The Vintage Sport Shirt


In the world of vintage casualwear, one article of clothing reigns supreme: the sportshirt. Because of its uniquely shaped collar (which lies flat and creates a notch, like a jacket’s lapel)  it is commonly known on the internet as the Cuban or camp collar shirt.  While the term loop collar has been thrown in the mix, it’s best known among true vintage enthusiasts and collectors as the sport shirt.

There have been a few articles written by other people on this subject, but none of have gone past the 1950s and 1960s in terms of history.  We’re here to put the record straight on this classic piece of vintage menswear that was worn by men of all ages in a variety of different outfits.


There is a perception that for most of the 20th century, when a man left the house he always wore a three piece suit, a crisp shirt, and a silk tie. While it is certainly true that the bar was set a bit higher than today, that does not mean that men never felt the need to loosen their tie. For a long time, in more relaxed situations men wore a soft, unstarched “negligee” shirt sans tie. Beginning in the 1930s, athleticwear found its way into the closets of non-athletes who were looking for a “Hollywood” look. While “sport shirt” originally referred to polo shirts and other such garments with a specific sporting use, the definition was broadened to include essentially all casualwear, including t-shirts and western style shirts.

The specific type of shirt we are discussing today remained wildly popular from the 1930s all the way until the 1960s, and by 1954 it was reported, that thanks to the shortened work day and post-war prosperity, production of sport shirts had surpassed that of work shirts.  We like to cite our sources.

And no, we haven’t found anything from the vintage era that refers to them as “cuban” or “camp collar” shirts.  Even Die, Workwear didn’t know what they were called and only referred to them as vacation shirts, even though they were worn year round. Based on conversations we’ve had with other vintage enthusiasts (who have scans and physical copies of menswear catalogs), there isn’t any mention of the type of shirt other than sport shirt, convertible collar, or loop collar.  The nicknames might be due to the fact that sportshirts wer extremely popular as casual wear (ie; to wear camping) during 1940s-1960s.  I defy you to find a classic midcentury picture of a family camping that does not have a sport shirt.  The “cuban collar” term probably points to its similarity in design to the guayabera shirt,  a cultural Cuban shirt.  Note that the guayabera lacks the loop fastening or any top button.

We firmly call them  sport shirts since it was the original term used.


We’ve talked about this type of shirt before.  It’s our go to for vintage casual looks simply due to it’s interesting design and the fact that it can go with anything! Here’s a few defining features that make it different than most shirts out there.

The Collar

The most distinctive feature of the vintage sport shirt is the collar. Referred to in advertisements as the convertible collar, its lack of collar stand piece allows it to lie flat on the wearer; it could still be buttoned up to accommodate a tie. However, much like regular dress shirts, the shape and length of the collar varied over the decades.

“Loop collar” shirt is what we initially called them, even though not all of the collars featured this closure.  Instead of a normal button closure, the top button fastened to a loop.  This was probably used to denote its casual nature and set it apart from regular dress shirts.  As time went on, this type of closure dominated almost all variants of sport shirts whether they were casual ones, for workwear, or Aloha shirts.  Generally, we call use the term “sport shirt” as an all encompassing term for a vintage casual shirt that features this collar.


The collar when fastened all the way up.

For use in and out of work!

1930s-40’s Collars

Early on, the shape of the collar was basically the same as a spearpoint- the only difference being the aforementioned lack of collar stand, and perhaps a slightly less dramatic curve. The mid 1930s saw the introduction of the loop collar, one of the defining characteristics of the sport shirt.  In general these collars were pretty wide and featured a teardrop variant of the spearpoint shape.


30’s sport shirt with regular button closure.


1930’s sportshirt.


1940’s loop collar with angular collar.

Wide 1940’s shirts.

1950’s-1960s Collars


Small and “sharp” 1950’s collar.

Shirt collars remained long until the mid 50s, when they shrunk to a point where they are comparable to what can  be found today. They also moved away from the “drooping spearpoint” shape and went for something more sharp and triangular.  In the late 1960s, the loop collar fell out of fashion, and simple button ups or button down collars became to go-to style shirt for all formality levels.


1950’s shirt with a short collar.


1950’s Japanese flecked wool shirt.


Trendy 1950’s shirt with extended loop closure.


Italian style 1950’s collar with no loop or top button.

1950’s “Italian” style shirt with loop fastening.

An example of a late ’60s sport shirt from A Serious Man, set in 1967.

The Pockets


Rounded flap pockets.

