What To Wear To A Roaring 20s Party

What To Wear To A Roaring 20s Party: 10 Outfits

Last Updated on March 24, 2024 by Kimberlee Johnson

Are you ready to dive into the thrill of embodying a flapper and partying as if we’ve been transported back to the 1920s? Whether your destination is a concealed speakeasy or a party that draws inspiration from the past, there’s truly no experience comparable to a festivity themed around the Roaring 20s.

But if you’re looking for fun and creative ideas for what to wear to a Roaring 20s party, you’re in the right place. 

From classic flapper dresses to modern takes on the era’s style, we will inspire you to make your next party unforgettable. 

So, slip on your dancing shoes, grab your best pals, and let’s get ready to party. 

Top 10 1920s-Inspired Outfits For Men & Women

1. Lace Flapper Dress With Pearl Choker & Feathered Headband

Woman Wearing Flapper Dress

A lace flapper dress with a pearl choker and feathered headband is a stunning look for a roaring 20s party. 

The dress is a timeless combination of sophistication and style, with its intricate lace and long, flowing design. 

Plus, the pearl choker adds a touch of classic glamour, while the feathered headband creates a playful and fun vibe. But what should you wear to a masquerade party?

2. Cream Silk Tea Dress With Tasseled Fringe & Matching Beaded Cloche Hat

This cream silk tea dress is nothing short of luxurious, featuring a classic cut with a flared skirt and a playful touch of tasseled fringe that adds a fun and flirty movement to your every step. 

Besides, the matching beaded cloche hat is the perfect accessory to complete the look, with its intricate beading and matching cream color that exudes sophistication.

3. Silk Drop Waist Dress With Beaded Cloche Hat & Opera Gloves

Step into the jazz age with this incredible outfit. This silk drop waist dress is a showstopper, with a loose and flowy fit that drapes elegantly on your figure, creating a chic look. 

Adorned with exquisite beading, this dress will sparkle and shine with every move you make, making you the center of attention all night long. 

Plus, the matching beaded cloche hat and opera gloves are the perfect addition to this outfit. But what should you wear to a Casino Night party?

4. Sequin Mini Dress With A Feather Headband & Tasseled Shoes

This ensemble has got it all – from the shimmering sequins that embody the glitz and glam of the decade to the playful tassels on the shoes that add a touch of personality. 

And let’s not forget about the feather headband, which adds elegance and fun to the entire look. Check out these outfits to wear on a party bus here.

5. Velvet Sheath Dress With A Fur Collar & A Pillbox Hat

Consider a velvet sheath dress with a fur collar and a pillbox hat if you’re after a timeless and chic look for a roaring 20s party. 

The rich velvet fabric oozes luxury, while the fur collar adds a touch of sophistication and warmth. 

“Fashion you can buy, but style you possess. The key to style is learning who you are, which takes years. There’s no how-to road map to style. It’s about self expression and, above all, attitude.” 

Iris Apfel, American Businesswoman

And, of course, adding a pillbox hat is a great accessory that was all the rage during the era.

Read: 10 Sparkly Outfits To Wear For Mardi Gras Party

6. Pin-Striped Suit & Spats

3 Men Wearing Pin-Striped Suit

This dapper combo will make you feel like a gentleman from the jazz age. The pinstripes add a touch of sophistication to your outfit, while the spats add a playful twist. 

Trust us, the white spats worn over your shoes will make you look like you just stepped off the pages of a Gatsby novel [1].

7. Tuxedo With Bowtie & Tophat

Go full-on Gatsby for your next roaring 20s bash with a tuxedo, bowtie, and top hat ensemble. This classic combo is a timeless look that’ll never go out of style. 

The black tuxedo gives you a sharp and refined appearance, while the bowtie adds a pop of personality. 

And remember the top hat; you’ll feel like the most dapper dude at the party and be the talk of the town. But what to wear to your friend’s Bridgerton party?

8. Tweed Suit With Trilby Hat & Brogue

This relaxed yet stylish getup is perfect for those who want to embody the era’s free-spirited vibe. 

The tweed material gives you a down-to-earth look, while the trilby hat adds an air of mystery. Plus, pairing it with the brogues will surely bring a touch of a traditional class.

But what should you wear to a grad party?

9. Oxford Shirt With Knit Tie & Newsboy Cap

This classic yet trendy look is perfect for the dapper who wants to stand out. 

You’ll seem professional and put together in your Oxford shirt, and your knit tie will give you a unique flair. Top it all off with a Newsboy cap for a touch of playful charm.

10. Gangster Look With Fedora & Derby Shoes

Man Wearing Fedora Hat

Get ready to channel your inner Al Capone at your next Roaring 20s party with a gangster look featuring a fedora and derby shoes.

This daring getup is perfect for those who want to turn heads and make a statement. 

The fedora adds a touch of mystery to your look, while the derby shoes bring a touch of class. Together, they create an outfit that’s equal parts cool and debonair. 


In the 1920s, what colors were popular?

In the 1920s, popular colors included neutral colors such as green, off-white, light blue, pale gold, and light pink. But what exactly is a Speakeasy party?

During the 1920s, what was the popular style of dress?

During the 1920s, the flapper dress was the most popular style. 

The flapper dress was characterized by its short and free-flowing skirt [2] and often had fringe or beading to add extra flair.

Check out these elegant outfits for a debutante ball here.

Key Takeaways

Bring on the glamour and let loose – dress to impress for your roaring 20s party and make the most out of your night.

With some stylish flair, you’ll surely have a memorable time. So put on your best 1920s look, and get ready to party!


Kimberlee Johnson
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