1920s Men’s Fashion: Complete Guide

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There is always something bold about 1920s men’s fashion. From Chicago gangsters to The Great Gatsby, this is a truly an era that our modern culture holds to great acclaim.

This is reflected in a huge amount of media surrounding a very visually stimulating decade – the aforementioned Gatsby, Peaky Blinders, Downton Abbey, Boardwalk Empire and Midnight in Paris are just a few films set in the time with beautiful 1920s men’s fashion.

Because of this today’s modern clothing is often inspired by 1920s men’s fashion. That means finding 1920s mens fashion for sale is actually quite easy when you need a formal Gatsby outfit or a gangster costume for a 1920s party.

While 1920s fashion for women centers on the iconic flapper dress and lots of rouge 1920s makeup, for men the look is more about classic tailoring.

1920s Men’s Suits


In the 1920s the man’s suit still paid some homage to its Victorian origins and so you should look for high collared suits with three to four buttons up the front. This has not been fashionable for a long time compared to big long lapels that fasten at the waist and so can be challenging.

More workwear styles of clothing tend to favour this as opposed to modern business suits, and this works well for a Peaky Blinders costume. Waistcoats are much easier to find with this sort of cut – and needless to say you want to aim for a three piece suit for a 1920s look.

Trousers should be baggy, or at least a straight cut. Today the fashion is much slimmer, as well as a much lower waist with trousers designed to perch on the hips rather than hang neatly from the waist.

All these challenges mean finding a 20s suit is almost impossible and so you should either make do with the best you can – because no one is really going to see the difference unless they are a fashion historian – or go with a more dressed down look of shirt, suspenders and trousers that we explore further on.

The Hanayome suit pictured is actually a good compromise and a beautiful three piece suit. The cut isn’t too far off and the fabric is 80% cotton.

The next important consideration is fabric. Ideally you want a natural wool or cotton material – not just to avoid the problems with synthetics in fast fashion but to more accurately match the fabrics of the time.

Without central heating, fabrics were also thicker. Suits would look very different to the thin shiny polyester blends you see on high streets today made for hot offices.

1920s Evening Wear

When it comes to men’s 1920s fashion, evening wear is actually a much easier option as the recently invented “tuxedo” dinner jacket and it’s ancestor the tailcoat both featured large sweeping lapels and this style has mostly continued to this day.

Therefore a modern black tie tuxedo suit will often have some resemblance to its 1920s equivalents. The style of tuxedos basically changes from season to season so you need a bit of luck to get a more 1920s style.

It’s always worth checking Macy’s and Nordstrom. Sometimes you can get coloured velvet evening jackets inspired by 1920s smoking jackets. You can wear these with black tie just like a tuxedo.

Rudolph Valentino in black tie with a separate wing collar

However, be warned that turning up to an event in black tie can make you just look like you are wearing black tie rather than a specifically 1920s costume.

You can help this if you go the extra mile and wear a wing collar and cufflinks and maybe accessorize with a white silk scarf, white gloves, cane and hat.

We cover 1920s men’s hats later but for black tie you should wear a homburg while for white tie with a tailcoat you should wear a top hat.

LILIS tailcoat suit

What is the difference between black tie and white tie? Black tie simply means a black bow tie and a dinner suit and was worn for most evening events for the middle class.

White tie meant a white bow tie, white waistcoat and tailcoat and was the more formal option for events like the Opera.

1920s Men’s Shirts

As for shirts, men wore shirts with detachable collars and cuffs. That is because these would wear out and need replacing and just replacing those was easier than the full shirt.

They were also the parts that showed and so would often be starched to create a crisp white finish. These are available from some suppliers and the recent vintage fashion trend has certainly helped traditional collarless shirts – often called “Grandad shirts” make more of a comeback – although these often don’t have holes for the studs used to rivet the collars on and are just meant to be worn collarless.

Read more about collarless shirts and view our top picks here.

However, for most purposes you should be fine with a soft fold-down collar – just avoid those with a wide spread.

For less of a suited look, a collarless shirt with braces and high-waisted trousers makes a great everyday 1920s look. Pair these up with some men’s dress boots and you’ll look great without looking too formal or “dressed up”.

Another iconic look to aim for is the spearpoint collar with a collar clip.

Again for evening wear you’ll want a wing collar shirt which are readily available. The ultimate choice would be a detachable starched collar but a normal wing collar shirt fulfils much of the look for a lot less effort.

Actor Gary Cooper at college in 1922

When it comes to braces – or suspenders – go for button braces and not clip-ons. Not only do clip-ons look unconvincing, they struggle to grip your trousers and come off all too easily. Although Crookhorn Davis actually offer “no sew” clips disguised as buttons.

You can easily sew some buttons onto any pair of trousers. Sew buttons on the waistband just slightly further in than the pockets – it can be on the outside or the inside – and then measure about three inches inwards for the other two. Next sew two at the back at the seam, again about three inches apart.

1920s Men’s Hats

Dorfman Pacific Fedora

1920s men’s fashion definitely required hats. It is only very recently that hats have fallen out of fashion. Historically they were an important accessory to shelter the wearer from the elements and keep hair covered from the smoke of the city.

The ultimate 1920s men’s hat has to be the trilby and fedora. While these are often sold on high streets today they tend to have very narrow brims when in the 1920s men’s trilbies would have at least two inches of brim.

A fedora is simply a trilby with a wider brim like Indiana Jones. These were made of rabbit fur felt, which today is reserved for high end premium fedoras. On the other hand you can get wool felt hats very cheaply.

A good rule of thumb is to match the hat to the shoes – sticking to brown or black – although gray can also look amazing. There’s also the boater for a Great Gatsby costume.

Of course if you’re sticking to a rugged Peaky Blinders outfit then go for the eponymous flat cap or baker boy cap.

Levine homburg

Other styles to consider are the bowler – which was more formal – and it’s cousin the homburg which has a dent running along the top. These were hard hats made from stiffened fur felt.

Men’s 1920s Hairstyles

Buster Keaton

The 1920s hairstyle for men was very simple: short back and sides. A good barber will be very familiar with this cut. It looks great if you can get the sides nicely faded as well and make sure you leave a good few inches on top.

Tame it with an oil-based pomade like Brylcreem or Black & White to create that shine you always see on old movie stars.

As for 1920s facial hair clean shaven was by far the most popular fashion. Remember 1920s fashion was all about rebelling against the stuffy Victorian principles that had led to the First World War – and that includes big bushy facial hair!

Pencil moustaches were popular but again keep it neat and trimmed. You could also shave 1920s-style with a double edge safety razor to get that smooth look.