Easy and Elegant Life

The Search for Everyday Elegance and the Art of Living Well.

Dusting Off the Khakis


Some thoughts on khakis. Everyone has a pair and quite a few have definite opinions about fit, cut, style, etc. (For a great primer head to The Selvedge Yard.)

I’ve worn khakis for a long time now. Wasn’t born in them like some I know. But they were standard prep school fare and I got to prep school in 1980. For my money there are two kinds of khakis, dress and casual. I know that sounds odd coming from me, but I had a wonderful pair of seriously heavy duty full cut double pleated and cuffed khakis that were my dress khakis. I have to have them starched these days to make them stand as straight.

“Pleated?” you may snort.

Yes, pleated. And when my waist was a cool 29″, it didn’t make a bit of difference. Wish I had a pair just like them now (at a more appropriate waist size.)

And that brings me to my point. I hear a lot about flat front khakis. Mostly that they are more flattering. OK, I’m game. But there is more to it than removing pleats. Fit, as we know, is everything. But let’s also take a moment to think about cut. And a little history.

Pleats were pretty standard fare on men’s dress trousers up until cloth rationing made them, and cuffs (turn-ups), undesirable for clothing manufacturers. Pleats are more comfortable to wear, especially when seated. They also disguise imperfections nicely — when worn correctly at the natural waist and are suspended from the shoulders with a pair of suspenders (braces.) Belts and pleats, that’s where you can run into trouble if the trouser slips beneath your waist to rest on your hips, the pleats pop open. Avoid that and you’re doing all right.

Can khakis be elegant? The former military trouser constructed of heavy twill, with the high rise waist and full cut leg is tough to pull off. There is plenty of room in the seat, plenty of room at the knee and a universal length of 36″. Provided that you are trim enough, they flatter. The advantage to the higher waist is that it sits nicely under your blue blazer without letting acres of billowing shirt and belt show.


Now those are three fine examples of the male of the species. I’m willing to bet that there was a tailor involved in the filming of “From Here to Eternity.” Here’s what happens when the Trousers, Cotton, U.T. are simply hemmed and heavily starched.

(What a Sad Sack. I opened a foot locker and discovered a few pairs of government issue khakis that were my father’s. These date from 1967. I’m working on breaking the starch on the earlier, button fly models.)

Cotton (and linen) “show work.” That is they do not allow for re-alteration (specifically letting out or easing seams.) Which means you have one chance at getting it right at the tailors. Too tight and it’s back to boot camp to work off a few pounds. The men who wore those khakis were in pretty good shape for the most part. Even the officers.

That’s Cap. Philip J. Corso being given a commendation in Rome in 1945. This is years before he helps hide alien technology at Roswell.

So, you see, fit plays into this again. There are models that replicate the military specifications for khakis, most notably Bill’s Khakis, but I’m found the rise to be a bit shorter. The best were the no-longer-produced-ahead-of-their-time Dockers (Yes Dockers!) K-1 Cramerton cloth version.


But khakis were also worn pleated.


The Bill’s Khaki’s version. I believe are based on British Officer’s khaki trousers. They feature double forward pleats.


The trick to wearing pleats and a belt is to buy khakis in heavier weights. (Starch helps, too. You’ll notice that these are a mess. I rarely wear khakis out of the house.)

But what I suspect is the flattering cut to which most refer, is the “new” low rise, slim cut flat front. They have the advantage of resting on the hips (thanks to the low rise) and, so, will remind you of blue jeans. The narrower knee and leg opening require a trimmer physique though. Be sure to have them hemmed at the right length — very little to no break looks right. Buy these in poplin — a very light fabric that I think of when I think of “chinos” — and you may tolerate the heat of summer better in the trimmer cut.

(Polo Ralph Lauren. I like them, aside from the embroidered polo pony logo at the right hip.)

If you are lucky enough to find vintage khakis, you can always have them pegged. Start at the waistband. It’s a matter of taste. And of your physique. Wear what looks good on you.

Now, about shorts and desert boots…

7 thoughts on “Dusting Off the Khakis

  1. In these casual times, I cannot think of a more versatile, serviceable, flattering, classic pair of trousers. And, they are such a refreshing change from souped up, tampered with, over-distressed, appliquéd jeans. With their subdued military overtones, almost negated when worn with an oxford shirt and civilian shoes, it is a classic male look. For hot summer days they breathe and are so very comfortable (no starch on dog days), but always look civilized. The perfect marriage with khakis is with the tan suede dessert boot you mentioned, or Clark’s Wallabees. Starched, they go nicely with a sports jacket or blazer. Beat up, worn with sneakers and a t-shirt, they have a cool, 50s “beat” vibe. In the right circumstances and appropriately accessorized, they have a wonderful, sub-tropical look. Like the blazer, the trench coat, and the aviator jacket, they have a serviceable military precedent that has continued to influence means’ fashion for decades without any sign of waning. Khakis? Couldn’t live without them!
    Square with Flair

