Gregg Donnelly ( And His Two Year Khaki Tour

Editor’s Note:  In reading the comments, kept coming up.  Here’s the origin story, it has a few links to the website in it.  In fact, here’s another.  They are a few days away from a restock of some of their categories.  I will stay in touch with them and let you know, but check out the site today too to see if they have the right pair for you.  Donnelly is a good guy who is single minded about being excellent about every aspect of his khakis.   It’s worth a look.

Gregg Donnelly spent two years studying his craft, and the rest of his life perfecting it.  His craft?  Khakis.

You know how you start a company, right?  Starts with an idea, something you can make or do.  Then you ask yourself, how am I gonna make or do this better/different.  Then you write out a five year plan.

Which is a total waste of time.  If you started your business out in, say, 2019, you’d be in year three, right?  Anything unexpected happen in the years since that may have impacted your five year plan? Here is when it is a bad idea to have a plan.  I have two favorite economic concepts.  One is the Point Of Diminishing Return.  The other is Opportunity Cost.  Point (or Law, depending on what you study) Of Diminishing Returns is easy to understand.  There is a point at which you have maxed out your investment and it stops making sense to continue.  For example, you have three barber chairs that you rent out to barbers.  You figure, if I add three more barber chairs, I will make twice the money, right?  Except you don’t, because now you are spending half a week managing the chairs, your insurance goes up with your tax bracket, you have to invest in a whole new appointment and cashier system because now you have twice the scheduling, oh, and you need more space and it was easy to find a railroad space that can house three chairs and a sink, but now you need storefront, serious footage, and that goes for way more a square foot.  So it turns out you are doing more work, for the same money.  And if you applied that energy elsewhere, say to marketing the three chairs, you would see a higher return.   Opportunity Cost is a horse of a different color.  It is essentially the weight of the cost of one opportunity against another endeavor.  So if you write a five year business plan, for example, there is a cost.  Your time, whomever you pay to look at it, etc.  The return is, you have a plan, the odds against you staying with that plan are pretty high.

Gregg Donnelly is smarter than me.   Gregg is the founder of, and if you are one of those who doesn’t read the comments here, his khakis come up an awful lot.  So much so, in fact, that I reached out to him to find out about the khakis. And I met a guy who LIVES for khakis.


Gregg Donnelly at home. Well, in his natural environment anyway.


Here’s how he started his business. “I studied finance in college, that got me in the game,” Donnelly said. “When you are younger, your risk tolerance level is higher, and I love khakis.”

Love might be an understatement. Donnelly loved khakis so much he started out with an admiration of quality in khakis that continues today. “There were always companies that produced khakis well,” he continued, “but I had this thought. There were companies that had great construction, but the fit was off. There were companies that used quality materials but the style was off. I thought, what if I tried to be excellent at every aspect? At everything that has to do with khakis? Design. Construction. Quality. Materials. You name it. I thought if I did that, my khakis would be different.”

And ok, so far so good. But this is where I wanted to go back to Gregg’s professors and get a better sense of his finance education. Because his next decision in starting was to take two years, TWO YEARS, go on the road in his car with the cassette player, and learn as much as he possibly could while he sourced the greatest vendors the the country had to offer. That Point Of Diminishing Returns we were just talking about? I would have thought it would be about four hours into his trip when he flipped Tina Turner’s Private Dancer cassette over for the third time. I was wrong.

Donnelly was right, and for the next two years, he drove all over the country, interviewing, touring, researching, thinking, and sourcing. “That is still my favorite part,” Donnelly says now. “To think about and evolve each product. To make relationships with vendors and form an American team of excellence and tradition. I would drive from state to state, I wanted to make sure I met everybody. Finally in Georgia I found a company that did construction the best, and started with them.”

Finally, Donnelly got home, and astonishingly, he had a few bucks left. Not enough to start a business, but enough to throw in with his parents, and do a first run of 500. “We started lean, for sure. Back then, making a website was a big investment, so it wasn’t just the pants. Today, selling online is turnkey, but when we started out you had to do everything from scratch.”

It certainly worked. Today? (that’s a link, btw) offers 3 different styles and 4 different fits, all made in America, all to Donnelly’s meticulous standard.   The M3 Tapered is advertised as “inspired by the classic Ivy Style that hit big in the 1950s and 60s with a traditional, longer rise combined with a slim straight leg.”


The M3 Tapered Twill Chino from the website. Visit for more.


“I love feedback,” Donnelly concluded, “My cell phone is listed on the site, you can text me directly.  That’s part of our work, American made, the best materials, old school methodology, no middle man so we can keep the cost down, and accessibility.”

A personal observation.  I spent time with Donnelly on the phone, and the guy loves to talk khakis.  I have met people who are bored by what they do, jaded after years.  Donnelly is the exact opposite.  He is authentically obsessed with khakis and getting them just right.  It was refreshing.




