An Appreciation for Weird, Niche Vintage Menswear

Menswear wasn’t always about being “timeless”- it was also weird. And I love it.

Well some of it.

Like always, be sure to listen to the conversation Spencer and I had on the Style & Direction podcast before reading the essay! We go into much more detail about specific niche vintage pieces we like. Then you can read my written appreciation for the ideals behind it and peruse the images.

This top is weird, but I love it.

Man, my style (and the blog) has gotten quite different over the years. Now I get comments being called “the beret guy” or the “suit guy” when for a long time, I used to be blanketed with “dapper” or “vintage” as a moniker. This is mostly because my style gradually taken on a contemporary (or in some cases, post-modern) spin, making a much more nuanced take to classic menswear than just being period-accurate. The fact remains however, that a lot of my style still references a lot more vintage than modern, even if the pieces themselves were made in the past 3-5 years. My archives are also filled with much more vintage inspo than modern ones- I always find myself going back to vintage, even if it’s just to look. It’s about pulling the vibes, you know what I mean?

After doing that whole essay on Apparel Arts and The Esquire Man I decided to think about why that is. After all, going period accurate isn’t exactly what I’m about anymore. It’s “more” than that- a love of details perhaps? Our conclusion was that he and I share a general love of history combined with a passion for clothing. In essence, it’s just cool for us to look at clothing within our narrow POV that doesn’t exist anymore. It’s niche and special, especially when we make it work in a modern context.

There’s just something intriguing about garments or details that aren’t common. I’m sure this sentiment applies to a lot of thing in the nerdy-collecting space like rare Pokemon cards with alternative/limited artwork. From an art standpoint, it’s also similar to noticing how some styles fade over time and transition into the next, with a few either being ahead of its time or referencing something even earlier. It’s all in the details and with art (and menswear), details truly matter.

What makes our appreciation for vintage menswear even more fascinating is how these niche details apply with facets of tailoring (a term which you know I use quite liberally). Most people in the mainstream assume that tailored clothing is meant to be safe and conservative. While that’s true in broad terms, looking at AA proved that combinations and styling were actually quite creative. Granted, this was the #menswear of the day and men didn’t always follow Esquire and dress like that (though you could definitely tell the ones did). What I’m about share with you goes to show that the details of tailored clothing (and its accoutrements) were also quite wild.

The presence of these “out there” details (as well as some done purely for art or in some cases, rebellion) makes sense to me because tailoring was truly la lingua franca of Golden Era. Sportcoats, ties, and collared shirts made up most of men’s clothing, unless you were out at a specialized job or hobby. However, this didn’t mean that everything was business wear. What ended up happening was that tailors, brands, and designers would use tailoring as a backdrop for interesting details to make their garments stand apart, whether it was simply through design or to play off of a garment’s functionality or even formality level. Some of it was simply about adding in workwear or military details to piece; other times it was just something flashy, with no real functional purpose. Classic menswear, at least back then, was fashion.

Unfortunately many of these pieces were considered novel even then, which ultimately meant that not many were produced and results in them being quite rare (read: impossible) to find in person. This is why much of the stuff I included only exists in illustrations and photographs; only hard core collectors and museums have the existing pieces.

The allure of this niche vintage menswear comes from the fact that is just scarce, not only physically but in the POV of current menswear. There’s just an incredible sense of beautiful practicality and ulitarianism that seems to persevere through most of these niche vintage pieces, all with the theme of tailoring (again a loose term). For example, it wasn’t out of place to have a belt back sportcoat with pleats to ease your movement or even four patch pockets ready to be stuffed with the day’s necessities.

