Dress Like A 1920s Gangster: Clothes of Boardwalk Empire


Boardwalk Empire: Men's Fashion

Aside from being an all around absorbing viewing experience full of gangsters, dames, and all kinds of 1920s goodness, HBO's Boardwalk Empire showcases just how stylish of an era those gay old days were. And here we're going to get down to the nitty-gritty of just what makes the men's style of that time just so swell and dandy.

Dressing in an authentic men's 1920s getup isn't as easy as it seems. There's more to it than just fedoras and three piece suits, you know? Accessorizing is king if you really want to look sharp, and there are different degrees of what kind of look you can go for. You can be a highfalutin' gangster like Nucky, with his flamboyant accessories and colorful attire, a common street hood with newsboy caps and bowler hats, or you can dress to the nines with bow ties, top hats, pocket squares, and boutonnieres.

Whatever suits your needs, we'll try to at least give you a good layout of the essentials of swanky 20s dress by using the memorable characters of Boardwalk Empire as our primary examples of what to wear if you don't want to dress like just half a gangster.

The Three Piece Suit

First things first. The one absolute must-have for every 1920s, prohibition-era style men's fashion is the obvious three piece suit. So before reading any further into this list, go ahead and go out and get yourself a swell-lookin' suit jacket, vest (waistcoat) and pair of trousers (and, for the love of god, make sure they all match). Then throw those pieces in with a swanky dress shirt and a tie of your choosing. While either a plain, solid colored suit or pinstripes will both do just find (both are appropriate for the time period), there’s just something about those pinstripes that just screams that you’re a Tommy gun-wielding gangster from the nineteen-twenties. But, hey, it’s your choice.

In Boardwalk Empire literally every male character can be seen wearing a three piece suit at one time or another. If you’re a man, this will be the very foundation of your attire. However, not all three piece suits are created equally. For instance, if you’re going for a wealthy, no-class gangster, you’ll want plenty of bright, garish colors and those pinstripes I mentioned earlier (these are for the street guys who have stumbled into wealth, without ever having learned what tastefulness is). For sheer class, you’ll want to take your cues from Arnold Rothstein’s wardrobe, which is more elegant without ever being overly showy. For a plain old street hood, keep things simple with solid colors — browns and blacks — and very little of the accessories that I’ll be mentioning later on, further down this list.

If you're on budget or simply shooting for the bare minimum, this is all you'll need. Alone, it’ll look great for the 20’s, 30’s, 40’s, 50’s, 60’s (think Roger from Mad Men) or literally any other decade. That’s because the three piece suit is timeless — it never goes out of style.

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The Hats: A Swell Hat Can Be Your Defining Accessory

A man’s hat in the 1920s could speak volumes about who they were as a person. They were all about class standing and what to wear for what occasion. So before you go out and purchase any old headwear that catches your eye, it's best to know ahead of time where you'll be wearing it and what kind of image you’ll want to be presenting. The easiest and safest choice of hats for most people and occasions is the classic fedora. It can be worn almost anywhere, by anyone, and should go just fine with any suit that you chose to sport with it (make sure to go for matching colors).

If you want to go with a more high-class look, try going with a top hat or perhaps a Hamburg; the former if you’re wearing a suit with tails, the latter if you’re simply a wealthy bastard. On the other side of that coin, if you're just a poor kid starting out on the streets, or a regular working-class Joe, the bowler hat, flatcap, or newsboy hat will do just fine (the latter is what we see Jimmy wearing during the early episodes of Boardwalk Empire, before he begins moving up in the world, and what we see Richard Harrow wearing throughout almost the entirety of the series).

However, options of headwear don’t end there. If you plan on having a party outdoors in warmer weather, or kicking back at the beach, or even lounging around on your yacht, a straw boater hat is good for both upper and middle class fellas. It’s inexpensive, comfortable, casual, cool (both literally and figuratively), and looks great. However, if you go with the boater hat, be aware that this isn’t a headwear for regular, everyday streetwear and criminal activity, and would best be worn with light colors.

