Vintage Casual ft. Joyride: Vintage For Men


I know that we focus on tailoring a lot on this blog, but I think its time that we explore the seldom seen side of Golden Era Style:  casual.

While its true that most people in the 1930s-1950s would dress up (seldom seen without a tie or sportcoat), casual style definitely still existed.  It was a bit more tailored in the 1930s to the early 1940s, but after the war, more guys would wear jeans and sportshirts (a button up casual shirt that usually had camp or loop collar).  The resulting style would go on to influence a bit of ivy in the 1950s and 1960s as well as be the defining factor in Americana/workwear outfits of the 2010s; you might as well call “vintage casual” proto-workwear.

Like today, young people in high school and college were at the forefront of this “latest trend” of American 1940s-1950’s style, perhaps pushing us to the casual nation we are today.  Here are some of the pictures that Spencer supplied that really exude what “vintage casual” is all about.

James Dean with wool pants, button up shirt, and leather jacket.

School style featuring varsity jackets worn with chinos and wool pants!

Cuffed jeans were worn with derbies and boots.  Note the tucked in sport shirts and tee shirts!

Probably my most favorite look, showing you that white socks and loafers weren’t always ivy. 

Getting the the theme of short jackets, sport shirts, and trousers yet?

Plaid sport shirts, tees, and both trousers and jeans!

As you can see, “vintage casual” is pretty simple compared to the amount of pattern mixing thats involved with its sartorial counterpart.  For tops its usually a simple tee shirt, a sport shirt, or a plaid sport shirt; bonus points for having a loop (or camp) collar.  For pants, you can still wear trousers but chinos or cuffed denim are excellent choices.  Lastly, layering with a cool vintage jacket is a must for colder seasons.  Denim jackets, chore/work jackets, leather jackets, and varsity jackets are all great to put over your ensemble.  The specific choice depends on which specific look you want to do, but most vintage casual stems from either workwear, school/collegiate style, or sportswear.

Plus you’ll note that loop collar shirts are the main style worn in these “vintage casual fits” but they’re hard to find today.  They’re a vintage detail that truly make a look 1940s-1950s. Today, casual shirts exist, but they mostly have the same point, semi-spread, or button down collar style that regular dress shirts have.  This means that whenever someone wears a loop collar, it definitely looks straight vintage.  Luckily they’re stilll very common and a cool piece to add to your wardrobe if you want to slowly get yourself into a vintage/vintage inspired style.

So for watching White Christmas this past week, the guys and I went vintage casual.  Again, its very similar to Americana/workwear but its the subtle vintage details that keep it different, mainly through the use of true vintage shirts and jackets instead of something modern from Rag & Bone or Carhartt. It’s also my pleasure to feature the men from Joyride: Vintage for Men, a fantastic vintage menswear store that not only has true vintage suits but an impressive collection of casual items and accessories!  We’ve seen them before in our Inspiration LA post a long time ago. They’re in the Orange Circle, so if you’re local you should check them out.  It’s a perfect store for those of you who like these types out non-sartorial vintage outfits.



My outfit takes inspiration from 1950’s high school/collegiate style, with a simple combination of sportshirt, sweater, flannels, and varisty jacket.  I’ll say right off the bat that the only two true vintage pieces are the sportshirt and the varsity jacket.  However, with the right styling and details, it can look straight out of 1950!   Its still semi-tailored, but as we saw in the inspiration pictures, wool trousers were still worn as casual pieces.   The fact that mine are high rise and pleated (but slimmed down) still make the look “vintage casual”.  Might be more dressed up than what people consider to be casual today though!

Keen eyed fans of my blog will notice that this jacket is the same one that I purchased while on my SF trip and the one I wore when I first got my selvedge denim!


Its winter here in California, so layers are a must.  The pants are flannel, the jacket is wool (with a quilted interior), and the sweater is wool/cashmere, so I’m staying warm!  Note that like the vest in my posts about the ivy suit and the 1930’s Christmas party, this vintage varsity jacket ends at the true waist where the trousers end.  Might be weird for modern pants and jeans (that sit on the hips) but perfect for high rise trousers!