Most commonly (especially in the 1940s-1950s) these shirts featured two breast pockets, usually with flaps. But basically every variety that exists with dress shirts also existed with sport shirts- button down pockets, military style pleated pockets, single pocket, and even no pocket.  You’ll see every variation of chest pocket featured in this article!


Squared flap pockets on a 1940’s shirt.


Box pleated pockets.


Pockets sans flap.

Hem, Length, and Fit

As a versatile garment, these shirts could be worn either tucked in or untucked, and consequently were cut short (for high rise trousers) with a square hem.  The shoulders were yoked with “shirring” (also called gathering or micropleats) in order to provide a full look.

It’s important to note that these shirts weren’t  meant to be fitted.  They were either marked with regular generic sizes (S-M-L) or their “neck size”.  Like a normal shirt, they are supposed to fit the shoulders accurately, but they draped down in a loose, classic fit.  These shirts were comfy!


These shirts were made out of any casual fabric you could think of.  Flannel, wool, cotton, and seersucker were some examples, but the most common were gabardine (a soft twilled wool that drapes amazingly) and rayon (synthetic silk that is great for summer).  This is why the terms “vintage gab/rayon shirt” is pretty commonly heard among vintage collectors.

As time went on, they started using polyester in their shirts in order to mass produce them more easily.  This is apparent in the late 1950s and 1960s.  As you probably know, polyester is a fake fabric that traps heat; it’s best to avoid these.

1940’s shirts.

To emphasize their casual nature, these shirts could be found in a variety of plain colors and in crazy novelty prints.  The latter is mainly found among 1940s-1950s variants and can be heavily prized by collectors.  Personally, plain colors can be cool but prints are much more fun to wear with denim and tailoring!

How They Wore It

These shirts were really a versatile garment.  Guys wore these shirts almost any time they weren’t in a coat and tie!  Youth would wear them with cuffed selvedge denim and adults would wear them with their tailored trousers after work. You can see that the fit wasn’t always perfect, but that was okay.  It always looks slouchy and comfy while still maintaining the “cool vintage vibe”.

Here are some great true vintage  examples of guys wearing the vintage sportshirt in a variety of different outfits. We look at these all the time to get inspiration for our own looks!

Make sure to keep the collar length and shape in mind as you look at the pictures.  Remember that ones from the 1930s-1940s were wide and “droopy” (read flaccid) shaped while 1950s-1960s were shorter and more pointed.

Youth in the mid 1940’s.

Great look using a loop collar shirt and loafers circa 1940.

Slouchy 1940’s look.

1950’s casual style with a boldly printed shirt.

1930’s short sleeve variant worn with belt-less rousers and espadrilles.

Another 1930’s example

Plaid, pull over style shirt with pleated brown trousers and spectators.

Ad from 1941.

Bold check short sleeve with gurkha shorts. 

Wide 1940’s collars.

1940’s shirt patterns.

Lovely wide 1940’s collars.

Crazy 1940’s print.

1950’s style.

So much inspiration from this 1950’s guy. Note the smaller collar.

1950’s shirts with the Italian collar.

1940’s style with a wide runaway collar.

Cool downward angled loop collar.

Plaid sport shirt and selvedge denim.

Untucked style in the early 1950s.

Slouchy, just the way we like it.

Women can rock it too!

Sport Shirts Today

Unfortunately, the sport shirt today has lost a bit of its charm.  Firstly you have the ugly, “dad” versions of the shirt which usually made in a Hawiian motif a la Tommy Bahama.  The body is much too large and the designs are terrible; they’re also made from cheap cotton or polyester, so these are ones to avoid at all costs.

Modern designers have brought it back in some circles, but like suits before them, the design has changed a bit.  The long, floppy collars in the spearpoint-esque shape are long gone.  Instead, the collars have shrunk down to become even smaller (and more oddly shaped) than the already smaller iterations from the 1950s and 1960s.

Additionally, they have begun to be made in regular cotton (almost like a dress shirt) which I think loses its slouchy charm.  It’s not as airy as rayon and it doesn’t drape like a good gabardine.  However, the patterns tend to make up for it as designers seem to have maintained the use of cool stripes and prints.  They also haven’t brought back the large pockets that are a such characteristic of the vintage sportshirt, but that may be do remove any connotations to the “safari shirt” of the early 2000s. 

You’ll also see that a majority of these shirts are short sleeved.

The styling is pretty consistent to “tailored casual” as the styling is still paired with trousers and loafers.  It’s very similar to how I would wear it!

As we’ve moved into more modern and more casual looks, the contemporary iteration of the vintage sport shirt has started to be worn untucked (which is fine) with skinny jeans.  Most of the time, it’s worn by super skinny guys who buy a size larger, in order to make the shirt more flow-y and to contrast with their skinny jeans.  It’s almost like a pseudo Saint Laurent Paris style, where black chelseas or jodphur boots will complete the look.

