Jack’s Back: The Tenacious Return Of Jack Donnelly Khakis

Over a year ago Gregg Donnelly, founder of Jack Donnelly, known in the Ivy Style community for its American-made trousers, was hospitalized for three months after suffering a severe allergic reaction to a prescribed prescription medication. After leaving the hospital, it took Donnelly another twelve months to fully recover. Faced with financial trouble from hospital bills and little income from Jack Donnelly due to his absence, he considered throwing his company out altogether. “I was at a crossroad,” he recalls. “Do I graft back and relaunch? Or do I pack in and start another career?” Driven by his passion for the brand, Donnelly re-launched Jack Donnelly, saying, “I had come too far and built too strong of a foundation to abandon everything.”

Throughout this period and his absence, fans remained loyal and he maintained a steady base of customers. “Most of our customers were very understanding of the situation and continued to support us,” he says. “It meant so much to see that.” Since starting his business and facing immense health challenges through the company’s journey, he has refined his approach to the business and built upon his perspective of running a company. Describing the founding of Jack Donnelly, Donnelly is blunt: “I will say it’s very challenging to start a business by yourself – that is the first lesson.” Adding to this, he says how in the first few years of starting his company he believed there would be a “right time” for everything, before realizing “There’s no time quite like the present.”

Indeed, Donnelly has taken the charge since re-launching by expanding Jack Donnelly and implementing his evolving visions for the company. Throughout, he has remained committed to the same principles he started the company with, namely continuing to make quality American-made products and provide excellent service. And as the company eases in with a new supplier, Donnelly added that production will continue during the ongoing Covid-19 pandemic. With a new business partner, too, Donnelly plans to continue to produce their best-selling Hybrid Fit Dalton Pant in khaki. Moreover, he plans to add additional colors and fits as the company expands, including a new Officer Pant made from 9-oz. Japanese Selvedge Twill, and a 12-oz canvas 5-pocket. In addition, another new batch of products will be available on the website in early May.

Perhaps most significantly for Ivy Style readers, however, is the upcoming release of Jack Donnelly’s Ivy style fit, a trouser he modeled off of the elusive and highly-sought after high rise and tapered-legged pant of the Ivy heyday. Donnelly describes the trouser as having a “long rise” and “straight leg on the slimmer side.” As of now, the company is finalizing samples and, once approved, will begin producing the trousers.

“We’re excited for the future,” he says. “It’s been wild journey, but we’re really only getting started. We want to continue to improve in all that we do and continue to establish ourselves as a go-to American-made khaki provider. Thanks for all of your support. We can’t do without all of our consumers and supporters. To anyone who sent me an email, ordered a pair or two of khakis, visited our website, liked or commented on our socials, posted a photo in our pants, or has been a JD faithful throughout this crazy ride, I see you, I appreciate you, and I need people like you to help fuel this small business.” — JACK M. CARLSON

Gregg Donnelly has graciously extended a discount to Ivy Style readers. Enter the code “Ivystyle” at checkout for 15% off. 

14 Comments on "Jack’s Back: The Tenacious Return Of Jack Donnelly Khakis"

  1. Jacquard Selvedge | May 4, 2020 at 3:13 pm |

    I need to reconfigure my lower torso to fit into these lovely pants.


  2. Mitchell | May 4, 2020 at 3:42 pm |

    Can someone explain what ideal body type for high-rise/tapered leg khakis is?

    Do you have to be a 6’2” male runway model, or is it more of a comfort issue?

  3. “Take Ivy” shows a range of backsides — I mean body types — all wearing this kind of cut.

  4. Jeremy Morehouse | May 5, 2020 at 1:15 am |

    A while ago, I realized how unattractive and uncomfortable Ivy style fit in trousers was, and opted for a a high rise with a fuller cut from the backside down. That was the same time I opted for two-button jackets and cuffless trousers. Now, unlike the Japanese, I can be Trad without wearing a costume.

  5. The Donnelly khakis in the current original fit look pretty good to me. $98 is a very reasonable price for chinos that are hand made in the USA and the 15% discount makes them a bargain. British or Italian made equivalents, e.g. Drakes, are double the price and are often even more. I await the arrival of the higher rise Ivy style fit with great interest, especially if the price is similar. Best of luck to Gregg in these very difficult times. He deserves it after what he’s been through.

  6. Charlottesville | May 5, 2020 at 9:55 am |

    I also wish Mr. Donnelly every success. I have been buying Bill’s Khaki’s M2 fit and having the legs tapered to 8 inches at the cuff, but the new Ivy fit from Donnelly sounds perfect, and the price unbeatable.

  7. For people with short torsos like mine, a high rise pant is not at all flattering. Much prefer a low rise pant to create the illusion of a longer torso.

  8. john carlos | May 5, 2020 at 12:08 pm |

    Charlottesville-I,too, have been a long time fan of Bill’s M2 plain front khakis. I’m going to try the Ivy fit from Donnelly, especially at the very reasonable price.

  9. I will attest to Mr. Donnelly’s outstanding customer service. I have had a couple of unique situations occur when ordering pants from the website, and in both cases, he took care of the concern personally. I am a big fan of his hybrid fit Dalton pant, and I’m looking forward to the Ivy fit!

  10. Old Trad | May 5, 2020 at 3:01 pm |

    Thank God for LL Bean and Lands’ End chinos/khakis.

  11. Matthew Freestone | May 5, 2020 at 3:56 pm |

    @Jeremy Morehouse,

    Re:”Now, unlike the Japanese, I can be Trad without wearing a costume.”

    That’s why I take Bruce Boyer as my inspiration.

  12. Seth Lederer | May 6, 2020 at 2:23 am |

    Bruce Boyer, a gentleman whom I’ve looked up to and tried to model myself on as I’ve tried to find my own way

  13. Gregg Donnelly | May 10, 2020 at 12:46 pm |

    Christian and Jack – thanks for the excellent feature.  I appreciate your time and willingness to help spread the good word.  Ivy-Style has been a supporter of me and the JD journey since the beginning – it means a great deal to me.  I am excited about everything we have cooking – and excited about the future (especially our new Ivy Fit).  Thanks to all the commenters for your kind words and support.  If you need anything from me, or if you just want to reach out, my email is always open gregg@jackdonnelly.com
    Be well and stay safe!
    Gregg Donnelly

  14. I’m going through a cleanup phase of my wardrobe which means pairing down and buying quality instead of quantity. I’m replacing many of my off shore made products with American made and kakkis are at the top of my list. Looks like Jack Donnelly will be a definite consideration.

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