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Home » Hair Trends & Inspiration » Vintage / Retro Hair » 25 Great Gatsby Hairstyles: Glamorous 1920s Looks to Try

25 Great Gatsby Hairstyles: Glamorous 1920s Looks to Try

Stepping back into the roaring twenties brings an undeniable sense of timeless glamour and rebellion. The era defined a completely new approach to beauty, trading long restrictive locks for daring chops and sculpted waves. Whether you are attending a themed party, a wedding, or just want to inject vintage elegance into your look, finding the right inspiration is essential. This curated list of 25 great gatsby hairstyles offers everything from iconic finger waves to stunning flapper bobs and dazzling accessories. You will discover how to recreate these classic silhouettes whether your hair is short, medium, or long. Get ready to embrace the drama, the shine, and the undeniable charm of the nineteen twenties. Let us explore these unforgettable vintage looks.

25 Great Gatsby Hairstyles Glamorous 1920s Looks to Try - 25 Great Gatsby Hairstyles: Glamorous 1920s Looks to Try

1. 1920S Finger Wave Bob

1920S Finger Wave Bob - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Nothing captures the essence of the jazz age quite like this iconic sculpted look. The 1920s finger wave bob features sharp S-shaped curves molded flat against the forehead and cheeks, ending precisely at the chin. This style works beautifully on straight or slightly wavy hair, creating a sleek and shiny finish that screams vintage luxury. Styling requires a strong hold gel, a fine-tooth comb, and plenty of patience to mold the waves and let them set completely. The result is a strikingly geometric shape that highlights your cheekbones and eyes perfectly. It remains the ultimate statement for anyone wanting an authentic and recognizable period aesthetic for their next event.

2. Great Gatsby Flapper Updo

Great Gatsby Flapper Updo - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Have you ever wondered how those rebellious flappers kept their hair off the dance floor? The great gatsby flapper updo is the answer, offering a playful yet sophisticated arrangement. This look typically gathers the hair at the nape or crown, featuring loose curls and waves pinned haphazardly for a soft, touchable feel. Decorative elements like sparkling headbands or feathered clips are essential here, anchoring the style while adding dazzling movement. It works wonderfully for medium to long hair, giving the illusion of a shorter cut while maintaining length at the back. This updo effortlessly balances wild dance energy with impeccable vintage glamour for any modern occasion.

3. Marcel Wave Long Hair

Marcel Wave Long Hair - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Imagine cascading waves that catch the light with every turn of your head. The marcel wave long hair style uses heated curling tongs to create deep, alternating crests and valleys, producing a more pronounced and lasting wave than finger styling. Unlike the flat finger wave, this technique adds incredible volume and bounce to lengthy locks, making it incredibly flattering for evening events. You can wear it centered or swept deeply to one side for dramatic effect. The key is ensuring each wave is perfectly spaced and highly glossed with a lightweight serum. It delivers old Hollywood sophistication directly from the roaring twenties to today.

4. 1920S Pin Curl Bob

1920S Pin Curl Bob - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Bouncy and full of life, this cheerful short haircut brings movement to a classic silhouette. The 1920s pin curl bob relies on small, coiled sections of hair pinned flat against the scalp to create tight, distinct ringlets or looser brushed-out curls. Once set and released, the curls frame the face with incredible density and texture, softening the jawline beautifully. This method is excellent for naturally straight hair that struggles to hold a wave, as the cooling process locks in the curl pattern securely. A light spritz of hairspray keeps the bouncy shape intact all night. It is a joyful and energetic take on vintage charm.

5. Gatsby Faux Bob Hairstyle

Gatsby Faux Bob Hairstyle - 25 great gatsby hairstyles - 25 great gatsby hairstyles

What if you want the flapper aesthetic without committing to a major chop? The gatsby faux bob hairstyle offers the perfect solution for long-haired individuals seeking a temporary transformation. By tucking and pinning the lengths underneath, you create the illusion of a blunt chin-length cut. The remaining visible sections are styled into soft waves or finger curls, blending seamlessly into the tucked portion. This clever trick requires bobby pins, a little creative rolling, and some confidence. It gives you the freedom to rock a short look for a special occasion and wake up with long hair the next morning. It is truly the best of both worlds.

