Fun Pants with Tailoring


It’s time to get even edgier and wear some fun pants with tailoring.

Man, I’ve certainly been on a kick lately, huh?  Suit-Adjacent casual wear, wearing black, raw hems, it just never seems to stop. I don’t want to say that it’s because I’m bored of classic menswear (as I find all of these on the same fashion plane), but rather, always finding ways to reconcile my slouchy-dressed down attitude with this style I’ve come to enjoy.

This theme continues with what I’ve dubbed “fun pants“, which really just means wide legged trousers (usually military or workwear themed) with cool details that make them an interesting (if not subversive) match for tailoring. The concept never really meant the use of checked or pinstripe odd trousers, as I never really was a fan of that; it’s mainly the rugged details that appealed to me. Since the trousers are the “star”, the trousers are mainly worn with muted/simple outfits, so there isn’t much use of crazy pattern mixing to be found overall.

As you have probably noticed already, I’m no stranger to wide leg trousers in general.  It stems from my past as a collector of 1930s-1940s tailoring. However, when I got into classic menswear as everyday style, my trousers are largely trimmer by comparision.  No, they aren’t Topman/H&M skinny (they’ve widened considerably through a long trouser journey) but they’re more in line with Drake’s or the Armoury  (just under 9″) rather than the 10″ of a true wide leg.


I still wore wide legs in modern outfits, but as I noted in my Casual Ethan essay, it’s much more slouchy as an overall vibe. Just look at the outfit above: chore blazer, severely unbuttoned shirt sans tie, and wide seersucker trousers cropped high above wallabees.  It’s not exactly a modern retelling of classic 1930’s style; perhaps I was too concerned about looking like a costume.  The vibe exudes what I loved about tailoring, but done in a way that is decidedly casual.


Of course, I always liked the idea of wearing wide leg trousers with regular (tie-wearing) tailored attire.  I simply didn’t have many trousers that fit the bill (most were closer to Stoffa aesthetics) until I got some wide leg chinos from SJC.  Other than those inner thigh issues, they were perfect, melding well in my everyday attire.  I personally found that they worked best with soft shouldered suiting; it leans into the slouchy look and contrasts against the extended/padded shoulders of period attire.  In other words, it’s a great Ethan vibe.


I’ve only had the trousers for a few weeks, but as you saw from that SJC revisit, I have worn them quite a bit. I would be remiss if I didn’t still feel like something was missing. These wide leg chinos did get the job done (and they even make me consider commissioning some Scott Fraser wide trousers), but they were missing some extra personality.

Of course, that’s when I start gathering inspiration.


Bryceland’s will eternally be a source of inspo for me because they really put what I’ve been thinking into practice.  One thing they’ve done in particular is the use of non-traditional trousers in classic tailored fits.  This meant more than selvedge denim, but  rugged military chinos and crazy olive chinos.  It’s not “the right” choice, but it’s fantastic and really separates their outfits from it’s formal connotations.

Again, we see how the wide leg plays into the looser overall fit of their shirts and jackets, especially with their preference for  extended/soft shoulders.  But the military/workwear details add something new: it’s not subversive simply by silhouette but by details. There’s even more “wrong” by wearing something that is definitely not mean to be worn with a sportcoat or tie. But that’s all a part of the charm.

In general, I think that this is almost a retread-of-sorts of Casual Ethan’s approach, though done to stay within the realms of classic menswear.  Instead of  approximating formal-ish vibes with casual clothing, this is about using alternative casual clothing to dress down an otherwise formal outfit. It’s basically trading your plain olive chinos for fun military ones.  Or using work trousers instead of denim jeans.  It’s not totally radical as a whole (as these outfits still use ties and jackets), but I see it as a definite companionother side of my Casual Ethan attire.

Military khakis with a crisp DB? Hell yes.
I’ve been thinking about this Kenji fit ever since I saw it two years ago.
Denim trousers with a classic chambray and navy jacket.
Painter vibes with those stained chinos.  It really dresses down the otherwise ivy-centric outfit.

