A Tailoring Experiment: Pleated Trousers

Now that we can agree that pleats are cool, it’s time to try them out.  I noted in my previous article that it is difficult to obtain pleated pants with the necessary details (high rise, slim-straight).  So when I was presented with an opportunity to try and tailor down some 1980’s baggy, double pleated pants, I took it.  If it worked out, I may have found a way to get pleated pants at an affordable price! If not, I’ll be out a few bucks, but I know it can’t be done. Let’s find out!

Off the Rack Pleated Pants

Before we get into the tailoring experiment, I just want to show you that  I do own modern pleated pants; it wasn’t my first rodeo.

I bought these pleated linen trousers from Banana Republic, to see what modern/mainstream trousers had to offer.  While they were comfortable, the low rise and double pleated feature did not look as good as I had hoped.  Even though the pants were slim, the lack of high rise made the pleats flare out at my crotch


The Experiment

After my disappointment experience with the BR trousers, I almost gave up.  However, there was some hope.  My tailor called me in to check out some pants that a client had given to him; Mr. Tran asked if I wanted to keep them for free!  I came in and this is what I saw:  a baggy, pleated 1980s monstrosity.

First Fit (no tailoring)

Even though they were baggy and much too long, I saw that these pants were high-rise, hitting above my belly button! Maybe they could be saved with some tailoring!  I asked Mr. Tran to taper the legs (7.75″ leg opening) and hem them up, to see if that would solve the problem.

Second Fitting (hemmed and tapered)

It didn’t work as well as I thought. While the ankles look great and are hemmed correctly, we all can agree that the pants look weird.  The pleats still make the hips too large, which makes these look more like jodhpurs instead of cleanly tailored trousers.

Note the wide hip area jutting out at the pleats, before oddly tapering from the knee down.

Perfect hem, but still weird in the upper leg.

“Pegged” pleated pants have been popular before, as a fad in the 1950s, but that’s not what I wear on a day-to-day basis.  I asked Mr. Tran what he would do next in order to make my pants look good.  He said he could try to take in the crotch and the thigh, but he’d have to redo the pocket.  Even though I felt that this experiment was getting more and more expensive, I had him do it; I really wanted to see if this could be done!

After another week of waiting, I finally had the finished result..

The Final Result


Mr. Tran freaking did it. He was able to slim down the thighs for an overall cleaner look!  They may not be Ambrosi Napoli trousers, but they are visually close enough!  They even have an extended waist-tab, which is a pretty Italian detail.



They are very roomy in the thigh area, but I love it.  I have big thighs, so having double pleats really helps me out!


Going Full Italian


When you combine pleated light-weight trousers with a deep polo and white linen jacket, you’ve got summer Italian style down.  The propped collar isn’t necessary, but works for an Italian inspired look.  Plus, that’s how it was done back in the 1930sdone back in the 1930s! Personally, I find that it helps keep your neck cool!

The outfit was partially inspired by this outfit by Alan See of The Armoury.  He is pictured left, wearing almost the same out! I simply swapped his full button up for a polo!


Shamelessly inspired by the fantastic photography by the Armoury.


Even my jacket has a pleat!  This particular style of pleat is called a bi-swing, and is used to give more motion to the wearer.  This detail, combined with high arm holes, allow the wearer to move around without constriction or distorting the shape of the jacket!  It’s a cool detail that hasn’t been done in over 50 years.  If you’re wondering,  this piece is a full linen, vintage 1930’s jacket! It is completely unlined and lacks any shoulder padding. making it perfect for a casual sartorial style.  You can see where the Italians got their inspiration!


Overall, the price of the alterations were $40; this is much cheaper than going to Ambrosi Napoli for his excellent hand-made trousers.  While the alterations were cheap, it is a fact that I received the pants for free.  If these were typical pants I’d find in a thrift store, the overall cost would be around $60 bucks, assuming the pants are below $20 at Goodwill or some similar store.

If you want to attempt the experiment and try to get some pleated pants yourself, please be wary.  As I’ve stated in my previous article, a majority of pleated trousers in the market are not slim or high waisted.  More often than not, they will look like this (which is pretty close to my initial fitting:

If you happen to find some, please try them on first and see how high they go on your waist.  If they’re cheap, bring them to your tailor and see what he or she can do to make them look good.  As we’ve seen, simple tapering may not be enough to save it.  If you buy from a department store (Macy’s, Sears, etc), see if they have a return policy if your tailor says that they can’t do anything for it.  Just don’t make any alterations yet!

Your experiment may not even be as cheap as mine!  I’ve known my tailor for over 2 years now and have developed a close relationship with him.  I was very confident in his work and would’ve paid him regardless if he was able to save the pants or not!   It may require more work at your tailor or your tailor may have different prices, so please be wary of that before you think you can tailor anything you want.

I will say that it may be worth it to get an awesome pair of pants.  It’s a gamble, so if you have the money, I say go for it!  I did it and came out with my new favorite pair of trousers that can be worn with a tie or casually with a polo!  Let me know if you try it for yourself.

Always a pleasure,

Ethan W.

Street x Sprezza

Photography by David W.  




  1. sean · August 5, 2016

    this is a sick accomplishment. sick pant!


    • Ethan W. · August 5, 2016

      When in doubt, ask a tailor! Mr. Tran has done some great things for me!


    • gipsonbachman · September 10, 2019

      Love these pants, Mr Tran did such a great job. It’s so hard finding a good tailor that is willing to make your vision into reality. Would you mind sharing his contact info? I’m in Burbank and so desperately want this kinda of relationship with my tailor. 🙂


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