Honestly, I can’t find much info on this style of shirt, known as the vintage pull-over or gaucho. In terms of design it’s basically similar to a polo shirt, just with the collar of a vintage sport shirt. Some featured regular buttons while others featured loop buttons throughout; placket length also differed among models. Lastly, most were long sleeved and had ribbing on the bottom hem and sleeves.
Basically, it was a novelty shirt popular among youth and young adults during the 1940s-1950s. With crazy prints, wide two-tone collars, and patterned bodies, they really were the “cool trendy thing” for boys to wear. Some gauchos were plain (named so for their crazy buttoning) while most went crazy with designs. Others even had a “dickie-style” fake collar thing, where it would mimic the look of an undershirt. There’s probably a plethora of evidence that the 1960s took inspiration from this style.
It’s important to note that “gaucho” isn’t a real term; it was just a branding thing, like how Kleenix has come to define “facial tissues”. They were named as either pull-overs or sport shirts in menswear advertisements. However, pullovers also came to mean sweaters and sportshirts became the name for the popular casual shirt style from the 1930s-1960s. In order to differentiate these cool shirts from the others, we decided to call them gauchos. Obviously design and colors for gauchos varied from brand to brand, but it’s a good catch-all term for any unique vintage pull over shirt.
Because of their crazy nature, this shirt is prized among rockabilly and hardcore vintage collectors. Unlike regular sport shirts, these bad boys are incredibly rare. If you find them on eBay, they sell for $150+! Whenever I come across them, they’re either super big (which is highly prized) or a child’s size. Most guys flip them if they thrift or flea-market them, since a lot of money can be had. If you find one, bring it to Viva Las Vegas (the biggest rockabilly convention) and sell it!
Here you’ll see a variety of different gaucho shirts. You can probably see that it was definitely meant for casual wear, paired with trousers or shorts. I couldn’t find much of it worn with true tailoring (sport coat), but it was probably best done with plain gauchos. It’s honestly a really weird shirt that no one really knows about! I’d liken it to the print polos that were popular in the past 3 years.
Aren’t they great? These shirts are filled with so much more personality than a vintage sport shirt thanks to their crazy design. I’ll admit, it’s a bit hard to wear them apart from a vintage outfit (you’ll be the envy of the vintage community by far), but it’s a cool look.
Because it’s pretty hard to obtain (or just too expensive), it’s difficult for me to write accurately about it. Luckily, we got our hands on a few and decided to put together a couple of outfits to show you how you can wear it!
Long sleeve, Checked Gaucho
This is a cool gaucho that I picked up from the Rose Bowl Flea market for $70. The seller actually wanted $100 but I was able to haggle him down! By feel (since there isn’t a label inside), it’s made up of a slightly heavy (yet soft) cotton. It stretches at the bottom, but not much at the chest or head, which makes it a bit hard to put on. However, it’s extremely comfortable and is perfect for a cooler summer day.
You can see it’s got a vibrant checked design, wide collar (which makes this very 1940’s) and a flapped hidden pocket. I’m honestly not a huge fan of the faux-undershirt dickie-like thing it’s got going on; it’s distracting and just not a good look if I want to be taken seriously. However, I don’t want to ruin the shirt and I want to preserve it in its natural condition if I ever feel like reselling or passing it on.
Styling wise, it was a bit harder than I thought, due to the bold checked pattern and the faux-undershirt. I knew that pairing it with pleated brown trousers (from my Vulture Suit would work, but I was at a loss with the jacket. I decided to wear it with my white belt back jacket for high contrast, but I think it looks best with just the brown trousers.
Isn’t that a lot more easy going and natural? Most of the time, I advocate wearing a jacket with louder shirts in order to tone it down, but there’s nothing wrong with letting it shine. It ends up looking like a regular long sleeve polo outfit, just with some rare (or odd), vintage detailing. Plus without the jacket, it’s pretty much how guys back in the day would’ve worn it: with casual, pleated trousers. Not sure if the 1940’s gents would’ve approved of the sockless penny loafers though.
The Polo Style Gaucho
This next gaucho is actually more of a summer, polo style one that I bought from the Barrio Dandy. It’s got a dope flecky and block-striped rayon fabric that has a ribbed hem and short sleeves, making it perfect as a summer pullover. The collar is just like a sport shirt collar, with a loop fastener. This gaucho is less stretchy than the previous shirt and was a bit of a pain to put on and take off, even though it fits perfectly. Sweaty skin with rayon is no joke and it tends to catch on the fabric, making it extremely difficult to take off without damaging it. Maybe I need some sort of fabric grease to disrobe!
Like always, I always try to make things work with tailoring. I wore a brown wool jacket (with runaway collar!) and blue trousers from the 1960’s unstructured summer suit. If you know me, you know that I love pairing blue and brown together, so this was a natural combo for me! I added a panama for good measure. Looks like a summer advertisement from 1941: slightly slouchy but completely comfortable.
Even though putting all the cool pieces together makes me feel all “vintage-y” inside, nothing beats the simple combo of the gaucho and trousers (with sockless tassel loafers). It’s less costume-like for sure and much more versatile if you want to wear it apart from a vintage event.
This shirt just might be my new favorite casual piece by far. The subtle block stripe and collar are fantastic, which are both things that no one does anymore. If uniqlo made these along with their spread collar shirts, I’d grab a bunch. It’s the least “gaucho” out of all the other shirts, but that what makes this particular shirt extremely versatile.
Blake also had a polo style gaucho (defined by the placket and collar) that comes to us in a gorgeous saturated green gabardine. Unlike my striped one, his is longsleeved, which he simply rolled up for comfort in the hot sun. I definitely like the ribbing on these gauchos, since they make the shirt more interesting than a regular pull over or polo and because they add waist suppression.
