If you’ve seen the 2013 film The Great Gatsby then you know that Leonardo DiCaprio is the actor who portrays Jay Gatsby and his larger-than-life character . The movie was filmed using plenty of beautiful colors and depicted a scene where people celebrate the times. Many people yearn to live like Gatsby, traveling the world and partying. Yet, they can at least learn to dress just like him and act like him. So let’s show you how to replicate The Great Gatsby look through fantastic menswear choices.

Why Dress Like Jay Gatsby?

The roaring 2020s have arrived. We’ve had many challenges in the past year with all this craziness going on, but it’s also important to remember that we’re alive and the best is yet to come. For this reason many people are reviving the dress styles of the 1920s and having events called Gatsby parties, also sometimes called Prohibition parties. The times that we live in are worth celebrating, despite all of the challenges that we have faced this year. So perhaps you might be planning to attend a Great Gatsby Party. The first thing on your mind might be: What do you wear to a Great Gatsby themed party? This is an excellent opportunity for you to let your creativity and passions shine a light through your personal style.

During the 1920s, life was changing fast and improving for ordinary people – with new advances and technology promised a better future. In real like the men that Jay Gatsby was inspired by emerged as new figures who was known for being renaissance men. People were living in exciting times, and so people were looking to set new standards and let loose a bit. We’re at that point now again, where we get to see all of the possibilities of AI and other technologies. So even though the 1920s were 100 years ago, we still have similar things to celebrate. If you’re preparing to have a roaring twenties party in the 2020s, here are some solid fashion tips which can help you celebrate the occasion with our Great Gatsby style guide. 

Your Style Choices Matter – What Is The Great Gatsby Dress Code?

The first order of business of this “Great Gatsby Style Guide” is if you are aspiring to join the ranks of the “Great Gatsby men,” you should remember that you should focus on making smart style choices that are designed to attract attention to you and make people think that you resemble The Great Gatsby himself. 

 There’s no specific dress code in the Great Gatsby, but most people are generally looking to put forth their best image. People wear many different outfits in the movie, and they are all designed to project the image of success and the desire to impress others.

The Great Gatsby men from the film are idealized examples of how men dressed in this era yet it is true that men from the 1920s and 30s were known for their sense of style and sophistication, so you need to keep that in mind. Modern day “Great Gatsby Men” also know the value of style, charm, and having a solid reputation for being fun and outgoing.

How Do You Dress Like Jay Gatsby From “The Great Gatsby”? 

What did Jay Gatsby wear?

If you are a fan of the movie there’s a chance that you probably admire the sense of style and sophistication of the clothing that Leonardo DiCaprio wore to create the image of Jay Gatsby. So here’s a quick guide on how you can dress just like Gatsby.

 The way Leonardo DiCaprio portrayed the Great Gatsby menswear in the movie was often according to the occasion. But, one can also be assured that The Great Gatsby was always well dressed no matter what the occasion or the weather conditions.

 He would often be seen wearing some form of a Art Deco style suit, which isn’t surprising given the parties that he would attend. This type of suit is sometimes called today as a “Great Gatsby Suit”. The Art Deco style suit typically was of a pattern that is designed to stand out and draw attention. In the books and film Jay Gatsby is always known for making a bold statement, whether it’s through his fashion choices or through his lavish parties. Modern day “Great Gatsby Men” should keep that in mind when making their choices for the outfit they would like to wear to a party.

If you follow our advice and pick one of these outfits you’ll make other people think that you’re someone special and that you might even be the hos who runs the party. Style is definitely one of the defining traits of Jay Gatsby, so it’s best to learn to emulate his style if you’re planning to attend a Gatsby party.

As a tip you should probably order the sizes just a’bit larger than you would and then take the suits to a tailor near you for a more custom fitting. This is what will get you the best results.

Jay Gatsby style Tuxedos

One of the trademark looks that Gatsby wore is a tuxedo. This is an outfit that was complete with cufflinks, a bow tie, and of course, black shoes and a handkerchief. Any standard black tuxedo will do, as long as the details such as the handkerchief and cufflinks are present. This isn’t just Great Gatsby menswear, but rather it’s also a timeless look that will persist over the years. The tuxedo below comes in many colors aside from black and any of them will work.

The classic tuxedo is truly the signature Gatsby look because he’s featured wearing a tuxedo suit at one of his parties with fireworks in the background. He has a black jacket, black tuxedo, white shirt handkerchief, and black bowtie. You can also switch the black bowtie for a white one if you prefer.

What kind of shoes to wear to get the Great Gatsby look

Your choice of shoes and the watch you wear also have a significant impact on your style. You cannot go wrong with a pair of leather soled two toned Art Deco style Oxford shoes. It will make you stand out and attract the attention of everyone around you. It’s that finishing touch that creates an outfit that makes you proud to be in public.