See, it’s not simply about using wide legged pants, but rather the details of these “fun pants” that make it an interesting outfit.  For example, khaki chinos are a classic piece in menswear. In most cases, they’re kept nice or “elevated” (think Ambrosi pleated chinos).  If you go with military chinos instead, you get a heavier cloth that is prone to wrinkles and stress marks; you also get a more rugged finishing and the use of simple rolled cuffs instead of permanent turn-ups.  These things contrast against elegant footwear and well tailored jackets to provide an easy-going vibe that isn’t the clean prep-ivy look that most men default to.

A natural extension of this when you go with even crazier pants.  The guys at Bryceland’s are fond of olive HBT chinos, but not in the normal style or even the similarly common baker boy/OG-107s.  Instead, they like to wear vintage and reproduction M-43s which trade the traditional seam pockets for flap patch pockets on the hips.

That detail makes the chino instantly stand out as a casual piece, but it doesn’t stop Bryceland’s from wearing it with tailored pieces.  You”ll note that it’s not done with spread collars, oxfords, and jacquard ties, but with things on the “casual” end of the spectrum like tweeds jackets, OCBDs, chambrays, and repps.

I know that a few years ago there was the “tailored cargo pant” trend, but in those were always so slim, making them look too try hard in my eyes.  Here, the fun military chinos are practical, rugged, and loose fitting, which makes it fine. The study cotton twill or HBT also makes for a better look than the shiny nylon of modern cargo pants.


Wearing fun pants with “classic tailoring” also has an inherent Japanese influence. Unlike America, Japan doesn’t have the same heritage and tradition for classic menswear; by that, I mean that they don’t really have (or follow) crazy rules of what must go with what and what shouldn’t be worn with what.  As a result, you get lovely mixtures in styles and colors by a lot of Japanese people (or dressers who follow that aesthetic) done because it’s simply the cool thing to do. Bryceland’s does it really well, but you can see that a few other guys, like the Beams+ gentlemen above, do it in their own way.  In most cases, its still done in an ivy/trad context, which is what I prefer.

It’s not about what is “correct”, but rather if it’s a good style move that makes you happy. We actually discuss that phenomenon in our podcast episode about rules, but it’s mainly that punk/edgy mentality.  Yes, you can always look sharp when following the correct pairings in menswear, but it’s the weird choices you make that result in great personal style.

My friend Kota from Japan.
Shinn, from Kamakura.
Great casual Ethan on center left, but Audrey does it really well in a dad-ivy look.
Classic use of flannel jacketing, denim shirting, and the miltary chinos by Cody Wellema.
Doug in vintage European HBT trousers.

Now despite not being a sartorial dresser, I have to shout out my pal Doug.  He’s a big fan of vintage milsurp clothing and one reason why Spencer’s style has evolved so much in the past year.    I credit him with introducing me to a lot of “fun pants” in the short time I’ve known him and helping me find a few for myself, despite the fact that I would wear them radically different than how he does it.

It was really nice seeing them in person rather than on pictures from my Japanese friends or on the Bryceland’s boys.  It really gave me ideas on how I would do it once I was able to score a pair.

Camo pants on Will and M-43’s on Doug.

On Us

I’m sure that you can tell my philosophy on “fun pants” by now.  They’re rugged and utilitarian with a workwear/military background with a wide fit. It’s best worn with ivy-trad tailoring with hearty fabrics.  Honestly, I don’t really wear “fine”clothing anymore (sorry brocade ties), so that made the introduction of these pieces rather easy.  The pieces flow together well for a subversive take that is heavily influenced by Japanese-Americana and Brycelands.  If that wasn’t obvious already.

Overall, the theme is basically a continuation of my philosophy with raw hems. Not only is that because ivy-trad works with nearly everything (and can be messed with), but because the use of rugged/faded/utilitarian military clothing is subversive and a bit punky (that doesn’t rely on wearing black). Remember that I don’t dress by following the rules; I dress because it’s fun!


