If you’ve read my bio or any of my posts before, you know that it’s all about the 1920s for me!
As I looked into the enchanting realm of 1920s men’s fashion, I found myself transported back to an era that exuded unparalleled elegance and an unmistakable edge.
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No drooping pants, no underwear on display, no tennis shoes or flip flops, but tons of style and elegance.
The 1920s were a time of profound societal change, marked by both the extravagance of the Jazz Age epitomized by The Great Gatsby and the gritty allure of the Gangster Look.
In this article, I want to embark on a journey through the evolution of men’s dress shirts during this captivating decade. From the refinement of formalwear worn by dapper gentlemen at extravagant soirées to the bold and daring styles adopted by Prohibition-era gangsters, we’ll unravel the threads of fashion that defined an era.
Whether you are simply interested in the fashion of the times or looking for clothing ideas for your costume party, cosplay event, or upcoming wedding or other social event, you’ve come to the right place.
Join me as we explore the intricacies of 1920s dress shirts, uncovering the fine details, fabrics, and trends that graced the shoulders of men in this iconic period. Whether you’re a fashion enthusiast or simply curious about the 1920s, this journey into the stylish past is sure to captivate your imagination.
1920s Great Gatsby Dress Shirts
One thing about The Great Gatsby, despite being 100 years old, is that this book (and movies) never fails to entertain.
I’m sure Fitzgerald had no idea that we would still be drawing inspiration from his novel, but here we are!
Men’s clothing styles in Gatsby feature the dressed-up look. OK, let’s be honest, unless you were one of the working-class men, you wore a three-piece suit just about everywhere.
I love the Gatsby style because it remains popular with just a touch of nostalgia.
In this novel, the newly rich men like Jay Gatsby were well known for wearing not only the latest but also the most well-tailored fashion suit. Your pants should be a bit high waisted, but the legs should taper near the ankle.
Not skinny jeans tight, but they should get slimmer past the knee. No bell bottoms either!
In the novel, Gatsby wore a pink suit in the final scenes, and you can go for that if you like.
However, for summertime wear, you might like to try a white suit
with an awesomely colored dress shirt underneath.
When it comes to dress shirts, don’t be afraid to go with colors, patterns, and stripes. Colored shirts with white collars were extremely popular.
You can go for a shirt with an attached soft collar or one with a detachable stiff collar. The thing with detachable collars is that they come in a variety of styles. They can be removed and attached to long or short sleeve shirts and cross-match with other elements of the look you want to achieve.
When it comes to the “old money’ folks, like Tom Buchanan, you will want a suit that is conservative. No pink suits for Tom, just the usual herringbone,
or tweed suit in a dark color will do just fine.
Tom’s dress shirt should also be fairly plain. A solid color will do, as long as you have a matching tie and pocket square.
More on ties and other accessories a little later on.
Going to a Costume Party?
I’ve got you covered! If you’re going to a costume party this Halloween or another costume party during the year, you may not want to spend hundreds on a suit.
You can always go with the low-key gangster suit
or wear the full-blown gangster outfit that everyone will recognize.
Chances are that you have a jacket and pants in your closet. Even casual shirts will do with the right accessories, such as a hat, suspenders, a vest, and pocket watch. I like this accessory set because it literally has everything you need to pull off a terrific Gatsby costume for very little cash.
Check out this accessories set – I think the fake mustaches are really cute.
1920s Men’s Peaky Blinders Dress Shirts and More
If you’ve heard about this series but haven’t watched it, you are in for a real treat.
The outfits are similar to the Great Gatsby, with just a slight change of hats and a few other notable details.
Suddenly, everyone wants to dress like Thomas or Arthur Shelby. Or did you have more of a Michael Grey vibe on your mind?
The allure of the 1920s isn’t limited to the dazzling opulence of The Great Gatsby; it extends to the grittier, more rebellious aesthetics of the era, embodied in the notorious Peaky Blinders.
The show’s influence on men’s fashion is undeniable, and their dress shirts play a significant role in this evolution. Peaky Blinders men wear flat caps and form-fitting suit jackets, with their razor-sharp style that adopts a more rugged and practical approach to attire.
Their dress shirts often featured high, stiff collars and a distinct lack of flashy patterns, reflecting the utilitarian yet dapper look of the working-class streets of Birmingham.
