1920s-inspired looks for the 2020s

Dress like Jay Gatsby on a Nick Carraway Budget
Blonde woman in a 1920s-themed women's sporting wear look kicking up her leg with her arms out
(Photo submitted by Sunset Saraid)

Hey, I’m Sunset Saraid, a Madison-based blogger who specializes in vintage-inspired and thrifted fashion. I love a good statement dress and all things retro. You can find me at @sunsetsaraid on Facebook and Instagram. Due to my love of thrifting and vintage, the lovelies at Madison Magazine asked for my expertise in finding 1920s-inspired looks for their Best of Madison Party on April 23 at Garver Feed Mill. Here are a few tips I have for you!

Look 1: Menswear

I love the idea of a menswear-inspired look that would be worn as women’s sportswear for the time. For a sporting look, women could wear knee-length knickers in wool tweed or linen and pair it with knee high socks, a button-down, and lace-up oxfords. Style it with a tie, cap, vest and blazer. This entire outfit was created using items from my own closet.

Blonde woman looking over her shoulder in a 1920s-themed outfit

(Photo submitted by Sunset Saraid)

Blonde woman with tan blazer thrown over her shoulder

(Photo submitted by Sunset Saraid)

Close up of Mary Jane vintage shoes

(Photo submitted by Sunset Saraid)

Close up of a beaded fringed 1920s purse

(Photo submitted by Sunset Saraid)

Outfit Details: Cap, Target; Button-down, Good Style Shop; Pants, Goodwill – Monona; Oxfords, St. Vincent – DePaul Willy Street; Blazer, Goodwill; Fringed beaded purse, St. Vincent DePaul – Willy Street.

Look 2: La Garçonne

For this look, I went with a more typical dress of the era. A midi-length shapeless shift dress with a drop waist was ideal. For a little extra pizzazz, I added a white ribbon, worn below the waist. This era was all about contrasting feminine accessories with the boxy, masculine silhouette, so I paired it with a patterned scarf, clothe hat, bead purse and jazzy oxford heels.

Blonde woman in a black dress with a white belt and a silk scarf around her neck holding a purse outside of the state office building

(Photo submitted by Sunset Saraid)


Close up of an embroidered white purse

(Photo submitted by Sunset Saraid)


Blonde woman in a black 1920s-themed dress holding a beaded purse with a fur stole around her forearm

(Photo submitted by Sunset Saraid)

Outfit details: Cloth hat, St. Vincent DePaul – Willy Street; Drop waist dress, St. Vincent DePaul – Willy Street; Faux fur stole, Goodwill; Beaded purse, Goodwill; Metallic oxfords, Modcloth.

Look 3: Flapper

This outfit is inspired by the typical flapper aesthetic. Dresses of the time would be knee-length or longer and have a looser cut, such as a slip dress. Most evening flapper-style dresses were silk, velvet, crêpe or satin and might include elaborate beading or embroidery. I paired this twirl-worthy dress with long black gloves, an art deco-inspired headpiece and my trusty metallic oxfords. It’s sure to turn heads during a night on the town!

Blonde woman striking a pose in a flapper dress outside of the state office building

(Photo submitted by Sunset Saraid)

Blonde woman in a flapper dress looking up with her hand on the side of her face

(Photo submitted by Sunset Saraid)

Outfit Details: Art deco headpiece and gloves, Amazon; Flapper dress, Unique Vintage; Metallic oxfords, Modcloth.


The ladies of the 1920s used a lot of unique accessories to enhance their outfits. Cloth hats, turbans or headpieces are all appropriate. Finish the outfit off with a velvet, fringe shawl or a fur stole. Another option would be long gloves paired with a sleeveless dress. Low-heels in the styles of single-strap Mary Janes, T-straps or oxfords would be most fitting. Luckily, these seem to be fairly easy to find since they came back in style throughout the 20th and 21st centuries. I found my black Oxfords heels at St. Vinnys on Willy Street this fall.

Makeup to go with the look

Blonde woman in a 1920s flapper dress holding a big red paper Valentine

(Photo submitted by Sunset Saraid)

Eyebrows: Thin and arched
Cheeks: Rosy, dark metallic smokey eye
Lips: overdrawn with emphasis on the cupid bow, dark lip in a cherry or blood red

I had a blast putting together these outfits from all my favorite spots in Madison. I highly recommend checking out the Madison-area Goodwills, St. Vincent de Paul stores, Ragstock and Good Style Shop for all of your speakeasy-inspired outfit necessities. Enjoy some giggle water and celebrate 2020’s Best of Madison at Garver Feed Mill on April 23. Click here for more event info and to buy tickets today!

I’ll also be creating a style rack the week before the Best of Madison party at St. Vincent de Paul – Williamson Street, so check that out for last-minute outfit items! Hope to see you at the party. For more vintage inspiration, follow me at @sunsetsaraid.