Let’s start off simple shall we? Here we have a pair of true vintage 1940’s WWII chinos, copped for $35 thanks to Doug’s keen eye at a flea market.  They’re flat front with a high rise and wide leg, which make them different than my slim-straight J. Crew ones.  While I have owned pleated military chinos before, I think I prefer these better due to the fact that is less of a yellow-khaki.

The flat front makes them a bit more versatile to move between casual and “formal” looks, but I’d be remiss if I didn’t gush about the length and width. I’ve wanted to have rollable chinos for a long time that weren’t tapered, and these WWII ones were perfect for it.  If you recall, the repro officer chinos were slightly tapered and feature a permanent turn-up, which makes them only suitable for more formal looks.  Now, the WWII chinos can slide between workwear and Japanese-Americana tailoring with ease.

The chinos were only rolled up for one “cuff” and are perfect.


You can really see how rugged they are, from their finishing (they actually faded a bit after I washed them) to the fact that they’re unable to hold a crease; I like that for these easy-tailoring looks.  Nothing about it seems stuffy to me or that I’m trying to “dress up”.  Even so, I chose to go with a chambray spearpoint workshirt to emphasize the casual nature of the fit and finished it with a well faded/worn foulard that I thrifted years ago.  You also can’t forget the white socks and suede tassel loafers, the latter being the main dressy part of the outfit.


Next up, we have a real life pair of gurkha trousers!  These were found by Doug during one of his random buying travels, which he then sold me.  Like I’ve stated in the original gurkha shorts piece, gurkhas have an interesting vibe.  Without a belt loop, they provide a wide and clean waistband, but the complicated double closure adds some oddness that adds some allure.   The pleats help push it toward tailoring, but the wrinkly twill plants it firmly in casual land, that is until I wear it with my clothing.

I’m not sure how old these are or where they are from, but they certainly are a fun pair of pants.  In addition to the normal side pockets, these also have flap thigh pockets, making them a bit like a pair of cargo pants.  Unlike the WWII chinos above, these required a few rolls to get to the right length, which help keep the casual vibe going.


I actually mainly wore them with tee shirts during the summer (most famously with a Star Wars one), but I finally bit the bullet and put it with some early fall attire.  Navy hopsack jackets are a no-brainer, so I pulled out my epic dark brown Ring Jacket Balloon coat. I leaned in further into fall with a yellow check spearpoint and a bold repp tie.  In retrospect, I could have gone with a chunky derby, but at the time, I felt that a lazy penny loafer was right at the time.  It’s actually one of my “style rules” to default to loafers whenever you’re wearing something fun.

It’s pretty much a fun look that most people won’t notice, as the jacket’s quarters cover the fun waistband of the gurkha pants.  On the surface, it’s just a classic olive + brown look, but as always, details matter.  That’s what makes it a fun outfit!


These blue slub cotton worktrousers were actually my first “fun pants” I ever bought (during one of my early Rose Bowl fleas), but I never really had the draw to wear them out until recently.  Like the gurkhas I have no idea on the age or origin.  As you can see they are a bit odd to wear, being different than the pleated denim pair worn by Ethan Newton or the HBT worn by Doug both earlier in the article. Being flat front, they actually have some similarities with the WWII chinos, just with a few details changed.

Again, I didn’t want to default to my slouchiest jackets, so I actually took the opportunity to challenge myself.  In a nod to Bryceland’s (who have such great Dalcuore pieces), I wore my United Arrows mohair jacket, which boasts a great blue-grey check.  Instead of an OCBD (which may have been a better choice), I had my blue stripe spearpoint; a black knit tie was done to tie it back to ivy, as well as to echo the black penny loafers.

