with the middle of their three fits, the M2, whose dimensions are much more sympathetic to my shape.

So I turned to Jack Donnelly. Like Bills Khakis, Jack Donnelly offers three distinct fits. And like Bills, Jack Donnelly manufactures its trousers in the United States.

But before I pulled the trigger, I dropped Jack Donnelly an e-mail, inquiring about the rise measurement on the slim cut trousers. The response was heartening. The trousers, even in their slimmest iterations, feature a generous 12″ inch rise.

A Brief History

The khaki trouser is not an American invention. That distinction belongs, as it does with much of our classic clothing, to the British. By the time of the Second Boer War, khaki had become firmly ensconced in British military culture. Other armies followed suit, and by World War II, the khaki trouser was an indispensable part of an American solider’s uniform.

British soldiers in their khaki uniforms

But its true cultural ascendancy owes much to the G.I. Bill. In the war’s aftermath, millions of veterans filled college classrooms across the country, and their military khakis were pressed into civilian service.

Over time, the khaki trouser became one of the pillars of the Ivy League look. And while the jeans-centric hippie culture of the late 1960s and early 1970s¬† dimmed the khaki’s cultural luster, by the early 1980s, on the strength of the Official Preppy Handbook, khakis had come roaring back.

Jack Donnelly

Made in the American south, Jack Donnelly’s khakis are some of the finest khakis we’ve ever had the privilege of wearing. They come in three fits (original, hybrid and slim), six colors and two weights. They’re similar to Bill’s in many ways (strength of construction, durability of fabric), and, in truth, it would be hard to choose between the two, but in the slim fit category, Jack Donnelly¬† has the edge because of its aforementioned higher rise.




Unlike Bills, they are sold online exclusively. They run $105. For those reared on cheap, foreign-made Dockers, the price might seem a bit deer. But I can assure you that these are worth every penny.

Here are the details: curtained waistband, metal zipper, 8.5 ounce cotton twill, unfinished bottoms allowing you to have cuffs added (at least 1.75 inches please).


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