Without the varsity jacket, it looks a bit more modern but again, the details like the high rise, the pleats, and the camp collar give this a more “college student in the 1950’s” vibe.  While other looks of the vintage era can set people off due to lapel size or tie prints, I think that vintage casual is a great half-way point for people who want to have the vintage vibes but don’t want to go into tailoring or formal wear. You might even say that vintage casual (in regards to my outfit) is pretty good combination of tailoring and casual wear; its Street & Sprezza 😉

1960’s Varsity Jacket, 1940’s loop collar shirt, Blue crew neck sweater from BR, Flannel pleated trousers from Polo Ralph Lauren (thrifted)



Spencer’s outfit goes a bit more workwear, but its still a casual outfit that would definitely be seen on a high school kid in the 1950’s.  Compared to mine he’s dressed down, swapping flannel trousers and bluchers for selvedge denim and boots.  It might be the closest that we can get to the current trend of Americana/workwear, but again, its the details that set it apart.  Still, its a great outfit and perfect for a California winter.


This is what I mean by details.  Instead of the typical denim jacket or chore coat, Spencer has a 1950’s short jacket with western styling.  Like my varsity jacket, it is meant to end at the waist.  The western styling comes in not only with the sherpa lining but thanks to the sherpa trim on the front yolk.  It’s definitely a statement piece that works well with the rugged look of jeans and boots. A jacket like this is not something that you normally see spread out on an #aesthetics menswear IG page.  Plus Spence only paid $15  for it on eBay.  Not a bad price for something that’s almost 70 years old!

What I like about Spencer’s outfit isn’t just the jacket, but the use of the sport shirt and sweater combo.  Note that in the inspiration pictures, guys were still pretty “presentable” with their styles.  They had tucked in shirts and combined their sportshirts with sweaters. Again, this styling makes Spencer’s outfit more “vintage school casual” instead of the rugged, modern Americana interpretation we see today!  I love when people put different spins on stuff, especially when they look to the Golden Era for inspiration.

1940’s sportshirt, Luther Denim 47′ jeans, 1950’s western style shortjacket, Sweater from Uniqlo, Chippewa 1930-1940’s repro boots.  



Blake is probably the odd man out in the group, since he goes for something a bit more formal.  Instead of something inherently casual or something from the 1950s, he’s pretty 1940’s, wearing an epic green spearpoint collar shirt with high rise wool herrinbone slacks, and a 1950’s gaberdine ricky jacket.  A sportshirt with a loop collar would have made his outfit a bit younger or a bit more casual, but Blake looks great nonetheless!  He looks like he’s a young man from the early 1940’s, just sans tie.  Again, note the “short length” of the jacket; it ends at the waist!

Overall, it’s a great look.  Most guys in the Golden Era would sport this when going out.  They would simply ditch their sportcoat (and tie) and pop on their gab jacket for a “casual outfit”.


Check out that lining!  Modern casual jackets don’t have that!


Just want to take this small moment to say that pleats are still awesome and drop loop trousers are freaking cool.  They’re just some of the details that make a vintage look!

1950’s gab jacket, 1930’s spearpoint shirt, 1940’s wool herringbone pleated trousers,

1980’s suede bucks, 1930’s fedora



Eli (@tobacco_road_artnvintage) has one of the most impressive collections of vintage menswear  I’ve ever seen.  He has belt back suits, suits from the 1910s, sportshirts, fedoras, and fantastic leather jackets.  He’s one of the workers at Joyride, and he can usually be seen in something “vintage casual” or workwear; the outfit that I photographed is no exception.

He keeps the tucked in sportshirt that we’ve all been doing, but he adds a kickass vintage leather jacket and modern japanese selvedge denim to the mix.  Sure, it may not be complete vintage or something straight from a 1940s photograph, but the detailing and styling is all personal.  No one said you had to be an accurate representation of an era! And to be quite honest, Eli probably has the best outfit of anyone here.  Its a mix of workwear (with the selvedge denim and cuff) with some definite vintage vibes, thanks to the 30’s leather jacket, sportshirt, and cap.


Let’s talk about Eli’s jacket.  Now McCoy’s may make some of the best leather jackets today, nothing beats the detailing, quality, and history of a vintage leather jacket.  This one is from the 1930’s and is practically a holy grail.  Cut from horsehide, it has a button cuffs, side tab a adjusters, two curved flap pocket (western detailing again), and a back yolk with a pleated belt back.  Just freakin amazing.  The jacket may not be new, but I think leather looks even better with age.