These shirts, commonly worn with suspenders and waistcoats, exude a unique charm that captivates fashion enthusiasts to this day.
If you’ve got the suit and pants but lack the vest, you can easily pick up a fantastic-looking tweed vest and the dress shirt to go with it.
Are you an Arthur Shelby fan? Who isn’t? He’s so cute in a pathetic kind of way, but you have to admire his commitment to his brother, not to mention his impeccable suits!
Get this Peaky Blinders Costume!
Arthur Shelby was a fan of striped shirts, but nothing too loud. Go for the white collared shirt if you can, such as this one.
Why the white collar? Back in the day, men’s dress shirts had removable collars! This way, you could wash just the collar, making it sparkling white again, and put it back on the shirt.
Men didn’t always have money to own multiple shirts, as they do now, but I’m not sure anyone is interested in having to button on a collar!
By wearing a shirt with a white, rounded collar or penny collar (also sometimes called a Peter Pan collar) you can give the illusion of having an old-fashioned button-on collared shirt without the pain of having to put one on!
If you enjoy the rebel of the family, Michael, you’ll love this suit, complete with his awesome overcoat.
Get this Peaky Blinders Style Suit!
Michael Grey was quite stylish, but his fashion preference differed slightly from his uncles Thomas or Arthur. Note that his shirts are often plain white, but he wears dapper matching ties and pocket squares. More on those later.
Go All Out with Peaky Blinder-Inspired Hats and Their Timeless Appeal
We can debate about whether the real Peaky Blinders gang wore the newsboy caps, or if those flat caps came later on (in the 1930s), but when you wear this cap, everyone will recognize the time period.
Peaky Blinders hats were what are today called flat caps or newsboy caps. Not the smooth, one piece design we see today, oh no, Peaky Blinder hats were divided into sections because this is where they placed the razor blades.
You’ll see every Shelby man wearing this style of hat, except for Michael Grey. He wanted to set himself apart from the Shelbys, so he wore a Panama hat with a big wide ribbon, like this one.
I do favor those Panama hats, but in general, I wish hats would make a comeback. They added so much class and style to an outfit, don’t you think?
Get Your Swagger On! Gangster Shirts and Clothing in 1920s Fashion
The 1920s brought with it a sense of rebellion and bravado that resonated through the fashion of the era.
Gangster shirts and clothing, immortalized in the Prohibition era, epitomize this spirit of defiance and style. These garments, often seen on the likes of Al Capone and John Dillinger, captured the essence of the Roaring Twenties.
Gangster shirts and suits were characterized by bold pinstripes, wide cuffs, and a distinct lack of subtlety. Get the idea with pinstripe suits like this:
These men dressed with an audacious attitude that matched their law-defying activities.
I think that the gangster suit of the 1920s will never go out of style, not with the influence of films like “The Godfather” and “Scarface” keeping this style before the public.
The gangster aesthetic may have roots in a tumultuous past, but its undeniable charisma and sophistication ensure that it remains an enduring and influential facet of men’s fashion.
Go Plus-Sized Without a Problem!
If you’re loving these dress shirts, suits, and costumes but think that they don’t make them in larger sizes, guess again!
You can find nearly everything I’ve listed here in large sizes, including:
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Gatsby Dress Shirts
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Gatsby Suits
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Peaky Blinders Dress Shirt
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Peaky Blinders Suit
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Gangster Costumes
It’s the accessories that complete the look, so keep reading and we’ll talk about everything you need to accessorize your 1920s dress shirt and suit to pull off a truly authentic look!
Elegance and Class: Men’s Downton Abbey Dress Shirts and Suits Unveiled
One thing you can say about the men of Downton Abbey- they had class, but wow, what boring shirts!
Unlike the gangster shirts of Chicago or the striped men’s dress shirts that Peaky Blinders favors, take note of the shirts that nearly every man wears in this series. They are white. That’s it!
Oh, the suits vary, and they are incredibly awesome, but I can’t remember seeing any of the Crawleys or anyone else, for that matter, wear anything but a plain white shirt. Much like this 1920 dress shirt.
Not that there’s anything wrong with that but really? Plain white shirts? Well, perhaps they do this so that you will pay attention to their dapper suits.
There were a great many brown suits made from a herringbone pattern, I noticed, otherwise nearly all the suits are dark colored, such as dark grey, black, and darker shades of navy blue.
