Flaring Out

These still count as wide, right?

Despite the idea that I retain my clothes and that certain vibes repeat themselves, I am fully aware that taste in classic menswear (or at least the expression of it) is subject to change. It’s actually quite nice to know that things are not as static as would be expected, that my expression of what I put on my body can be varied! After all this can be due two things. Firstly, I’m young and still growing! Secondly, I’ve always been into menswear as an aesthetic exercise, something that when taken with the first point is subject to moods and volatility. Just look at my pants essay or even my entire menswear history thus far.

Embracing these moods as a natural occurrence has been the theme of my content lately, whether its something as abstract as seeing the characters I reference when Dressing Cinematically, knowing that some items just don’t have alternatives (like Barbours and Paraboots), or that there is no big deal in Standing Out. What all of this has taught me is that there is no space for style-agnostic approaches. In my life, it’s more fun to be intentional and pointed toward a POV.

This is probably why everything I wear seems to have some sort of aesthetic lean or reference. My trousers and jackets are fully proportioned. My loafers have a low vamp. My sweaters and sweatshirts are short for high waisted pants. My shirt collars are long, whether they’re spearpoints or OCBDs. My ties might have some standards like repps and solid knits, but you all know I have a penchant for abstract geometrics (which some might argue is quite dated). I embrace the aesthetic POV of my clothing, especially since to most people, it just looks like “normal” menswear clothes. Its all for my enjoyment anyway!

I’m saying all of this to provide a bit of background to explain two things. One, I think I’ve gotten rid of most of my “slim-straight” trousers (this includes my old flat front ones) that I felt were too modern to work with my normal clothing (you’re welcome Jay). And second, I’m starting to embrace flares.

You heard me right!


To be clear, I’ve always appreciated flares (bootcuts, etc). One of my prized 1930s suits (that I quickly grew out of once I graduated college) had a flared leg, as those types of legs were common for youth/collegiate/novelty suits of the era (which I believe inspired a lot of the 60s/70s silhouettes). Even though it was different than my other vintage pants, I still enjoyed them heavily. Flared legs are just so damn cool. Both in an “I like them” way and “they already are cool“.

Like everything else I’m into, a flared leg has an intentional aesthetic. Unlike my typical full trousers which provides slouch, a flare provides pure sex appeal in a trouser, akin to the effect of a wide, sharp peak lapel, a narrow waist and draped chest, or a structured shoulder (perhaps there’s something here about how math or specifically angles is erotic). Both the flare and the full, pleated leg are pointing toward something rather than trying to vie for the middle ground of agreeability. The flare also makes an extra point of interest to an other wise “boring” top block. In other words, the flares make a flat-front trouser more interesting; it’s an alternative to pleats!

Granted, most flares are really close to being a classic straight leg that is moderate at the thigh, but instead of tapering from the knee down as most modern trousers do, the grade reverses and widens ever so slightly, resting as shivering break on the top of the shoe. This combined with a high rise just creates a very attractive leg line that injects interest in the bottom half of the outfit. Who knew that trousers could be expressive in ways other than design/cloth (military/work, patchwork, etc) and simply being full vs. slim?

Obviously there are a variety of different ways to do a flare like a boot cut, where most of the leg is quite slim to begin, or a bell bottom, where the thigh is very slim and the flare is very big. I personally prefer a gentle flare, one that is just enough for some interest. Maybe that’s my inner trad, unable to do anything too crazy; it’s still gotta work with my existing wardrobe after all!

The tapered leg just doesn’t work for this. It needs a flare!

Because fuller legs fit my existing style more, they were always my priority when buying vintage or doing custom; I never really made a big point to collect flares specifically. After all, I spent a lot of work figuring the right measurements to send to Atelier Fugue and Hall Madden to get the right leg silhouette I had always loved from 30s/40s vintage tailoring just in the fabrics I wanted. I also collected second hand Levis and milsurp and workwear pants to get that full leg in RTW (as figuring out custom is a complicated algebra). But now as I’ve gotten a lot of what I’ve wanted for the “core Ethan look”, I have bandwidth now to appreciate and dip into other things (like flares).