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The Suspenders - Banks aren't the only thing gangsters need to hold up...

While belts had gained some popularity during the 1920s (and will work just fine with your suit, if that's all you have), it’s suspenders that are the real-deal when it comes to holding your pants up if you really want to be a good looking, true-blue, time-appropriate gangster who wants to keep from dropping trow. Aside from their obvious practical purposes, suspenders also happen to look a million times better than belts (when you’re wearing them with a nice suit, at least). This was just as true in the days of prohibition as it is today.

If you have your doubts about how fashionable a pair of nifty these garments are, that’s probably only due to a series of terrible fashion trends that began sometime in the 1980s — not to mention everyone’s favorite sitcom nerd, Steve Urkel — which caused suspenders to grow an unfortunately bad reputation over the years. But that bad rep merely stemmed from the suspenders being worn in inappropriate ways by people who usually weren’t even wearing them with suits.

In earlier years, suspenders were considered an undergarment, it must be remembered. They were meant to be worn under both your jacket and your vest (but not your shirt). So when we see someone wear suspenders with a t-shirt and a pair of jeans, 1980s style, it’s not exactly what the clothing was designed for and is likely to look… well, awful.

When worn correctly, however (that means with a suit), you’ll look and feel great in your suspenders; even if no one can get more than a passing glimpse of them throughout most of the day. And when the day is done and you’ve shed your jacket and waistcoat, and rolled up your sleeves, you’ll look like a real tough guy when you’re wearing your suspenders in only your pants and dress shirt.

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The Collar Pin - Give your collar an added pop

Here’s something you may not be familiar with but should probably learn about immediately if you want to dress like a real, 1920s gangster. It’s called a “collar pin” (also known as a “collar bar”), and it’s so ubiquitous to clothing in that era than you can see it being worn by virtually every male character all throughout the series of Boardwalk Empire.

Not to be confused with a tie clip, a collar pin is a small, metal accessory that’s designed to hold the two ends of your dress shirt's collar together. It passes under the knot of your tie, lifting it slightly to give it a nice looking appearance of an arch, as it keeps your collar securely in place. While the pin is small, mostly hidden, and subtle in its appearance, it’s nevertheless a very visually pleasing addition to your outfit.

These collar pins, though, weren’t designed to be merely a pointless and shallow part of your wardrobe, used only for enhancing your style. In the 1920s, collars were made to be soft for comfort and therefore could be easily wrinkled. The collar pin was the practical solution to this problem, as it kept the collars neatly in place and wrinkle free. Today, shirts are made differently and the collar pin isn’t quite as needed as it used to be. But it’s still a visually appealing little “splash of class” for your outfit. And, if you’re really shooting for full authenticity in your 1920s wardrobe, it’s an absolutely essential addition; as we can see from the series, where a collar pin is worn by nearly every man in sight.

Both vintage and new collar bars and pins are available online and come in a nice variety of different metals and sizes for you to choose from.

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The Pocket Square (Handkerchief) - Even Wise Guys Can Get a Runny Nose

A handkerchief is more than just a tissue that you can carry around to wipe your mouth with, blow your nose with, or hand off to a misty-eyed dame in distress. While the handkerchief can be used for all of these purely practical purposes, they’re also used as a very important fashion accessory that can add a extra dose of color and style to your already snazzy looking outfit.

This means that you shouldn’t go hiding that swell lookin’ hanky stuffed deep down inside of a pocket where no one can ever see it. This is a nice looking piece of cloth (or silk) which should be sported proudly in the front breast pocket of your finest suit jacket, where all eyes can feast upon it.

