Khakis are a versatile staple of one’s menswear wardrobe. They can be dressed up with a sports coat and oxford cloth button-down shirt, dressed down with a polo or t-shirt, crease or no crease, plain or cuffed hem, the possibilities are endless.

Within reason. Please don’t wear them with a dinner jacket.

Almost nine years ago, I first got in contact with Gregg Donnelly, founder of Jack Donnelly Khakis, after hearing about his company on menswear forums and wanting to know a little more. We talked for a bit and he generously offered to send me a pair of the Dalton Pant, which was deemed a “classic fit”, for review on my blog. These were definitely more like World War II khakis in fit, having a generous 19” leg opening and a lot of fullness through the leg. Nonetheless, I found them to be good quality and quite fairly priced for being American made. There were more colours and products when they first debuted, including shorts and pleated trousers. Other fits would come later in their lineup, so you needed the help of an alterations tailor if desiring something slimmer.

Jack Donnelly Khakis launched a decade ago, in 2011, and relaunched in 2018 after two years of Gregg being on medical hiatus. The product selection was slimmed down, both in the number of products and the dimensions of them. The M1 Relaxed, which is what the classic fit model is now known as, now has a trimmer leg opening at 17.25” (for size 35). They’ve also renamed the Dalton Pant to the Twill Chino, which is a little more intuitive to prospective customers for what they’re getting. Of course, some may object to this since chino cloth is, and chinos are, technically different from the Cramerton twill used in khakis like these. You can have any colour you want, as long as it’s that iconic beige “khaki” shade. This isn’t necessarily a bad thing. By focusing on a few good products and doing them well, it’s possible for a small business to keep their expenses low. The quality is definitely better than it used to be. While I liked the review khakis I received in 2012, and further ones I got on my own from them afterwards, there were some minor issues in the strength of the buttonholes as well as the pocket bags fraying quite a bit on the edges. The seams weren’t all that clean in some places. The waistband could also feel a little floppy. I don’t believe this is the case with the recent batches. The buttonholes seem very strong and the inner construction is definitely much cleaner at a glance. The waistband feels a lot more solid. I feel like they’ll hold up much better after many washes. Additionally, they now have the fit designation sewn on the inside pocket bag so, if you have different fits of khaki for different purposes (as I used to), a quick glance inside will show you what you need to know. The label is now inside the waistband and pretty no-nonsense, with the Jack Donnelly logo and the size. Minor criticism is that the fit designation could also go inside the waistband. First impressions were very good.

There is a small change that may be controversial with khaki purists. The back pockets no longer have the traditional arrangement of being single-jetted with the left one buttoned. Rather, both of them are now double-jetted and buttoned as with most suit trousers these days. It’s interesting to note that American World War II khakis actually had two double-jetted back pockets without buttons, a double-jetted watch pocket in front that was offset from the waistband, and slanted side pockets with a slight inward curve. Most modern khakis that claim to be inspired by that also don’t have any of the flat felled seams the originals did. The single-jetted back pockets many associate with khakis appear to have come with the 1950s (Korean War era) production of them, along with the watch pocket changing to single-jetted. The left back buttoned pocket and the on-seam side pockets wouldn’t come until the Vietnam War along with a zip instead of button fly… and a hook closure waistband. Is this all confusing? A little. So really, one’s choice of details when making khakis can come from three or more different “vintage” decades of U.S. Army uniform production, even though we often associate them with the Second World War.

Fortunately, the Jack Donnelly Twill Chino still has the vestigial, mostly-for-style-now watch pocket (which many call a coin pocket these days) in front which is located along the lower waistband seam. It’s a feature I prefer on all my trousers, even suit trousers, since I can keep my key fob in it. I may be in the minority there, but if not… watch pocket fans, sound off in the comments below. Don’t worry, they haven’t committed the deadly sin of having slanted side pockets. They are still the vertical, on-seam pockets Trad and Ivy League style followers know and love. I personally feel that keeping details simple helps khakis be as versatile as they are. One or both of the buttons on the back pockets could stand to go. But it’s not a big deal. If Jack Donnelly ever chose to make accurate reproductions of vintage khakis, I wouldn’t complain either. Especially if they were offered in more modern fits. But Gregg is successfully selling the styles he personally prefers. I think that’s admirable.