Now that I look at it, it’s a bit monochromatic, which isn’t something I do with tie-wearing outfits, but it’s quite nice! I think that the trousers help slouch-ify the jacket, which definitely is one of my more “formal” pieces due to its slightly stronger shoulder and overall shape.

Pockets galore.  The one on the leg was probably meant to hold a hammer.

The major point of interest is the cloth.  The slubby cotton is certainly a weird shade of blue (almost periwinkle at times), has flecks of white, and a bit of fading all over, making them a perfect candidate for “fun pants”.  The trousers are incredibly lazy, unable to even hold a single cuff; rolling them more would make them be too short.

I know that these trousers have suspender buttons, but I’ve been too lazy these past few years to even put them on (unless it’s with evening wear or a 3PC suit).  A simple belt is fine, though I do wish I had a more rugged belt.

Lazy cuffs that come undone almost immediately.  That’s fun!

Because they do feel a bit like fleece, these trousers are probably best worn on milder days, just for comfort’s sake.

Honestly, I prefer this outfit over the grey mohair one, just because it’s simpler and more ivy.  The monochromatic use of blue again is different for me, though here the emphasis on darker colors works better with the trouser’s odd shade. I felt that just having the jacket was too boring, so I supplemented with a cotton sweater vest.  I know that the layers are a bit incongruous with sockless loafers, but sometimes you gotta live life on the edge!

A simpler outfit inspired by Spencer, utilizing an unstructured vintage seersucker.

Edit: 12/31/19

So I eventually got to replace those work trousers with more traditional cotton HBT ones. They’re a vibrant workwear blue, but I find them just a tad more interesting than the fleece-y ones above.  I like the drape better (similar in fit to the WWII chinos) and the fact that there is extra length to do at least a good single turn-up is more than enough for me.  They hem hovers over the penny loafers in a way that approximates a regular tailored chino!


It works well here with a rather minimal, blue-centric ensemble, with the work wear accented with a chambray spearpoint. think that putting it with anything striped or too wild might be too distracting due to how saturated the blue work pants are. I may not be able to wear it with much in terms of tailoring, but I know they’ll be a welcome addition to future Casual Ethan fits in 2020.

I was right- I do wear them in 2020.

Now we get to my babies, my favorites, my most fun pair of pants: the US Army M-43 chino. Like I said earlier, these WWII era pants are made from HBT and feature flap pockets rather than the normal ones we’ve seen on the previous ones.  I actually started to get interested in them after seeing the Bryceland’s reproductions, but I managed to snag a true vintage pair from a vintage sale that Doug invited me to.  My gurkhas were initially going to be my go to “green military trouser” but these take the cake.

The fit of the pants is absolutely stellar. Super high rise, roomy leg and an extremely wide opening, much more so than the WWII khaki chinos.  Even though I definitely like pleats on most of my trousers, the overall slouchy silhouette makes them incredibly versatile and wearable.  The green is a great subtle shade that is much less saturated than the gurkhas or even typical vietnam-era chinos. It’s a sobering approach to “fun pants”, but again its the details that make it fun!


The idea behind fun pants is that they really help add character to an other wise normal outfit.  That’s definitely the case here as it’s worn with a navy hopsack and repp tie.  The shirt is a chambray workshirt, which leans into that rugged casual vibe, but an OCBD would have been just fine. Hell, I’m excited to wear these with my tweeds in the coming months, if it would only get colder!

Obviously this would look great with a tee shirt, but I love the challenge of wearing them with tailoring.  In any case, no one should be able to say that this is dressed up, because you’re wearing literal cargo pants with big ass pockets.  Wearing them definitely accomplishes my desire to look sharp but slouchy, all at the same time.

Pairs well with a brown checked jacket!

While Spencer has been a big proponent of milsurp, he hasn’t had many chances to wear fun pants with tailoring. His main pair of fun trousers was a well faded pair of OG-107 pants that have a rich green (more so than the ones I own) and a slight taper.