There’s an art to keeping your hanky in your pocket, though. You can’t simply cram it in there in a big, ugly wad and expect it to look great. For a hanky to become a “pocket square” (the official name for your pocket handkerchief) it has to be folded just right; and there are plenty of different stylish folds for you to pick from. To find out how to perfectly fold a hanky into a pocket square you can easily do a quick google search for “How to fold a pocket square”. There are plenty of websites online which will assist you. In fact, here's one right now!

Remember, since your pocket square is going to be a visible piece of your suite, you’ll need to find one with the perfect design and color for whatever you’re wearing. One way of doing this is to try finding a handkerchief that closely matches the color and style of your tie.

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The Boutonniere

If you would like a slightly more garish and flamboyant fashion accessory to go with your suit, that will really make you stick out in a prohibition-era town, look no further than a colorful boutonniere.

A boutonniere is a little accessory that’s worn by men and looks like a small flower (and it can sometimes actually be a flower).To wear one, you slip it securely through the lapel buttonhole on your suit jacket so that it pops, adding color and style to your suit much in the same way as a pocket square does. Incidentally, it should be on the left side of your jacket, the same as your pocket square.

Today, you mostly only see boutonnieres worn by teenagers going to the prom, grooms at weddings, or fancy bigwigs at balls, dinners, and whatever else rich people do for fun. Suffice it to say, they’re typically reserved for only special occasions. And while this was mostly true in the 20s as well, it wasn’t quite as unheard of for someone (usually someone very affluent) to wear a boutonniere in their everyday life. On Boardwalk Empire it’s our protagonist Nucky Thompson who is the best example of this, as we see him wearing his various, colorful boutonnieres throughout much of the series.

It should be noted that if you want to wear a boutonniere you should only do so if you’re shooting for a more high class (or tasteless) appearance; either that or if you’re celebrating a special occasion or attending a formal event. And while you in no way have to be on Nucky Thompson’s level to wear a boutonniere, this is certainly not a look for everyone, and it requires quite a bit of confidence to really pull off. But if you just so happen to have that special kind of swag, I say go with it.

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The Pocket Watch - Blingin' Like a Public Enemy

Believe it or not, a gold pocket watch isn't just for old timey train conductors and Christopher Walken’s derriere (crazy, I know). Normal, everyday people actually wear them too! Well, in the 1920s they did at least. Today, with the invention of cellphones and the addition of digital clocks onto all of our daily used devices, the majority of us rarely even have a need to wear a watch (let alone carry around a small timepiece on a chain). But there was a time, way back when, when these little clocks were all we had — and they looked way cool. None more cool than the classic pocket watch, which we see being worn by most male characters in Boardwalk Empire.

Transcending class standings, a pocket watch can be worn by anyone (the rich and poor both needed to keep time, after all) so one should go well with any style of three piece suit you chose to wear. And when worn correctly, attached to your waistcoat (vest), a shiny, chained pocket watch is a terrific and subtle (notice how all of our 20s accessories are based on subtlety) way to garnish your 1920s attire with an added dose of style, class, and — dare I say it — pizazz. It goes especially well with a similarly colored (usually gold or silver) collar bar and pair of cufflinks.

To display your pocket watch on your waistcoat (so that it acts as a decorative piece of jewelry for your midsection), you need to place the watch in one of your vest pockets and then slip the chain through one of lower buttonholes of your wastecoat, pulling it through and then placing the end of the chain into your opposing vest pocket. And presto! Just like that you've now added a nice piece of "bling" to your already OG'd wardrobe.

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The Sleeve Garters - Roll Up Your Sleeves . . . With Class

Granted, we don’t see sleeve garters on Boardwalk Empire quite as often as we do other clothing and accessories on this list (the photo above isn’t even from the show; that’s how difficult it was for me to find a scene where they were included). However, these little sleeve bands were just too perfect of an apparel to this time-period for us to ignore. So let’s consider these a bonus item for your outfit. You definitely don’t need them in order to fully deck out your 1920s attire. But in my opinion, they sure wouldn’t hurt!