6. Roaring Twenties Chignon

Roaring Twenties Chignon - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Elegance meets simplicity in this low-slung, timeless masterpiece. The roaring twenties chignon involves gathering the hair at the nape of the neck and twisting it into a smooth, sophisticated knot. Unlike messy modern buns, this version is highly polished and deliberately sleek, often secured with decorative pins or a subtle comb. It allows stunning backless dresses and statement jewelry to take center stage while keeping the hair neatly contained. Applying a styling cream before twisting helps tame flyaways and enhances the luxurious shine. This look remains incredibly versatile, working brilliantly for formal occasions or an elevated everyday aesthetic inspired by the glamorous past.

7. 1920S Headband Updo

1920S Headband Updo - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Step into the spotlight with a look that embraces bold accessories and structural beauty. The 1920s headband updo centers around a decorative band worn across the forehead, pushing the hair back and creating a beautiful frame for the face. The hair underneath is usually styled in soft curls or tucked into a low roll at the back. Rhinestones, pearls, or intricate beading on the band instantly elevate the entire style, making it festive and eye-catching. This accessory-driven approach is incredibly forgiving, easily hiding any imperfections in your curling technique. It instantly transforms a simple hairstyle into a dazzling themed masterpiece for any celebration.

8. Great Gatsby Short Flapper Cut

Great Gatsby Short Flapper Cut - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Shedding the past never looked so liberating and chic. The great gatsby short flapper cut is a blunt, ear-level bob that rejects traditional long hair entirely. It represents the bold spirit of the modern woman, offering unparalleled freedom and movement. This cut typically features a sharp, straight line all around, sometimes with a subtle undercut at the nape for a sleeker finish. It requires minimal styling effort, looking fantastic simply blow-dried smooth or textured with a light pomade for a slightly messy effect. This sharp and daring cut remains an enduring symbol of independence and an effortlessly cool aesthetic for today.

9. 1920S Cloche Hat Hairstyle

1920S Cloche Hat Hairstyle - 25 great gatsby hairstyles - 25 great gatsby hairstyles

How did women maintain their glamour under those iconic bell-shaped hats? The 1920s cloche hat hairstyle answers this with cleverly adapted cuts and minimal visible styling. The cloche fits tightly over the skull, requiring hair to be cut in a way that naturally tucks beneath the brim. Usually, this meant a sleek bob with the back slightly longer, or hair styled completely flat with deep waves only visible at the very front edges. The hat itself acts as the primary accessory, doing most of the heavy lifting for the overall look. It is a masterful blend of fashion and function that defines cozy winter elegance.

10. Gatsby Deep Side Part Waves

Gatsby Deep Side Part Waves - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Asymmetry brings an instant touch of drama to any vintage ensemble. The gatsby deep side part waves rely on an extreme side parting, sweeping a heavy curtain of glossy waves over one eye. This creates a mysterious and alluring look that beautifully highlights the bare side of the face and neck. It works phenomenally well on bob lengths, adding instant volume and elegant movement to the heavier side. Using a large-barrel curling iron and a strong hold pomade will keep the waves smooth and perfectly in place all evening. This striking silhouette captures the moody, glamorous sophistication associated with the prohibition era flawlessly.

11. 1920S Finger Wave Updo

1920S Finger Wave Updo - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Taking the classic sculpted wave off the shoulders creates an entirely new level of elegance. The 1920s finger wave updo incorporates the iconic S-shaped molds along the crown and sides, while the remaining length is gathered into a graceful low bun or roll. This style is incredibly striking because it combines the rigid, architectural beauty of finger waves with the soft romance of an updo. It demands attention to detail, requiring clips to hold the waves while they dry before pinning the back. The finished product is a highly structured and regal look that works wonderfully for formal vintage events and celebrations.

12. Great Gatsby Juliet Cap Updo

Great Gatsby Juliet Cap Updo - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Channel your inner silver screen starlet with this romantic and ethereal headpiece. The great gatsby juliet cap updo features a close-fitting, highly embellished cap that sits over the crown and back of the head. The hair beneath is usually styled into soft, cascading curls or a low chignon that spills out gracefully from under the cap. Pearls, crystals, and delicate lace on the cap provide intense visual interest, drawing the eye upward. This pairing creates a deeply feminine and historically rich aesthetic. It is an exceptional choice for formal occasions, effortlessly bridging the gap between historical costume and high fashion elegance.