There was also just a wonderous idea that classic menswear should be beautiful and interesting (whatever that means to you), which lead to more elegant takes on espadrilles or decorative punches found in spectators. Peak lapels, a detail considered formal by many modern menswear enthusiasts, were routinely found on non-formal jackets- they were simply a design choice to use in conjunction with tweed cloth and patch pockets. Double breasted jackets were treated similarly, with many not following the current convention on the style. Hell, the use of belts (literal ones, not half belts on a garment’s back) is quite a decorative and interesting addition, done to cinch the waist in a flattering manner- you can see this on all manner of jackets. It’s a shame that most of it only exists in photographs and illustrations. It’s even worse when you see that even at the higher level, current menswear is still boring. It just lacks that same punch as vintage, making it a real treat when we see niche things online (or in person).

Casual wear (known as sportswear) was also much more interesting than what we have today, at least when the mainstream is concerned. Back then, polo shirts had a variety of different styles, not just in colors and fabrics, but in how the plackets and collars were designed. Some had loops while others felt more like a pull over sportshirt; a few even incorporate wide ribbing, which accentuated the waist. Overshirts (back then they were Hollywood/leisure jackets) were quite common place to wear at home, made from wools and rayon gabardines for a louche look. Tees even had variations, with a few notable ones being ribbed and mesh- a far cry from the rather simply designed 50-50 blends coveted by explore page vintage resellers.

While a few of these ideas have come back in spades (like knit polos and chore suits), there’s just something much more elegant and interesting in how the original vintage ones have done it. The Golden Era just makes tailoring so easy to wear- especially since to them, it was sportswear- something kinda tailored, but not meant for business. It’s just a shame that most of this stuff hasn’t returned. Even modern sweatshirts lack the cool features of their vintage counterparts, both in fit and details!

To most in the modern day, the of interpreting tailoring and making it interesting can seem wild. Lurkers on MFA and random tiktokers seem to comment endlessly about boring classic menswear is and yet they are completely resistant to deviations from the mean- whether they are modern or vintage. Even the #menswear world is a bit too “cosplay conscious” for them to embrace a few of these wilder details, even if it helps make the case that menswear is fashion rather than something inherently formal. It’s unfortunate people feel the need to box menswear into such a rigid space that no one will like. When you look at these fun-yet-odd pieces of vintage sportswear, you’ll know that it wasn’t so inflexible. Maybe that’s why my friends and I, or at least those with an expanded appreciation of vintage and it’s niche treasures are pretty open with the inspirations we have and the styling we prefer.

Now don’t get me wrong- I don’t think that all of these pieces should come back. Despite my love of spearpoint collars,a wide leg, and the occasional mix of rugged items, my style is rather safe. I’m not about to wear crazy perforated spectators or mesh shirts just because it’s niche. To me, this niche vintage is something different than sportshirts with droopy camp collars or a low notch lapel. It’s not about simply resurrecting them to the same degree as mislurp and workwear. Instead, these old oddities inspire me to think of classic menswear the way they did. Not as business wear or formal wear, but as clothes. Being able to play with the details of tailoring without deviating too strongly is such a cool notion. Overall it is this mindset behind Golden Era menswear that I wish would return in some form today.

Even from my earliest days of vintage, I learned that classic menswear as a conformist, safe mode of dress is a relatively new idea. From photographs of Lithuanian families to French menswear illustrations, I was exposed to so many different menswear details and garments that prove how vibrant menswear can be. Fits and silhohuettes had variations, whether it was in the shape of a jacket, trouser, or even the lapel. It was different from Apparel Art’s appeal, which to me was more about styling. With niche, odd vintage menswear, the draw was about the inherent design of vintage. My thought was that if the so called Golden Era of Menswear had fun with their clothing, why can’t we?

This is why I have no issue with wearing LL Bean Sport Vests with ties, wearing gurkhas and cargo pants with a jacket, or putting patch pockets on navy worsted suit. It’s all about keeping that “vintage” approach to menswear alive, especially when the details are already inherent in the tailored garment- it’s different than just combining rugged pieces with it. That idea of slouch? The Golden Era had it, all present in the novel/niche pieces they had, done through utilitarian design or by leaning into the elegance and fashion for fashion’s sake. Hell, this just means that to get those details, we have to continually buy vintage since modern makers (at least ones relatively accessible) don’t do it. Why else do you think that so many of my friends and readers all buy vintage? It’s the only way to get non-boring classic menswear!