I actually enjoy the look a lot, as it’s given me more ideas on how to wear my vintage sportshirts with more casual, contemporary items.  Not everything has to be tailored trousers and loafers, you know!

A great ensemble by Harry Styles wearing a TopMan version of the vintage sport shirt.

There are manufacturers today who still make sport shirts in the vintage way. I’m not talking about Tommy Bahama.  While most repro companies make Aloha shirts (which can be very pricey since no one makes good aloha shirts anymore), there are a few who make “regular” ones.  Southern California natives can also check out Sneaky Tiki Boutique in Long Beach (or their etsy), which similarly produces a line of reproduction sport shirts using extremely rare vintage fabric.  Their focus is primarily mid 40s to early 50s gab shirts. Because the fabric is in limited supply, usually there is only one or two sizes available per shirt.

A 1950’s style atomic print repro by Sneaky Tiki.

Groovin High (based in Japan) is another brand that creates beautifully patterned rayon sportshirts that feature chest pockets and wide collars.  Like Sneaky Tiki,  the Groovin High shirts are a little bold but that’s what makes them super cool!  Their site is a nightmare to deal with, but I have seen their products in some vintage stores where he price is pretty high due to import duties.

You can see the Groovin’ High shirts (and some others) in action on the Bryceland’s team in Tokyo.

Cuban collar shirt made by Ascot Chang.

Pajama shirt with the sport shirt collar, also made by Ascot Chang.

Sport shirt style wth trousers and Gurkhas.

While these shirts are great, I still think that they will never be able to replace true vintage ones.  Not only is it cool to have a piece of history, but some vintage sport shirts have crazy labels, details, and prints that you just can’t find anywhere else!

Ethan Newton in a vintage 1950’s rayon sport shirt and bespoke Ambrosi trousers.

Kenji Cheung in a dope sport shirt and cream trouser combo.  High Contrast anyone?

How You Can Wear Them

Obviously, we love love love vintage sport shirts.  They really do go with everything in your wardrobe! Like we’ve been stating, they’re a great source of personality to inject within your wardrobe.  If you go with a true vintage option, you’ll really stand out since not even the modern versions have the same collar, pockets, or feel as yours!  If you want to be vintage without committing to wide, pleated pants or wide lapeled suits, this is your way of doing it.


Short sleeve gab shirt with box pleat pockets, worn with work chinos.

Obviously the easiest thing to wear them with is jeans and boots, which is how youth wore them in the 1940s-1960s anyway.  It’s a classic look that is way more 1950’s than any 1950’s inspired look that the Americana camp tries to strive for.  You can always add a swap the cuffed jeans for some heavy chinos and add a leather jacket or gabardine short jacket to complete the look.

While plain sport shirts will look great with it, we prefer to add some color and pop by utilizing patterned sport shirts.  It’s a lot more interesting!


Short sleeve sportshirt with LVC 1878s.


Green gab sportshirt with well worn denim.


1950’s sportshirt with 1930’s leather jacket.



1940’s gab shirt worn with selvedge denim and loafers.



Awesome checked cotton sportshirt with western jacket and faded selvedge denim.


Rob in a vintage wool plaid sportshirt and military dungarees.


Sportshirt worn under a sweater and western 1950’s jacket.

Seersucker 1940’s sportshirt worn untucked with selvedge denim and white espadrilles.


Cream rayon, gurkhas, and espadrilles.

Shorts are also a great way to rock the look.  Gurkhas help push it firmly into the vintage category, but you can always wear any old flat-front, slim chino shorts!  They’re much better than wearing a polo  with shorts, since that is way too preppy.  The choice to tuck or untuck is up to you; we do both!


1940’s checked shirt with gurkha shorts.

Polo with loop collar, untucked with chino shorts.


Seersucker sportshirt with unstructured 1960’s suit.

Tailoring is also a great option.  Like the vintage guys of the 1930s-1950s, you can always opt to tuck in the sport shirt into some well tailored trousers.  In fact, that’s why the hem is so short; you’re meant to wear them with high rise trousers!  You can either rock them with the jacket (don’t forget the runaway collar) or with just the trousers.  This is my preferred method of wearing the vintage sport shirt, since I like to play the louche nature of the shirt with the clean lines of tailoring.


The look sans jacket.


Rayon sport shirt worn with linen jacket and wool trousers.


Pale yellow gab shirt worn untucked with blue linen trousers.


Casual tailoring.


The look sans jacket.