And like with Paraboots and Barbours, I’ve now learned that the only way to get the specific look is to, well, get that specific look—there is just no substitute! Just look at the outfit above, which is clearly inspired by Husbands. It’s not bad, but it reminds me of Old Ethan, where I’m trying to use agnostic pieces (namely the chinos) to do something so obviously pointed in something specific. Flares would be the best partner to express my interest in the 60s/70s, especially since they provide so much attitude to the bottom half of my outfit. I was also inspired by John and his Paris Fits, where he has been using flares to great effect.

Don’t get me wrong—this is not change in a purge-my-closet way (my heart still lies in elements of Esquire Man and Trad) but to simply edit out what I perceive to be as agnostic and to embrace intentionality. And perhaps most of all, to take something new and add it to the canon of my style. I wanted to wear flares my way. Maybe I truly have gotten sleazy over the years.

Consider this a true follow up to my essay on 60s/70s style.

I’ll admit that Albert was an influence….
But real heads know that Warp was the OG.
Husband’s is the best in current inspo for flares in more “formal” combinations.
Natty Adams.
Husband’s again.

It’s a little funny that my first foray into “new” waters was through a pair of khaki flared chinos, a rather inoffensive ways to do the look!

I found these flared khakis at Joyride Vintage, which is one my favorite SoCal shops. I had tried on a few flares before, but this was the first time one actually fit me! They are high waisted, made of a lightweight cotton (might even have a bit of poly), and feature that gentle reverse taper I talked about earlier. The effect of the flare to me is subtle and yet makes all the difference! Its actually much more flattering than the tapered pair I previously had; I actually gave those ones to a friend who wears agnostic-business casual clothing as everyday attire; I’m glad they went to a good home!

The funny thing is that despite menswear’s reinvigorated interest in the 60s/80s, true vintage pieces are still quite cheap, at least in my experience with these. Joyride had these for a very affordable price ($40), as they had been sitting on the rack for a long time. Apparently people prefer full suits to separates and if they are getting chinos, they’d want either khaki Levis, Dickies, or milsurp. It worked out for me as a great entry point to seeing if I could really do this whole flare thing. And thankfully I was right!

Even though I’ve made a name for myself in wearing variations of 30s-60s trad clothing, I’m surprised how easy the flares fit into the my wardrobe. The best part is that they can come across as just normal khakis with a twinge of attitude that enhances an outfit rather than distract from the other elements. I know they work seamlessly with variations of ivy-trad, turning it into a specific look (think a late 60s youth who dresses sober). As you’d expect, the flares are also good with tee shirts and rayon shirts! They work as a great foil to my military chinos which are big and wide, mainly worn to slouch around rather than express a sexier attitude.

It’s like they were made for me, perhaps even waiting all this time for me to “discover” them. It’s not intimidating at all; in fact, wearing them even gives me confidence, being perfect for that Going Out attitude I’ve been cultivating as I…go out more often. They couldn’t have come at a better time.

In terms of fit, I actually like them. I used to be quite self conscious of my larger thighs, which are always quite visible if I’m not wearing a pleated, full cut trouser. Here, the slimness in the thigh is nice, as it comes in and then back out for a dramatic shape. In fact, wearing them more has helped me understand that perhaps I don’t need that much room in the thigh as I originally thought; that’s why I’m considering taking in the thigh (slightly) for some of my newer trousers in order to “equalize” the entire leg.

They look so normal….from the knee up!
Ivy-trad but make it sexy!
I like it with sneakers!
I do like flares with a jacket. I don’t think those tapered chinos (or my military ones) would’ve worked as well.
This is how it is best worn.
From here they look like regular flat front pants. The true beauty lies below the knee.
From a fun take on a spring look…
…to Going Out! (Technically this was a kickback so it would be staying in).



The flare gods provided yet again when I came across these USN dungarees at the Rose Bowl Flea only a few weeks after I got those khaki flares.