Of course a few of these details are present today, though it’s just as hidden and niche as you’d expect. It turns into a fun game when you’re able to find some of these ideas scattered through menswear of different eras. Thick belts were a thing in the 1920s- they eventually found their way to casual wear later on. Quad patch pockets were common for sportcoats, fell out of favor in the 1960s, and then came back in a few Armani jackets in the 80s. Hollywood jackets paved the way for leisure suits in the 1970s. The Bedford from Engineered Garments looks like a 1910s jacket, just done in non-sartorial fabrics. Silhouettes of Lithuanian suits can be found in some avant garde takes on tailoring. The list of references to niche vintage menswear goes on!

And hell, if the so-called Golden Era was comfortable with mixing in some crazy menswear details, designs, and silhouettes, why can’t we have an expanded view on classic clothing? I’m sure they had the same spiels about looking elegant and appropriate, yet its clear that they wore Danner boots with suits, had a tie with a leather jacket, or wore a knit tee with tailoring and sockless loafers. They also had belted jackets worn casually or had some cool popover shirts to signify that they were off duty. This is what people should pay attention to, not some blogger who seems to only be concerned about transitioning seamlessly from the boardroom to the bar. Niche vintage menswear proves that menswear is an avenue for fun and creative combinations, not just in patterns and cloth, but in the specific pieces and designs themselves.

So enjoy some of our favorite images of niche vintage menswear. It’s almost like looking at the original for many things we see in modern clothing today (though with a few obvious changes). Maybe you’ll get the same inspiration I did- not to wear the exact pieces themselves but to apply that same theme of practicality and elegance in classic menswear. Approximating the vibes if you will. Or it’ll just trigger an insane thirst for vintage menswear, along with a sense of disappointment that current menswear will never be this interesting again.

Either way, the point is that even with “classic” menswear, you can still have fun with it. It’s not always about being corporate or formal! Having that expanded mindset will make menswear much less restrictive- at least for us. But more on that philosophy next time.

Podcast Outline

  • 07:47 – Intro to Vintage
  • 16:12 – Workwear
  • 30:07 – Shoes
  • 38:37 – Tailoring
  • 43:39 – Trousers
  • 48:22 – Shirts
  • 55:54 – Suits
  • 1:17:43 – Palm Beach
  • 1:27:29 – Closing

Recommended Reading

We also did a whole stream where we dive into some of the fun things Spencer and I found to prep for this episode/blog post, with special guests Aldous and Ivan!

1920’s futurist suit.
Futurist waistcoats.
Giacomo Balla.
Seems almost modern. Also check out those leather sandals!
The bottom left. Elegant, yet casual. Worn with oxfords no less!
Wide belt with a great tip.

1930’s European popover shirt in chambray. Shirts back then were cut wide with a long back, deep placket, and soft collar.
Bryceland’s even made their own version!
Spearpoint popover shirts are cool. Worn here with a Hollywood jacket which we will see later.
The 1930’s even had their own version of #menswear shirting.
Spencer has a fun western shirt with a printed design. Probably a better move to do micro patters on western shirts rather than a dress shirt.
Belted sportcoat with four pockets.
Looks like a belted jacket without lapels.
I’d wear these to the office. Wouldn’t look formal at all!
Raglan sleeves, a belt, and angled hip pockets.
A cardigan jacket?
Safari jackets always seemed too much to me. A belted sportcoat seems more my speed.
You wanna talk about wild? These are Rah Rah suits, a youth fad in the 1910s.
Ugly, but hey, it’s tailoring.
True precursors to the zoot suit.
“Regular” 1910s-20s suits that all have odd details. Back yokes, angled pockets, trim fits.
Youth suits or “jazz” suits.
Not out of place for young guys to wear cool suits!