If you really want to go all out Downton Abbey, opt for the tuxedo. I think I’ve seen more tuxedos on Downton Abbey than in any other series or movie!
A three-piece suit (or a tux) with a white shirt, and you’re halfway towards the Downton Abbey look!
Finishing Touches: A Glimpse into Men’s 1920s Accessories
Unless they were very wealthy, many men in this era had only one or two suits and tuxedo for special occasions. This means that wearing the right accessories is vital!
1. Hats– Depending on the occasion, men wore a variety of hat styles.
For Gatsby, it was generally the Fedora
or the Panama hat.
These were good for work days. Businessmen wore them all around, and these hats were acceptable for everyday wear.
You can also go with the Straw hat, known as a boater, as a more casual alternative. You’ll see Tom and Nick wearing these in the movie The Great Gatsby.
For the working-man look or a Peaky Blinders costume, go with the Newsboy cap or flat cap.
2. Ties and Pocket Squares– Don’t be afraid to go all-out wild when choosing a tie, especially if you’re wearing a plain white or plain colored dress shirt.
Of course, you should avoid vulgar ties (pictures of naked women for example) and modern ties (ties with Homer Simpson), but you can pick bold colors and/or patterns and look vintage stylish.
Yes, if you are wearing the 3-piece suit, you need a tie and matching pocket square!
3. Shoes– don’t forget that shoes make the man, as they say. Don’t ruin an awesome Gatsby suit with tennis shoes! Invest in a nice pair of oxfords, and you can wear them for years!
Want to go with the gangster look? Try two-toned oxfords!
4. Suspenders– Belts were not used during the 1920s, so you can go with a pair of spiffy little suspenders, and you’ll be feeling like you are living in Jazz Age!
Check the pants on your chosen suit. Most pants in the 1920s had buttons for suspenders, but if your more modern pants don’t have buttons, use the type of suspenders with clips.
There are other accessories you might want to add to complete your vintage look, including walking sticks, cuff links, overcoats, and a tie pin, but these are a matter of taste.
A Few Words about 1920s Watches
As you might imagine, I get invited to quite a few costume parties and cosplay events , even weddings with a Great Gatsby theme.
One thing I’ve noticed is that the best dressed, most fantastic-looking men tend to wear everything mentioned above, including a pocket watch and chain.
I can’t help but notice when that pocket watch is missing! It’s such a time-stopper (pardon the pun) that you can’t help but feel as if something is missing when you don’t see the chain draped across the vest.
You might think that a pocket watch is a big expense. If it was real gold or silver, then yes, it would be, but what if I told you that you can wear an awesome pocket watch and chain for less than $20? Check this out!
Wearing a popular suit jacket from previous decades and a popular hat or shoes in a popular style all help with the overall appearance of your Gatsby look. That’s all true, but adding something as simple as a pocket watch and chain will move you from the “nice suit” category to the “WHERE DID YOU GET THAT OUTFIT?!” category.
You can skip the attached collars and collar pins, or you can wear the exact Peaky Blinders shirts that the characters do. You can wear bow ties, single barrel cuffs, and those wide brim hats, but minus that pocket watch- it’s like a cat minus it’s tail.
A Few Tips Before You Go on 1920s Men’s Fashion
As I conclude this journey through the captivating world of 1920s men’s dress shirts and clothing trends, I can’t help but marvel at the enduring style and influence of that remarkable era.
The Roaring Twenties brought about a fashion revolution that pushed boundaries and redefined what it meant to be a modern man.
My top tip for dressing like a dapper gentleman? Wear sharply tailored, three-piece suits with the right type of hat, tie, shoes, and a pocket watch.
That said, let’s not forget that the 1920s were also a time of cultural dynamism, where rebellion and innovation were celebrated. As we look back, we should be inspired to infuse a touch of that audacious spirit into our own styles today.
So, my fellow fashion enthusiasts, I encourage you to explore the rich history of men’s fashion and draw inspiration from the 1920s.
Consider incorporating a vintage twist into your modern wardrobe, whether it’s a classic fedora, a sleek waistcoat, or simply a well-crafted dress shirt with a detachable collar. Embrace the elegance and creativity of the past, and make it your own!
In doing so, we honor the legacy of the 1920s and keep its fashion flame alive. Here’s to timeless style and the courage to be bold in our sartorial choices.
The 1920s await your fashion revival – are you ready to embrace it?