He toned down his green gaucho with some grey herringbone slacks and white bucks. I think loafers would’ve looked way smart, but white bucks are the underused casual shoe of classic menswear.
Now this is what a gaucho shirt is: Long sleeves (which I rolled up, ribbed hem, loop collar, and a two-tone color scheme with a checked body. The shirt is made from a wool gabardine (I think) with a rayon body; like the previous shirt, it’s not as stretchy as I had hoped. Overall, this gaucho is so perfectly rockabilly and a great statement piece; I especially love how this one does not have the faux-undershirt, which makes it a bit easier to wear. The smaller collar makes this probably a late 40s-1950s piece, which makes sense since this is pretty bold compared to the previous ones I posted.
The story on how I got this one is a little weird. My friend took a trip to Idaho and in Boise, she went to a random vintage shop and snapped me a picture of this shirt! It was marked a size “S” and I immediately told her to buy it if the price was right and ship it to me; I’d pay her back immediately. Unfortunately, she left but she told me the name of the store. I looked it up and called in to talk to the owner. The owner was super nice and measured it out for me and told me the price: $32 with $6 shipping. A rare gaucho for less than $40? Hell yes.
To style the shirt, I decided to go the same route as I did with the vintage sportshirts: I wore it with white summer trousers. The use of white/cream linen or cotton trousers is extremely useful, especially when you’re wearing a bold vintage shirt. You can recall that Mr. Kenji Cheung of Bryceland’s did the same thing with this patterned sport shirt. I think it works well here, which contrasts with the blue of the shirt. I honestly can’t think of any other thing tailoring wise that would work with it other than these trousers or perhaps a brown one; khaki would make it look a little boring, in my opinion. I wouldn’t recommend wearing a sportcoat with this (a blue one would work) since the shirt is bold and you’d probably want to show it off!
Can I go to Pitti now?
Blake decided to join in on the fun with this gaucho shirt, which is simply bonkers. His is made of rayon, with a short 1950’s collar (rounded edges? woah!) and a chest pocket. But that’s not the crazy part. In the placket, he has three loop buttons that are extremely close together. I’m pretty sure they are always supposed to be fastened, but these are purely for decoration. It honestly gives me some nautical vibes.
Like most of the outfits here, he pairs his guacho with a simple pair of pleated blue trousers. I’m glad we were able to include Blake in this, since he shows us a completely vintage outfit that isn’t too crazy! It probably helps that everything fits him impeccably.
If you’re wondering how Blake got this rare shirt for cheap, it’s because he’s super skinny. This is probably a literal youth size and not many guys today can fit into it. Most of the time, these rare stuff sit forever on shelves since most vintage enthusiasts (or even just gaucho, rockabilly guys) are way too large to buy them. Blake is very lucky (or cursed).
The Aviator Zip Shirt
The last piece we’re going to see is this amazingly rare asymmetrical zip pull over that Blake happened to find in a thrift store; they normally go for over $100 due to their weird fastening. Its also called the aviator zip, due its similarity to aviator jackets back in the 1930s and 1940s. That’s why they’re so rare.
With its cool flapped chest pocket and cool “convertable collar” (alluding to its sport shirt nature) , it’s a great piece to wear as a statement piece. The fact that it’s made of a light brown/grey gabardine makes it easier to pair with dark pieces like navy trousers; Blake decided to don his grey herringbone slacks yet again.
With Denim and Sneakers
Something that I stress almost all the time is to try and find clothes that are versatile. These gaucho shirts are no exception; if you wear them like the sportshirts we talked about in the last article then you can definitely get more wear out of them! Putting the gauchos with tailoring are a great way to spice up your sartorial wardrobe, but they can go just fine with casual pieces.
Obviously denim and boots is a no-brainer (it’s how guys in the day would have probably worn them) but lately I’ve been exploring how they work with sneakers. It’s a pretty young look, but after seeing this guy rock a similar outfit, I knew I had to try it for myself.
Here’s the bold two-tone Gaucho worn with my trusty 501CT selvedge jeans and thrifted 70’s Converse. As you can see, it’s clearly a youth outfit, but I think it works well enough for what it is. I’ll probably stick to more tailored pieces (like swap the shoes for loafers), since this projects an image that’s a bit too young for my taste. I ain’t no kid!
Here’s an outfit that is directly taken from the inspiration. The bottom half is exactly the same as the top (501CT and vintage Converse) but the overall look is more mature and even more work-wear inspired. It’s probably due to the fact that the gaucho (the striped, polo style one) is the most versatile out of the bunch and is in a great subdued, summer color! This has to be one of my favorite casual outfits ever. I’ll probably repeat it with tucked in t-shirts and other polos!
Gaucho shirts and other novely pullovers from the 1940s-1950s are great vintage garments that are filled with crazy details. Whether its a two-tone body, contrast collar, heavy ribbing on the hem and sleeves, or just odd buttoning, you’re sure to stand out if you get your hands on it. The only problem is that these shirts are incredibly rare to find; if you do find one, they tend to be expensive!
However, don’t pass one up if you find one! You can probably flip it on eBay if you do it right or you can wear it! I always recommend white trousers if you need to pair it with modern tailoring, but you can’t go wrong with selvedge denim and a pair of white sneakers. It’s a look that I’ve been trying to do, since you can’t always be sartorial!
I hope you guys learned a bit more about the bolder cousin of the vintage sport shirt. If you look hard enough, you might get lucky and get your hands on a cool guacho! You’ll certainly be the envy of vintage collectors.
Always a pleasure,
Street x Sprezza
Photography by Spencer O. and Mila P.