Of course, ivy sack suits were always around.
Zoot suits.
Pegged trousers with welted on-seam pockets and dropped loops. Thin belt is great here, as well as the yoked pockets on the sportshirt.
Unlike the ones worn by cartoons and stage performers, true Zoot clothing was only slightly exaggerated. It’s kind of a look, if you ask me.
If only we had similar approach to tailoring now!
Novelty cloth was quite common place in the 1920s. Not everything was dark and solid.
Filipinos wore McIntosh suits in the 1930s. These suits were shorter in the jacket length in order to offset the usually small Filipino frame.
Horizontal peak lapels. A niche detail today.
Novelty cloth and a belt back. Having these details makes menswear a bit more fun than just business worsteds.
Apparently the 80s weren’t the only ones who did notch DB jackets. For some reason, they look better here.
Echoing Rah Rah suits, 1920s-1930s collegiate pants were designed to be quite wild. Check out that wild, naval-inspired waistband. It would be awesome to have trosuers like this.
These are fucking crazy. I know that some brands do something similar but they lack the Golden Age’s elegance (or at least the “dressy” nature of it).
European suits were always cut weird. There’s something endearing about them though.
Safe 1930s models.

Great cloth that many would be resistant to today.
Guys had fun with shirts too!
Are you advanced enough?
Wide belt, blazer, and a light felt hat.
The whole look is so good.
A 1920s jacket that has some funky details.
Crazy European lapels in the 1930s.
Dancers would wear flashy waistcoats like this. Not only is this a low, double breasted vest, but it’s got a two-tone tattersall pattern and a belt.
1950s suits with a bold silhouette. Proof that menswear always had fun with details.
Some crazy clothing here.
German suit with wonky lapels.
A double breasted evening coat? We should bring this back!
More novelty cloth.
A cool 30s sportcoat that curiously combines peak lapels with pleated patch pockets. An “illegal” mix to formality purists, but par for the course in the 1930s.
If more guys wore suits like this, we wouldn’t think of tailoring as something inherently formal. Just look at that action back, the microcheck pattern, and the bellow pockets! It challenges modern conventional menswear.
Tall collars were an interesting variation in the 1910s. We don’t need for it to come back though.
Casual details like belt backs and patch pockets were semi-common in Golden Era Tailoring. They were “casual” details that certainly make them more interesting than business wear.
Small lapels and a weird tie knot. People did funky stuff back then!
Sawtooths, hollywood waists, and a legit western suit.
More youth trousers. You see similar stuff today, but certainly not in the same vein.
Double breasted waistcoat on the right.
Quadruple patch pockets! A great way to make tailoring appear more utilitarian.
They say DBs are formal, but many in the 1930s-1940s had patch pockets.
I feel like I’d see something similar in some vintage-inspired Japanese tailored brand. A good way to get the stuffiness out of menswear. Might be fuddy, but thats where your attitude will come in to correct it.
Norfolk suit.
Bring back fun pockets on tailoring!
Quad patches with pleats.
I could fit so much camera shit in there.
It’s practical for movement, but also just a flex on the tailor.
Fancy backs!
This can’t be appropriate for business- that’s why I love it!
Now shoes were crazy. A good example of where menswear had some fun (while still being “dressy”).
Haven’t we seen stuff like this before? Yuketen perhaps?
Problematic af.
Check out those spectators! Quite elegant.
The ones on the right could definitely be Yuketen.
Spectator shoes used to be more than just two-toned- they had perforated designs!
Woven captoes.
These look like they could’ve been made by a bespoke Japanese artisan
Big belt again.
Sweaters used to be so fun.
Novelty ribbed tee from the 1950s.
Shaker knit.
Action backs were even found on knitwear.
Mackinaw jacket. Much more interesting than a plain navy peacoat.
I wouldn’t wear it with tailoring, but a mackinaw would be killer with turtlenecks and jeans. They’re basically a more interesting alternative to a peacoat….if you could find one.
I’m at least happy that knit tees are coming back.
However they lack the cool details like the cable knit designs and the contrast collar and cuffs.
This one doesn’t even have a ribbed hem!
Tees are much cooler when they look like this. They evoke a tailored vibe without being overly stuffy.
Interesting military closures on the left- similar to the ones you see on gurkha variations.
Funky German knit wear that helps bridge the pieces to tailoring.
I’d wear this entire thing today. Not stuffy at all!
Vintage sportswear is so great. Tailored brands should take notice instead of just producing plain old pique polo shirts that look like corporate swag.
Loop closure polos are the move.
That outfit on the right is so good.
Western popovers are nice too. Probably a bit trendier (in a good way).
Can’t forget gaucho shirts!
A real shirt-jacket.
Palm Beach- a cloth that just doesn’t exist anymore.
Apparently they came in more than just white/cream!
Leisure jackets. The perfect mix of a sportcoat and sportshirt. Try to remove the vintage connotations- these would be great for most regular guys out there who are tired of chore coats.
Just needs some Wranglers and roper boots.
Should Coggins get in on this?
Hollywood jackets (or more accurately, a leisure coat).
We need to bring these jackets back. Not as gaudy as a 1970s safari jacket nor as rugged as a chore coat. The Hollywood jacket fits right in the middle, perfect for a more tailored style.
European menswear, coming in clutch with the cool tailoring.
Cycling jackets are much more cooler than workwear jackets or Ricky jackets. They’re utiliarian, dramatic, and rare.
I love these jackets. They’re just so much cooler than denim truckers or military jackets. There’s something more tailored about them, though you could clearly wear them casually (without a tie).
The Sport Vest design is a good example of of niche vintage that works today. Like the other pieces here, it’s odd but serves as a fun alternate to typical blousons and work jackets. It’s “tailored” but not stuffy.
It also feels vaguely European.
Makes for a “suit” when “matched” with white workpants.
It ends right at the waist. Perfect.
Leave your Type-2 denims and A-2s at home. This is what I want.
Much cooler than a typical double rider IMO.
Modern menswear jackets just don’t have these details or personality anymore!
Shoes and jackets are amazing. What happened to vintage sportswear?
A crazy jacket. Feels almost 80s but with a better silhouette.