The yellow gab shirt worn tucked in.


Winter: 1940’s sportshirt worn under a crewneck sweater and flannel trousers.


White sportshirt worn with a brown DB jacket and chinos.


A fun sportshirt worn untucked with trousers (unseen).


Sportshirts worn untucked with vintage trousers.


Here’s a previously unreleased outfit that shows my (Ethan’s) preferred way or rocking gab shirts in a contemporary setting: using white or cream summer trousers.  It’s pretty close to the outfit on Kenji Cheung just without the use of high contrast and his dope, bold sportshirt.

It’s an easy going outfit that is easily repeatable with any color or patterned sportshirt; just add white or cream trousers! Boom, your look is grounded and ready for summer casual fun.  It’s not super vintage (it would be if you wore pleated trousers and spectators) but it has enough vintage personality to be a little different when compared to how most sartorial guys would dress for summer.  Like we said last time, high contrast is the way to go.



Another look with white linen trousers

Alternatively, here are some more modern casual outfits that take some inspiration from the SLP look.  The Hawaiian shirt above is worn with black skinny jeans and chelsea boots; it’s an outfit that’s probably familiar to Harry Styles.



A punk-inspired look with ivy vibes (white socks)


I also explored with using the shirt in a Japanese way that plays with fit and proportions. By combining the slouchy, full-bodied nature of the vintage sportshirt with the cropped, wide-legged Uniqlo U pants, it creates a different modern interpretation of the vintage look.  It contrasts extremely sharply with the slim-focused SLP outfits.  As you can see, these shirts are incredibly versatile that doesn’t always have to be used with vintage or vintage-inspired outfits!

Where to Get Them

You’ve probably gotten to this point in the article and thought to yourself “damn, these shirts are cool; where do I get them”?  Well luckily, these bad boys aren’t as rare as belt back suits or 1930’s buckleback jeans.  Almost every vintage store has them.  We’ve gotten ours through Reese’s Vintage Clothing, Paper Moon Vintage, Monsivais & Co, Roxy’s Vintage Deluxe, and Joyride Vintage.  These stores have almost every iteration of the vintage sportshirt, so it’s always worth checking out.  You can also find these shirts pretty easily on eBay. 

Prices (or suggested prices, rather) for true vintage  shirts can range from $20-$100+ depending on the fabric (composition and print), era, and condition. The most expensive ones are usually the 1940s-1950s ones with large collars and interesting prints/colors; you can expect the poly or poly-blend ones to be much cheaper.  Plain ones are the most common, which is what Spencer and I typically buy.

Obviously you can get modern versions by looking at ASOS, Topman, or H&M but they won’t have the same quality, fabric, and collar as true vintage ones. I’d recommend Groovin’ High if you want the rayon ones with large 1940’s collars and cool prints, but it may be hard to acquire if you’re not in Japan.


If you want a fun and easy way to inject some vintage style into your wardrobe, you gotta go with the vintage sportshirt. With its unique collar and great fabrics/prints, it’s sure to garner you some compliments!  Obviously the design has been updated today with a smaller collar and slim fit, but nothing compares to the real, vintage thing.

They really do go with everything, from tailored trousers to classic selvedge denim. If you need proof, just look at my articles from my Paris trip, since I wore them pretty much everyday.  Hell, you can even wear them with your sportcoat if you feel like rocking the runaway collar. We normally wear them with denim in order to keep things vintage casual, but if you do decide to wear it with tailoring, summer trousers (like khaki or cream/white) are the best bet in order to do a high contrast look.  However, feel free to experiment and wear them with skinny jeans or cropped wide leg pants! They’re such a great piece that can fit in almost any wardrobe.

We hope you learned something new, thanks to this article! Vintage sportshirts are a huge part of our wardrobe and I’m glad that we’ve finally been able to talk about it! I know that we’ve been writing a lot of long, educational pieces but I think it’s important that you guys have gotten some elaboration on some of the pieces we’ve been wearing since this blog was started.  Perhaps next time we’ll talk about belt-backs or go into detail about spearpoint collars! We’ve got a bunch of unique garments in our wardrobe that we just need to share with you guys.

Honestly, we like being able to talk about something that others (like Derek from Die, Workwear ) haven’t been able to get into.  Too many people refer to them as Cuban shirts, vacation shirts, or Aloha Shirts when that is simply inaccurate. These shirts were made of fabrics other than silk and rayon and weren’t just made for vacation.  Hopefully you’ve gotten a better understanding about these awesome pieces and that you’re able to try them for yourself!

Always a pleasure,

Ethan W. & Spencer O. 

Street x Sprezza 

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