13. 1920S Feathered Flapper Hairstyle

1920S Feathered Flapper Hairstyle - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Ready to make a bold and unapologetic statement on the dance floor? The 1920s feathered flapper hairstyle incorporates oversized, dramatic ostrich feathers or plumes directly into the hair. Often secured within a headband or tucked into a marcel wave, the feathers add incredible height, movement, and a sense of rebellious fun. The base hairstyle is usually a sleek bob or a simple updo, allowing the extravagant feathers to serve as the undisputed focal point. This extravagant look perfectly encapsulates the party-centric spirit of the jazz age. It guarantees all eyes will be on you, making it ideal for highly festive celebrations.

14. Gatsby Sleek Low Bun

Gatsby Sleek Low Bun - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Sometimes the most impactful styles are the most understated. The gatsby sleek low bun focuses on immaculate smoothness and pristine finishing. Pulled tightly back from the face and secured at the nape, this style eliminates any bulk or distraction. A deep side part adds a subtle touch of vintage asymmetry, while a generous application of glossing serum ensures zero flyaways. This minimalist approach highlights your facial features and any statement earrings you choose to wear. It is an incredibly chic and refined option that still fits seamlessly into the aesthetic of the era without needing heavy heat styling tools.

15. 1920S Vintage Pin Curl Updo

1920S Vintage Pin Curl Updo - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Softness and texture take the lead in this romantic arrangement. The 1920s vintage pin curl updo gathers meticulously formed curls into a beautiful, cloud-like configuration at the back of the head. Unlike the sleek finger wave, this look relies on the fluffy, brushed-out volume of pin curls to create depth and interest. Leaving a few tendrils loose around the face softens the overall appearance, giving it an approachable and delicate feel. This style is incredibly durable, as the pinned and cooled curls hold their shape for hours. It is a dreamy choice for anyone wanting gentle vintage texture and timeless appeal.

16. Great Gatsby Curly Bob

Great Gatsby Curly Bob - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Embrace your natural texture with a vibrant haircut designed specifically for bounce and volume. The great gatsby curly bob celebrates dense, springy curls by giving them a structured, chin-length shape. This haircut naturally expands, so strategic layering is essential to prevent the pyramid effect while maintaining a gorgeous rounded silhouette. The twenties vibe comes from the overall shape and the deliberate use of shine products to make each curl look remarkably defined and healthy. It is a lively and playful style that requires minimal daily manipulation. This bob highlights the joyful and energetic side of the iconic era beautifully and confidently.

17. 1920S Side Swept Waves

1920S Side Swept Waves - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Draping your hair over one shoulder creates an effortlessly romantic and sweeping effect. The 1920s side swept waves feature large, loose marcel curls that are all directed to one side, creating a beautiful asymmetrical cascade. This style is incredibly flattering for long and medium hair, as it opens up the neck and collarbone on the opposite side. Securing the hair behind the ear with a vintage comb or sparkling pin keeps the look anchored and beautifully polished. The movement of the waves adds a fluid, graceful quality to your overall appearance. It remains a top choice for elegant evening affairs.

18. Gatsby Flapper Girl Cut

Gatsby Flapper Girl Cut - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Pure rebellion never goes out of fashion. The gatsby flapper girl cut takes the traditional bob to an edgier level, often featuring shorn or tapered napes with slightly longer top layers. This bold cut was the ultimate act of defiance against societal norms, offering women a wash-and-go lifestyle that was previously unheard of. Styling is effortless, often just finger-combing some pomade through damp hair to create a piece-y, lived-in texture. The sharp lines and exposed neck feel incredibly modern even today. It is a fantastic option for anyone wanting a low-maintenance cut with a fierce historical backstory and serious modern attitude.

19. 1920S Barrel Curls Updo

1920S Barrel Curls Updo - 25 great gatsby hairstyles - 25 great gatsby hairstyles

For a truly striking and sculptural appearance, look no further than this magnificent style. The 1920s barrel curls updo uses large, cylindrical curls pinned flat against the head to create a scroll-like effect. These large rolls of hair add impressive volume and architectural interest, making the hairstyle look like a piece of wearable art. Often positioned around the crown or framing the face, the barrel curls are secured invisibly to maintain a flawless clean finish. This highly stylized technique requires strong hold products and plenty of bobby pins. It delivers unmatched elegance and a distinctly high-society aesthetic from the era.