Typically associated with old-timey piano players, professional card dealers, visor-wearing accountants, tough-guys severing drinks behind the bars at your favorite speakeasies, and, I don’t know, barbershop quartet singers(?), these sleeve garters were originally used in a practical manner, when men’s untailored sleeve lengths were a little on the long side and needed some custom management. Like our previously mentioned collar bars, sleeve garters aren’t usually quite as much of a necessity with men’s shirts today as they were back then. But, also like our collar bars, that doesn’t make them look any less snazzy; especially if you’re planning on going for full blown authenticity in your prohibition-era 1920s outfit.

Whether you’re actually in need of a pair of sleeve garters or not, these classic accessories for your arms will act as a great looking addition to your bland old dress shirts (especially when accompanied by a swanky waistcoat). Besides, on those hot nights when you've decided to shed that jacket, expose your vest and show off those sleeves, why not have that little something extra there to remind people just how stylish and down with the times you are. Combining your sleeve garters with your collar bar, pocket watch, waistcoat, hat and cufflinks, you can continue giving off your 1920s vibe even after you’ve put away your jacket.

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The Shoes - Filling the Shoes of a 1920's Hood is Easier Than it Sounds...

Never underestimate the importance of a man’s shoes. Now that you’ve got your hair slid back and you’re all fancied up with your three piece suit, your swell new fedora hat, your boutonniere, collar bar, pocket watch, and sleeve garters, it’s time to finish off the ensemble with a brand spanking new pair of era appropriate footwear.

As far as men's shoes of the 1920s go, we’re going to have to ditch the idea of sneakers, sandals and crocs (for the record, you should abandon the crocs anyway). And while a swell pair of plain old work boots or cowboy boots would technically work, for fashions sake, it may be wise to steer clear of them as well. Brogues and Oxfords are where it's at. Other than that, there's not really a whole lot more to say on the matter, other than that two-toned wingtips are your best bet if you're shooting for the snazziest of snazz in traditional gangster style.

And remember: white socks are a real faux pas; stay far, far away. Go for blacks, browns, argyle, or possibly reds, blues, or greens (if you’re confident enough that you can pull them off and you're sure they'll match your outfit). And make sure that they rise above the ankle, as you don’t want your pants rising up, revealing the skin of your leg when you sit down (that’s bad for either the 1920s or today). Oh! And speaking of socks: sock garters may also be a fun (although not at all needed) bonus for your prohibition-era wardrobe. With the advent of those newfangled elastic bands, men’s sock garters (they’re those little black bands that strap around your calf and are used to hold up your socks) are even less of a necessity these days than arm garters — not to mention, almost no one would see that you’re wearing them — but if you want to take your 1920s getup to the extra limit, go ahead and purchase a pair of those as well.

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Sign the Guestbook 7 comments

Dan Sturby 4 months ago

Thanks for this hilarious and well written article. It was so informative and entertaining to read. I kept chuckling to myself all the way through and completely belted out a few great kneeslappers! I really appreciate this style of clothing. People really knew how to dress like a boss back in the day. It's such a shame that people don't dress this way more often. A man in a well Taylored suit will always win immediate respect from me and everyone will notice with a doubt! Fantastic article, Thanks for a swell time. Lol

Chris 9 months ago

Great article.

flycatcherrr profile image

flycatcherrr 2 years ago

Lookin' sharp there, fella!

It's a treat to find a detailed guide to men's 1920s fashion that is also so amusing.

WriterJanis2 profile image

WriterJanis2 2 years ago

These are so sharp!

georgepmoola2 profile image

georgepmoola2 2 years ago

The fashions of the day were very elegant. Nice lens.

Merrci profile image

Merrci 2 years ago from Oregon's Southern Coast

Clever lens! Enjoyed the lens and the look.

AnonymousC831 profile image

AnonymousC831 2 years ago from Kentucky

Love this look, great lens.

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