20 Comments on "Gregg Donnelly ( And His Two Year Khaki Tour"

  1. Hardbopper | April 26, 2022 at 9:24 am |

    Is it not acceptable to steam press a crease into chinos?

  2. Great post!
    I have two pairs of Jack Donnelly’s M3 “Ivy” fit, as well as a pair of the M2 straight fit, and can confirm these are some outstanding pants. My favorites to wear, actually. Perfect all-season weight, too.
    *They’re not vanity sized, FYI. If it helps other readers on sizing, my 501s and my chinos from elsewhere are 33W, but my Jack Donnellys, like my dress trousers, are 35W.

  3. Hardbopper | April 26, 2022 at 9:56 am |

    How would you describe the difference between the M2 and M3? The rise?

  4. Nice post. As a long-time (but not intentionally loyal) Bills Khakis wearer, this is a story that makes me want to get a pair. Thank you.

  5. Basic Trad | April 26, 2022 at 1:33 pm |

    I have never come across any firm that provides this many details about measurements and differences between fits. That alone means that Greg deserves an order from me.

  6. Basic Trad | April 26, 2022 at 1:34 pm |

    I forgot to include the link:

  7. Frederick J Johnson | April 26, 2022 at 2:40 pm |

    I am a huge JD fan and customer, having given up Bills. JD’s just fit better although the construction, fabric, etc. are very similar, or so to me anyway. I get the M1 fit because I like the baggy fit which is not everyone cup of tea.

  8. Hardbopper | April 26, 2022 at 3:22 pm |

    M3 Tapered has a higher rise than M2 Straight. Which is the more heavily weighted criteria and why? and is this universal?
    I like what I see, that is, I like the pockets and what appears to be good stitching. I would prefer the added security of a double button tab closure (one hidden)…and lap seams…but I’m dreamin’ on that one. An extra belt included would be easy.
    Mail order is a tough business for customers, too.

  9. Hardbopper | April 26, 2022 at 3:25 pm |

    An extra belt loop…

  10. Charlottesville | April 26, 2022 at 4:40 pm |

    As a satisfied Bill’s M2 wearer, I must say that these Donnelly M3s look very good. I need to give them a try, although I currently have several pairs of Bill’s in rotation, including a new pair that just arrived last week, so may not need another right away.

  11. AtlantaPete | April 26, 2022 at 4:59 pm |

    I have a few of the M1 relaxed fit and told Gregg in an email exchange that they are very close to the Brooks Bros. long rise flat front khakis I bought in the late ’60s and early ’70s (well before the demise of BB). I think they are the best available.

  12. Also, curious about the “hybrid” “Dalton”. Still in production? Specs?

  13. Philly Trad | April 27, 2022 at 2:17 am |

    Re: Steam-pressing a crease into khakis:

  14. @Hardbopper, the rise isn’t that different between the M2 and the M3, maybe just a tiny bit lower in the M2. There is some more detailed measurement info on the Jack Donnelly site than I can provide at the moment. The other thing I can say is the main difference I notice between my M2 and M3 pants is the taper: The M3 is meant to taper more, and it sure does, but not at all in a way that is calf-binding. Really great fits, the both of them.

  15. The M1’s descriptions say “sits on the waist”. The M3’s description says “long, traditional rise combined with a slimmer thigh & a nicely tapered leg….sits high on the waist”. Yet the M1’s back rise is higher than the M3’s but the front rise is lower. I want the highest rise so which one, in practice, would suit me best? It might be better to get the M1 and ask my tailor to taper the leg.

  16. Bully for Donnelly. Great piece.

    This is the khakis/chinos equivalent of Mercer & Sons — sales are direct to customer/client, American manufacturing, honesty/transparency about the product(s), and a welcoming oppenness to customer/client feedback. The owner is invested in all aspects of operations and quality control.


    I’d like to see a few wool fabric options but I acknowledge the wisdom of keeping the vision simple and mission/goals narrow in scope. Look at what (too much) expansion did to the original Bills Khakis.


  17. Craig Sevde | April 27, 2022 at 12:45 pm |

    Someone more anal than myself! Refreshing.

  18. Anyone else show the J.Press warehouse sale like it was Supermarket Sweep?–We’ll see how much of an order made it through!

  19. NaturalShoulder | April 27, 2022 at 11:12 pm |

    A very flattering write up of Jack and his offerings. I agree with S.E. About benefits of doing one thing extraordinarily well and focusing attention and resources of that task. I think I will place an order for the M3model.

  20. G. Ellery Cobbold | April 29, 2022 at 9:36 pm |


    My 35″-inch waist Buzz Rickson 1942 chinos have a Chrysler Building-high 14″ front rise, but they sit lower on my waist than my 35″-inch waist Bills M1s because there isn’t as much room in the top block. I assume that the back rise is the culprit.

    In 2010 Boyer the Great and Robert E. Bryan conducted what John Tinseth called a ‘blind chino tasting’ and named Bills’ late, lamented Bullard Field Pant the most traditional:

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