Baby got back.


Pocket detailing.


Other than high end brands like Schlott or McCoy’s, you just don’t get cool labels like that.


Can’t be vintage casual without a deep cuff on your japanese selvedge denim!

1950’s western sportshirt, 1930’s leather jacket, vintage Japanese redline selvedge Lee jeans, 

vintage Chippewa boots, tweed panel cap 



Rob is the man.  He’s been collecting for years, crafting a fantastic personal collection of both suiting and casual wear; in fact, he’s the owner of Joyride: Vintage for Men.  What’s amazing about Joyride isn’t the impressive collection of vintage clothing  and accessories from 1910s-1990s but the wealth of information that Rob (and Eli) have.  His store has become sort of a meeting place for vintage ethusiasts, denimheads, workwear guys, and even casual fashion ethusaists alike, sharing their latest finds and showing off their coolest pieces.  Rob is an extremely nice man and I’ve learned a lot from going to his store. It’s pleasure to finally add him to the annals of Street x Sprezza!


His outfit isn’t flashy like the rest of ours, but there’s something great about subtle outfits.  At first glance, it may look like he’s wearing a regular plaid flannel shirt, but notice the details! It’s higher cut (meant to be worn with high rise trousers or jeans), it has two breast pockets with flaps, and features a very prominent collar.  Just compare it to the ones you see at J. Crew.  Rob’s 50’s Pendleton shirt has a very interesting camp (or loop) collar that actually points forward.  You definitely don’t see that kind of thing anymore, which makes his outfit decidedly more vintage than just a normal guy wearing a plaid flannel.

Take a good look at his jeans.  They’re obviously high rise, but the pocket detailing is what matters.  The patch work looks like the pocket treatment on army trousers, which is exactly the point: the jeans are 1938 US Army dungarees.  Amazing, right?  You can either go vintage for this stuff, or pay a lot more for reproduction.

WWII Roughcut boots, 1950’s Pendelton flannel, 1938 Army dungarees, 8 Panel cap


As you can see, going vintage isn’t always about wearing a suit and tie.  There are definite ways to go with some vintage vibes even when you’re dressing down.  Honestly, vintage casual is probably the easiest way to obtain vintage clothes.  Besides leather jackets and the occasional short jacket, vintage loop collar shirts are pretty readily available on ebay, etsy, and most vintage stores.  The small detail of having that style of collar really sets your outfit apart, especially since this type of look is very similar  to the current trends of Americana/workwear.

Looking at old pictures of young people in their casual clothes, you have some options when it comes to trousers and footwear.  You could go with high rise trousers or (even better) wear some high rise selvedge denim.  For the latter you can either try to find true vintage or get some from Levis or another reproduction brand.  Japanese companies also make some of the best denim in the world.   Add a double or deep cuff, you’ve got yourself a great garment that can be worn in a variety of outfits.  Then, finish off your look with a cool short jacket! You can go with a wool varsity jacket, a gab short jacket, or a statement piece and you’ll definitely have that vintage casual look down!

I hope you enjoyed this latest article and I hope it gives you some inspiration for your style. You can definitely still be vintage even without a suit!  Big thanks to Joyride: Vintage for Men for letting me shoot in their store and for being apart of this article! If you haven’t been there, I highly recommend it as it is an amazing place to visit. There are racks of organized shirts, suits, and pants from every era, including ones from today that could work in a vintage outfit! In addition to that, they have military jackets (where I got my Field Jacket), hats (as well as a hat workshop where they can stretch, clean, and reblock your hats), vintage ties, a a butt-load of accessories!   I highly recommend them.

Always a pleasure,

Ethan W.

Street x Sprezza

Photography by Ethan W. and Spencer O. 


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  18. alexandro madher · December 4, 2020

    hi , do you have any info for the Spencer short jacket like model or trade mark?
    do you know a similar model like this, modern manufacturingor whatevers regardless of color?

    sorry for my english 🙂


    • Ethan M. Wong · December 9, 2020

      Hi Alexandro! Unfortunately there is no label, but definitely try to look up 1940s-1950s hunting jackets, preferably in canvas. J. Crew barn coats are similar, but the L.L Bean ones are also good! Happy hunting!


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