Sold by a curated vintage milsurp seller for $150 (I don’t know if these are true vintage or repro), these were hanging up on the stall, proudly displaying the patch front pockets, the slim waist, and the flared leg. These had a much wider leg opening compared to my khakis and were honestly a little bit intimidating at first glance. I almost passed on them until MJ and Adam convinced me to at least try them on! While they fit me fine, the silhouette and vibe was different than what I was already used to: the waist and hips were snug, providing a straight line to the knee and then immediately flaring out in a big way. My friends convinced me that it was a good buy, citing the fact that they break perfectly over the shoe and that I had already given MJ two of my slimmer jeans I just didn’t wear anymore.

One might be daunted by the fact that these are dungarees and not regular flared jeans. I know I was! The patch pockets and flecked denim definitely exudes a lot of character on top of the already wider-then-normal flare. But I got over it pretty quickly. Maybe I was thinking of Spencer who has his non-flared dungarees serve as regular jean alternatives. What truly helped was Forced Versatility, here I thought to myself “fuck it, these are denim flares at their core, so why not rock them”. And so I did!

The best part is that like other workwear or milsurp, these have broken in incredibly well. Now they wear so soft that I wear them more than my regular 501s. This probably points to them being reproduction rather than true vintage but I don’t care; they’re great.

Like most of my trousers with pointed aesthetics, I find no issue wearing these with whatever I want. OCBDs. Ties. Boots. Loafers. It’s honestly a no brainer at this point. Like my khakis, they definitely provide that sex appeal, especially when worn with a jacket (to cover the rugged detailing at the fly and pockets). They certainly are different than a regular 501 or workwear jean due to that difference; swapping the dungarees in when you need attitude is now a regular occurence when crafting an outfit. I think you can tell that in the photos I’ve included.

Close fit on the hips and thighs.
But then they flare out as you get lower.
So much attitude, even with simple fits! That’s the appeal of flared trousers— they make things interesting.
I love the way the flared effect is still visible even when when sitting.
The flared dunagrees add pizzasz to this suit-alternative.
Leaning into the 70s a bit more here with a striped tee and wallabees.
Flares turn a simple open OCBD + sportcoat look into something with an edge.
This is how its done. Expect to see this concept repeated!
Told ya.
Still nice to wear with a tie.

A fringe jacket just kinda makes sense.
Looks good for a 70s ivy casual look.
Oh yeah, I got some brown ones!

Before you ask, no, I’m not sure if I really need any other flares. To be fair, they were both acquired pretty affordably that I could conceivably have room for more, like ones in mid grey or dark navy if I wanted to play into the business or formal aspects of sexy classic menswear (that we see from Husbands quite a bit). Would I get a flared suit? Maybe! But that would be further down the line as well.

I’ll add to this post if I do add to the flare collection, but don’t hold your breath; I’m trying to save money for other things!

What I think is interesting is that even after all these years, these two flared pants still coincide with my desire to have a pointed aesthetic across my clothes. I’m lucky enough to have a context where there is no need to have an “agnostic style”; the fun lies with being intentional. With these two flares, its empowering to dip my toes ever so slightly into the sex appeal of classic menswear, which is something that I never thought would apply to me. I’m used to slouching around in my big pants.

Ultimately, I feel like they have added new life to my casual style, as they are pointed in something specific. They aren’t just regular ‘ol jeans or chinos. These are flared. They’re interesting!

Perhaps all those drinks with bold friends is the key to finally embracing the flare. You can’t just write about the vibes; if you really like them, you’ve gotta wear ’em!

Thanks for reading! Don’t forget that you can support me (or the podcast) on Patreon to get some extra content and access to our exclusive Discord. I also stream on Twitch and upload the highlights to Youtube.

Always a pleasure,

Ethan M. Wong

Big thank you to our top tier Patrons (the SaDCast Fanatics): Philip, Shane, Austin, Jarek, Henrik, and John.


  1. Pingback: Trying Out Flared Pants « Fashion
  2. jasonpwrites · August 15

    Thansk for this article. However, the pic with the caption: “IMG_5565 The tapered leg just doesn’t work for this. It needs a flare!”

    I disagree – that is the best look on the page! Absolutely perfect fit.


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