Cycling style.
Could you imagine a trend where men slanted their hats? Me neither.
Even if the designs are normal, vintage still did them in fun fabrics. Like could you imagine pinstripe shorts? Insane! Don’t forget to check out the popover safari shirt on the left with a clasp placket.

Thanks for listening and reading along! Don’t forget to support us on Patreon to get some extra content and access to our exclusive Discord. We also stream on Twitch and upload the highlights to Youtube.

The Podcast is produced by MJ.

Always a pleasure,

Ethan M. Wong

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


  1. Randy · August 15, 2021

    those old B/W Manong pics are great.


  2. Pingback: An Appreciation for Niche Vintage Menswear from the 1920s-1940s « Fashion
  3. JJ Katz · August 17, 2021

    Beautifully argued and documented. Good job.


  4. Wolf · August 18, 2021

    Another great selection of images and inspiration.


  5. peterhall1965 · August 18, 2021

    Have you seen Oldfield Outfitters in the uk? They nail this vibe.


  6. Pingback: Archiving My Clothes and Recontextualizing Them | a little bit of rest
  7. Pingback: Ethan’s Solo NYC 2021 Trip | a little bit of rest
  8. Pingback: Being Asian American and Into Menswear | a little bit of rest
  9. Pingback: The Purpose of Taste | a little bit of rest
  10. Pingback: On Irony & Subversion | a little bit of rest
  11. Pingback: My Senior Cords | a little bit of rest

Comment Away!

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s