The M3 Tapered, which I received, echoes the fit of khakis seen in the 1960s, particularly those worn by younger men on Ivy League campuses. They have a higher rise and tapered leg — 12.25” long and opens to 16.25”, respectively, on my size 35 pair. I suspect a lot of those students had war surplus khakis narrowed by a tailor to look more hip and cool. I could be wrong. They are not quite the ‘40s-by-way-of-’60s Steve McQueen khakis seen in The Great Escape. Those still had a bit more fullness through the seat and leg while being nowhere near as baggy as the genuine issue. You probably want the M1 or M2 model for that look, though the rise will be a little shorter. For their slimness, the side pockets of the M3 don’t flare a whole lot, which is saying something since I have quite a rear end. They do ride up a little in back like some of the pairs from their original run. This is where one of my pairs from Polo Ralph Lauren is actually superior in fit, though worth noting it also has a gusset in the crotch. Again, I have a little more “junk in the trunk” than most and it’s a problem I run into with many less-than-traditional fits off the rack. Most people aren’t going to have that issue. Also, wouldn’t you rather pay $125 for American-made khakis instead of almost $100 more for ones made in Indonesia? I think the choice is easy here. I was sent the size 35 since I have a 36” waist (there is about an inch of vanity sizing added, which is less than many brands have) and they fit pretty snugly in the waistband. I think anyone with my issues in the seat could size up and have the waistband taken in if needed. In any case, take a look at the size chart and make sure you measure yourself accurately. Don’t just assume you know it because your jeans and trousers from one brand fit and are labeled a certain number. Manufacturers are building in a lot of vanity sizing these days. I wear a 33 in Gap jeans… those filthy liars.

Being cotton twill, they’re obviously not going to look as polished as a pair of worsted wool suit trousers. But the fit still has enough ease that I could probably wear them with a crease if desired, even though it may not hold long. I’m going to continue wearing them without a crease since the fit lends itself to a more casual look. Those who want to wear them with a crease, perhaps even a sports coat and tie, might have a better time with the M1 or M2, which are a little more forgiving in fit and thus may hold onto creases longer. I personally find it easier to press my khakis straight, rotating the leg as I go, than trying to maintain a crease in front and back of the legs. Particularly when these get machine washed instead of dry cleaned. You can, of course, wear your khakis rumpled with an equally-unkempt OCBD shirt if you really want to. I would at least attempt to dry them on the air puff cycle, then steam them.

They offer a complimentary hemming service by email, which is a great added value. They can accommodate pretty much any request: Topstitch, blind stitch, or cuffs. The plain hems can be done to a half inch, like the product photos, or full inch from the bottom. They default to the topstitch an inch from the bottom for hemming requests and build in a quarter inch extra for shrinkage. This service is available for final sale only. Many American Trad enthusiasts prefer a cuff on their khakis. I personally have found it more difficult to press a cuff at the bottom than with a plain hem. More difficult than with a pair of wool suit trousers at any rate. But the advantage of getting a cuff is that it can be turned in and made into a plain cuff when the bottom edge wears out. Choose accordingly to your whims.

Mine were hemmed with a topstitch a half inch from the bottom by the good people at Tailor Cooperative. It gives them a casual appearance, a little more jeans-like, which I think is appropriate for the narrow leg opening. Once I had them hemmed, I wore them for three days straight with three different shirts, I liked them so much. What can I say? They’re quite a versatile pair of trousers. Some may criticize me for going with a slight break instead of no break at all as is customary in online menswear circles. However, I find cotton trousers tend to ride up a bit with wear for whatever reason, especially sitting down and standing up multiple times in a day. There’s also the possibility of them shrinking a bit more in the wash as time goes on. No judgement from me if you prefer the no break or even Take Ivy highwater look. There was one small issue where some of the reinforced stitching at the top of the left pocket came out after washing. I was able to clip it and haven’t had any problems since. From what I can see, their free return and exchange policy would not cover this since garments must be unwashed, unworn, and unaltered. If I’m being picky, I also think the waist button could be moved over a quarter inch to better align the fly.

I really like the current incarnation of Jack Donnelly Khakis and would recommend them, though I hope the reinforced stitching holds up better in the future. There are four different fits and they are a good value for the price. Gregg has advised me that all the previous colours, before last spring’s onboarding of a new production partner, will return very soon. I would like to see them branch out a bit more in styles, perhaps into forward pleated or button fly khakis. But overall I think khaki enthusiasts, or those simply putting together a classic wardrobe, will find something to like here.

Disclaimer: This review was made possible by Gregg Donnelly, of Jack Donnelly Khakis, sending a product to the author for evaluation purposes. Every effort has been made to remain objective and consider quality versus price.

Giselle is a menswear expert and freelance writer who gained an interest in dressing well upon re-watching James Bond movies, researching what makes him so stylish, and later engaging with others in online spaces to learn more. She has written about tailored clothing for over a decade through her blog, Nouveau Vintage, after being inspired by others to share her passion.