Like me, Spencer keeps it firmly within ivy-trad for his outfits (though he has worn them much casually in other circumstances) and opts for chambray shirts as a go-to top piece.  It really adds character to an other wise standard outfit, which helps everything look a bit more intentional and less stuffy.


Not wanting to be left out, Spencer found some reproduction M-43’s in camo; I have a sneaking suspicion that he wanted to one-up me.  Whatever the case may be, these trousers are damn cool.   Don’t let the frog print fool you; they’re wearable as long as you wear them with other plain clothing. If you wanna do fun pants, you gotta make everything else rather boring.


I didn’t have time to include these, but paint splattered denim is fun too!

We all knew that I was going to fall down the mil-surp hole sooner or later, but I was never going to let it make me fully casual. I will always like wearing button ups, ties, and sportcoats!  So naturally, the way to incorporate my “new” love for military/workwear (thanks Doug) was to add them in as fun pants.  By that, I simply mean that they are bottoms that aren’t the traditional pleated trouser or chinos you’d normally wear with tailoring.

The idea behind fun pants are the same as everything else we’ve discussed lately, namely the Casual Ethan vibe and raw hems.  For the first part, it’s about achieving a slouchy look that replaces common menswear pieces.  AKA, you’d swap your crisp chinos for a worn pair of wide leg WWII khakis.  Or you’d trade your dark denims for wide M-43’s. It’s subversive and yet straddles the line between sharp and lazy. We can thank Bryceland’s and Japanese-Americana for providing the inspiration there, as those guys are concerned about making a fun outfit rather than following the rules of menswear.

The latter point is to basically style yourselves in ivy-trad to make sure you pull it off.  The rugged nature of cargo pants, gurkhas, and workwear cottons don’t really jive well with collar bars, sharp spearpoints, and brocades.  You can try, but it’s pretty hard to do. Even when I tried it with the grey mohair, I knew that I needed a second pass to make it right.  In any case, navy jackets + OCBDs + repps are a guaranteed way to pull off fun pants. For some reason, ivy-trad is just a great match for these milsurp/workwear pieces.

Hopefully this gives you inspiration to try it for yourselves!

Always a pleasure,



  1. David · October 21, 2019

    It’s weird seeing how trends are circular. I’m 20+ years older than you and your crew, and wide leg was a big thing back when I was in my 20s during the 1990s. I lived in Southern California like you guys and remember everything from Cross Colors to JNCO to J. Crew to the launch of RRL having wide legs. I worked at Armani Exchange at South Coast Plaza and the majority of Asian-American customers in their teens and 20s wanted wide leg jeans back then. We constantly sold out of a women’s jean that had our widest leg (probably an 18″ opening on a 30″ waist) to both women and men. I remember RRL launching in the Bullock’s (now Macy’s) Men’s Store in South Coast. It was only there a few seasons, but RRL was then carried at the Polo Country Store on the Crystal Court side (either where Sur La Table is or the restaurant diagonal from it) and picked up a wide leg jean with suspender rivets, medium rise, in a rinse wash. It was probably $80–that was right before Polo Jeans launched so RRL was at still of a more accessible price point. I wore them a few times before deciding that fit didn’t flatter me. I prefer things that fit my body shape better–not sure what shape is complemented by a wide trouser. But that is a matter of preference.


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  5. shem · December 11, 2019

    HI ethan, seeing how you are moving away from strictly or “properly” tailored wardrobes, what kind of details would you look for if you were to do up MTM/bespoke cotton trousers? E.g. flat front vs pleats, belt loops or not etc.


    • Ethan M. Wong · December 11, 2019


      Haha I wouldn’t say I’m moving away! If you look at my Ig, you’ll note that nothing really has changed. I’m just supplementing with new ideas for when I wanna get fun!

      Honestly, fun pants are fun because they’re made that way already. If I commissioned bespoke cotton ones, I’d get them the same as anything else: double reverse pleats, extended waistband, and side tabs with a wide leg and a turn up!


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