  2. Dear Mr. E — I will now commence to shameless BEG you to write about how khakis should be tailored at a gentleman’s rear! This topic has once again reared (LOL!) its ugly head here at Rosemary Cottage. Seriously, my DH will NOT get his trousers — let alone his khakis — tailored to some degree of fit for his slim-to-non-existent bottom. Should khakis bag at the back? Does this depend on the weight of the fabric? And if so — how do you take this baggy element into account for the length of the trouser at the shoe’s heel area? And — in a less-than-serious note — my DH asks what color of sock should be worn with khakis? Kindest regards and many thanks for any advice — and we owe you a Vesper martini (the true James Bond drink of choice)

    Jan at Rosemary Cottage

  3. A wonderful article! Thank you. As a men’s style consultant, I am asked about pleats versus plain front, sock color, and pant fit nearly every day! I laughed out loud when I saw your article and later read Mrs. Jan’s comment. Many wives complain to me in the same manner that dear Mrs. Jan has to you! Will you permit me to share my recommendations? I would love to hear your reaction to them. Socks: in general, when a man wants to look polished and elegant (versus statement high fashion), sock color should match the trouser color. This helps elongate the legs and ensure the line isn’t broken when the man moves. (the line runs from his neck to his toes-anything that breaks the line visually is usually an unattractive distraction). The saggy derriere Mrs. Jan is referring to is what we call “diaper butt” and she is correct that the lack of a large rear can cause the hem to fall too long at the heel. My husband is a very slim man and has this same problem. Slim fit, plain front pants help mitigate this since there isn’t extra material from pleats to hang in the back. The best option for her DH is to go to a tailor and have the back darts taken in. These are the ones right above each cheek so to speak. A good tailor will know exactly how to do this, to lessen the sag without causing a pucker. This will also raise up the hem a bit. If it’s still too long during pinning, the hem should be altered too. Khakis should only have a 1″ break at most. Denim is usually longer and more forgiving. Thank you again for such an elegant blog. I always look forward to reading it!

  4. Hello Jan, khakis, like all trousers should fit well. That said, without seeing what the DH looks like in his khakis I couldn’t tell you what the tailor needs to do. Center seam in? Shorten the rise? etc. Some of the alterations are more expensive than others (does the waistband have to be taken off and then resewn into place?) Really, it’s a harmless operation for the customer. The tick is convincing him that he will look better for it. Anytime I’m told that I look like I’ve lost weight I reply “I have a very good tailor…”

    Ms. Bruckner, thanks for the professional opinion! It is most welcome. the break over the instep of the shoe is always a personal thing. I used to wear a very “fast” long break on tailored trousers. These days I opt for the mid-Atlantic solution which is the slightest of breaks, perhaps less than that 1″. “I grow old/I grow old?I shall wear the bottoms of my trousers rolled.”

    In regards to sock colour. Yes, I typically match the sock to the trouser to continue the line as you so rightly say. There are exceptions. As Mr. Storey points out in his book “The History of Men’s Fashion” red socks never fail to cheer one up. I will also look for compliments to the trouser pattern opting for white pindots on navy to contrast a navy chalk stripe suit. Horizontal stripes are also very unusual. A sock a shade lighter than the trouser will call attention to your feet and looks good in summer in particualr with greys. (Fred Astaire wore lighter socks so that people would watch his feet. He was a dancer after all. There are some accounts that say that Cary Grant always wore a tan sock to mimic a tanned bare ankle. I believe that to be urban legend. Grant was the master of creating the long unbroken line that lead directly to his perpetually tanned movie star face.) Finally, always choose over the calf socks (that is “to the knee”) unless you are wearing shorts or playing a sport when crew or lower socks are acceptable.

  5. How wonderful to hear from you both!! Many, many thanks for the words of wisdom! And from your words — it seems that DH will be making a trip to the tailor! This may involve the “juice of a few flowers” but nevertheless — the deed WILL be done! So far — the mutterings have included “it is NOT my fault that I have very little bottom” My reply: “Dearest you’ve always had courage — it is a simple fact of genetics that your gluteus is NOT maximus” Does anyone remember when a man had “bottom” — he had “guts” LOL!

    Jan at Rosemary Cottage (brewing up a few juices now)

  6. Love the Army khakis. Such a great cut. Found a Army Surplus store (behind the Port Authority Bus Station – how fitting) who has brand new Vietnam issue khakis. $50 a pr. I walked out in a huff but may have to go back after seeing yours.

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