You might also consider having custom made bespoke shoes produced for your size. I am a big fan of the shoes produced by Don’s Footwear, and I own several styles of shoes produced by this workshop. Don is one of the best makers of elevator shoes for men, that add a few inches of height. The elevator shoes that Don’s Footwear crafts have a special midsole insert that keeps your foot flat and allows you to walk normally (you don’t feel like you are wearing women’s heels). As a man who is on the shorter side and who enjoys dressing well, I frequently wear one of my pairs of shoes produced by Don’s.

Jay Gatsby style canes for a gentleman

In the film Jay Gatsby has a very unique walking stick as part of his outfit. Historically men who fancied themselves as gentlemen wore a cane with their outfits although this tradition has been lost over the generations. Today it is difficult to find high quality stylish canes as they are much less commonplace now and what is normally found are cheaply made costume canes. But we located some high quality handmade canes which we are listing below for you to browse. While these don’t have the same style as the cane used by Leonardo DiCaprio in the The Great Gatsby movie they will match your outfit.

Through the film Jay Gatsby often carried his cane with. It becomes a part of his mannerisms and gestures, as he used the cane to point at others and draw attention to himself. The cane is a classic sign of sophistication, which allows a man to add a bit of swagger to his step. It’s a standard accessory, which is also a great sign of wealth.

What Colors Should a Man Wear to A Great Gatsby Themed Party When Outdoors?

When you are outdoors, you might choose a slightly different style for your formal wear. You might consider wearing lighter colored outfits because it’s the perfect attire for the summer heat. It’s also a nice distinction, and it’s something that you would expect a person with a sense of sophistication to wear. So you can purchase your suits in several different colors for different seasons and events you expect to participate in.

Consider choosing an ivory-colored suit with a solid colored shirt for outdoor summer events. The white ivory suit is also a classic Great Gatsby suit look because it features plenty of gorgeous pleating.

Gatsby’s classic look was a tuxedo, but there is one scene in the movie where he went to a speakeasy with his new friend, wearing a tan-colored suit with a vest, along with a narrow-brimmed straw hat. This is a great outfit because it would have been stylish for a fun occasion in the 20s and today’s times.

 How Should I Dress For A Prohibition Party?

It’s your prohibition party, so how you dress for the party is entirely up to you. But, if you’re looking to replicate the Gatsby style, the easiest thing to do is to wear a tuxedo such as we recommended earlier. Most men of this period would wear a tuxedo to all formal parties. Doing so is sure to make a strikingly great impression on others when you attend the prohibition party.

What about wearing a “Gangster Style” outfit to a Prohibition Party?

If you aren’t necessarily interested in dressing exactly like Gatsby, another choice is to dress like a 1920s gangster which in popular media is always a pin striped suit. This is an effortless outfit to assemble because it can be purchased as a costume off the shelf. It includes a vest, 20s style fedora hat, and tie. While this isn’t how Gatsby would dress, it’s still something that would fit into the occasion of how to dress for a Prohibition Party. 

These “gangster” outfits comes in several different variants, such as this one by VINCI that has a lovely jet black color that is designed to shine, meaning it will stand out.

Don’t Just Imitate Jay Gatsby’s Dress — Adopt his Optimism, Too

Gatsby was is best known for his extravagant parties. But he was also known for having a generally upbeat attitude on life. He always had an infectious, million-dollar smile on his face. He surrounded himself with a circle of friends and even was quick to take new friends under his wing. Among the most prominent of those new friends was Nick Carraway, his neighbor, who moved in to the cottage next to him. Being like Gatsby also means having an endless supply of friends to surround yourself with.

In one scene in the movie, he held a drink in his hand while making a toast to his friends with fireworks in the background. This classic Gatsby scene sums up precisely what Gatsby is known for portraying to his friends, a scene that shows off his level of sophistication and success by raising a glass of champagne up high. 


Again, if you are concerned about if you’ll look too out of place in these 1920s style Art Deco suits then all you need to remember is to do the best you can and be yourself. Having a smile like Gatsby’s, along with a very positive and upbeat attitude, are what made Gatsby himself and is why people admire the character so much. These are personal attributes that don’t cost money, and honestly – even the most excellent suit can’t overcome a bad attitude in life. So you should try to match Gatsby’s level of confidence and charm in your own personality.

Strive to be someone who is always upbeat. The two most important items in your outfit should be a great smile and attitude. That’s something that no Great Gatsby style guide can teach you how to do – you’ll just have to be yourself and let the best sides of you shine out.


Carey Martell is Editor in Chief for The Millennial Gentleman. A thirty something modern man who is politically independent, non-religious but a firm believer in ideals of chivalry and traditional family values. Carey lives his life as a vagabond digital nomad traveling and living life to the fullest while managing his businesses remotely with a laptop and internet hotspot connection.