20. Great Gatsby Wrapped Low Chignon

Great Gatsby Wrapped Low Chignon - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Refinement reaches its peak with this meticulously crafted low knot. The great gatsby wrapped low chignon takes the basic bun and elevates it by wrapping a section of hair around the base, concealing the hair tie completely. This creates a seamless, continuous line that looks incredibly expensive and well-executed. Adding a deep side part and sweeping the sides smoothly into the chignon enhances the authentic vintage feel. A light mist of shine spray completes the polished aesthetic. This style is impervious to wind and movement, making it highly practical for long events. It exudes a quiet confidence and mature sophistication.

21. 1920S Crown Braid Updo

1920S Crown Braid Updo - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Intricate weaving brings a soft, bohemian touch to the sharp lines typically associated with the era. The 1920s crown braid updo involves braiding the hair and wrapping it entirely around the head like a beautiful halo. This technique keeps the hair secure while creating a beautiful textural contrast against the smooth, unparted front section. It was a popular choice for women who wanted a practical yet ornate way to manage longer hair. Embellishing the braid with tiny pearls or ribbon elevates the look to pure twenties glamour. It is a stunning option for outdoor or summer vintage-inspired gatherings today.

22. Gatsby Tucked And Rolled Bob

Gatsby Tucked And Rolled Bob - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Dimension and shape combine flawlessly in this dynamic short hairstyle. The gatsby tucked and rolled bob features sections of hair that are literally rolled inward and pinned underneath, creating incredible volume at the ends. This technique gives the illusion of much thicker hair while maintaining the sharp bob outline. The rolls can be placed symmetrically or asymmetrically for dramatically different effects. It is a clever way to add structural interest without using heat tools or heavy product. The result is a bouncy, full-bodied look that feels playful and youthful. It remains an inventive approach to classic twenties styling that always turns heads.

23. 1920S Glamour Wave Hairstyle

1920S Glamour Wave Hairstyle - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Capture the essence of silver screen luxury with these sweeping, dramatic crests. The 1920s glamour wave hairstyle is less rigid than the finger wave, focusing instead on large, fluid movements that cascade beautifully. This style often features a deep side part with the waves flowing over one shoulder, creating an aura of absolute opulence. Achieving this look requires large hot tools and careful brushing to soften the curls into connected waves. A high-shine finishing spray is absolutely crucial to achieve the liquid metal effect seen in old photographs. It is the ultimate expression of pure, unadulterated vintage luxury and elegance.

24. Great Gatsby Accessorized Updo

Great Gatsby Accessorized Updo - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Sometimes the hair serves as a canvas for breathtaking ornaments. The great gatsby accessorized updo is defined by its lavish use of jewels, headbands, combs, and pins. The underlying hair is styled into a simple chignon or French twist, providing a clean and secure base. The real magic comes from the placement of sparkling hair jewelry that catches the light with every subtle movement. This approach allows for immense personal creativity, letting you customize a basic updo into a spectacular themed masterpiece. It is the easiest way to guarantee your look feels authentic to the extravagant and prosperous roaring twenties era.

25. 1920S Short Waved Bob

1920S Short Waved Bob - 25 great gatsby hairstyles - 25 great gatsby hairstyles

Short, structured, and undeniably sharp, this haircut remains a staple of the decade. The 1920s short waved bob brings texture to ear-length hair by incorporating small, uniform waves throughout the entire cut. Unlike the flat finger wave, these waves are slightly lifted, adding necessary volume to a very short style. This creates a softer, more approachable look while retaining the sleek geometry of the bob. Using a small curling iron and a styling mist will help achieve this consistent texture easily. It is a brilliant choice for anyone wanting an authentic period look that is manageable and timelessly fashionable every day.

Conclusion:

Embracing the elegance of the roaring twenties allows you to step into a world of unmatched glamour and bold self-expression. This collection of 25 great gatsby hairstyles proves that the iconic looks of the past still hold incredible relevance and beauty today. Whether you prefer the sharp geometry of a finger wave or the romantic softness of a pin curl updo, there is a vintage style perfectly suited for your hair length and texture. Adding authentic accessories like headbands or sparkling pins instantly elevates any of these looks into something truly spectacular. Have fun experimenting with these timeless silhouettes and bring a piece of jazz age magic into your modern life.

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About Jen Atkin

I'm Jen Atkin, a hairstylist who's all about making hair care and styling simple and accessible for everyone. Every day on Lovelyish.com, I share my latest finds and personal tips on the newest hairstyles, cuts, and products. Whether you're looking for a fresh look or ways to keep your hair healthy, I've got you covered with straightforward advice drawn from my years of experience in the industry. Let's make every day a good hair day together!

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