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Home » Hair Trends & Inspiration » Vintage / Retro Hair » 25 Chic 1920s Hairstyles for Long Hair With Headband

25 Chic 1920s Hairstyles for Long Hair With Headband

Stepping back into the roaring twenties has never been easier, especially with these 25 1920s hairstyles for long hair with headband options that blend vintage charm with modern length. The jazz age is famous for bobs and flappers, but long hair can absolutely capture that iconic Gatsby glamour. By adding a beautiful headband, you instantly transform flowing locks into a masterpiece of vintage fashion. Whether you want a dramatic faux bob, elegant Marcel waves, or a romantic braided updo, a headband pulls the whole look together perfectly. You do not need scissors to embrace this classic era. Get ready to discover stunning, authentic roaring twenties looks that keep your length intact and make you the star of any event.

25 Chic 1920s Hairstyles for Long Hair With Headband - 25 Chic 1920s Hairstyles for Long Hair With Headband

1. Finger Wave Faux Bob With Headband

Finger Wave Faux Bob With Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

Have you ever wanted the bob look without losing your length? The finger wave faux bob with headband gives you that classic flapper shape while keeping your long hair safely tucked away. You simply pin your hair under at the nape of your neck to create the illusion of a short cut. Then, mold those iconic S-shaped waves framing your face. A sparkling or silk headband sits perfectly across your forehead, holding the waves in place and adding authentic jazz age flair. This look is incredibly elegant and works wonderfully for themed parties or weddings. You get the best of both worlds with the dramatic short hair vibe and the hidden length. It is a timeless choice that always turns heads.

2. Marcel Wave Low Chignon With Beaded Headband

Marcel Wave Low Chignon With Beaded Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

Picture a glamorous evening out with a sleek low chignon at the back. The Marcel wave low chignon with beaded headband brings serious sophistication to long hair. You create smooth, deep waves on the sides using a curling iron, then gather the rest into a soft, low bun at the nape. The beaded headband slips right over the waves, adding just the right amount of shimmer and keeping the hair out of your face. This style feels very polished and refined. It works brilliantly for formal events where you want an elegant vintage touch. The contrast between the sleek side waves and the textured bun looks stunning. You will feel like true royalty with this beautifully crafted and classic roaring twenties hairstyle.

3. Loose Flapper Curls With Feathered Headband

Loose Flapper Curls With Feathered Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

Nothing says jazz age quite like bouncy, loose curls paired with a bold accessory. The loose flapper curls with feathered headband offer a fun and lively look for long hair. You can use a large barrel curling iron to create soft, voluminous curls all over. Let them cascade down your shoulders naturally. The feathered headband sits across your forehead, instantly transporting you to a vibrant speakeasy. This style is much more relaxed than strict finger waves, making it great for dancing the night away. The feathers add playful movement that matches your bouncy curls perfectly. You will love how effortless yet thematic this look feels. It captures the true party spirit of the era while showing off your gorgeous long locks.

4. Side Swept Long Curls With Lace Headband

Side Swept Long Curls With Lace Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

Looking for something soft and incredibly romantic? The side swept long curls with lace headband deliver a dreamy vintage vibe. You curl your long hair into flowing ringlets, then brush them out gently for a soft wave. Pull all of that beautiful hair over one shoulder to create an asymmetrical and dramatic silhouette. A delicate lace headband sits right at the hairline, offering a subtle and feminine detail that does not overpower the curls. This look is perfect for outdoor events, garden parties, or a romantic evening. It feels very ethereal yet still firmly rooted in 1920s fashion. You will enjoy how the lace softens the overall style while the sweeping curls make a gorgeous, unforgettable statement.

5. Braided Crown Updo With 1920s Headband

Braided Crown Updo With 1920s Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

How do you combine boho charm with jazz age glamour? The braided crown updo with 1920s headband does exactly that. You braid two sections of your long hair and wrap them around the top of your head like a crown. This keeps your hair secure and creates a lovely textured base. Then, you place your favorite 1920s style headband right over the braids. This could be a crystal, bead, or sequin band that contrasts beautifully with the soft braids. The rest of your hair stays tucked in or flows freely underneath. It is a fantastic way to keep long hair off your neck on a warm day. You get a unique look that blends different eras seamlessly and stays put all day.

6. Deep Side Part Waves With Chain Headband

Deep Side Part Waves With Chain Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

A dramatic part can change your entire look. The deep side part waves with chain headband offer striking asymmetry that defines the 1920s aesthetic. You part your hair far to one side, sweeping the larger section over in a glorious wave. Using a curling iron, you craft smooth, deep waves that fall beautifully over one eye. A metallic chain headband rests just above the hairline, adding a modern yet vintage edge. The chain catches the light perfectly as you move. This style works exceptionally well for long hair because the heavy side sweep uses the length to create stunning volume. You will look absolutely captivating with this bold, glamorous, and slightly mysterious look that channels the ultimate flapper energy.

7. Rolled Under Faux Bob With Silk Headband

Rolled Under Faux Bob With Silk Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

Tucking your hair under creates a flawless short hair illusion. The rolled under faux bob with silk headband is a clever trick for long hair. You simply roll the ends of your hair under themselves at the nape of your neck and pin them securely. This creates a smooth, blunt bob shape. Add a luxurious silk headband that matches your outfit for an authentic touch. The silk feels incredibly comfortable against your scalp and looks very elegant. This style is perfect when you want a sleek, clean look without any flyaways. It stays neat all day long and gives you that iconic twenties silhouette. You will appreciate how simple it is to achieve such a dramatically different and polished vintage appearance.

8. Vintage Hollywood Waves With Crystal Headband

Vintage Hollywood Waves With Crystal Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

Want to feel like a movie star from the silver screen? The vintage Hollywood waves with crystal headband bring ultimate old school glamour to long hair. You create large, shiny waves that cascade elegantly over your shoulders. The key is making the waves smooth and seamless, using lots of shine spray. A sparkling crystal headband slips right in, acting like a beautiful tiara for your vintage look. This combination is breathtaking for formal occasions, galas, or holiday parties. The crystals reflect the light and draw attention to your glowing face and gorgeous hair. You will feel incredibly luxurious and sophisticated. It is a head turning style that proves long hair can perfectly capture the magic and elegance of the roaring twenties.

9. Half Up Finger Waves With Long Curls And Headband

Half Up Finger Waves With Long Curls And Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

Sometimes you want the best of both worlds. The half up finger waves with long curls and headband give you exactly that. You style the top half of your hair into those classic, sculpted finger waves around your face. The bottom half remains free, flowing into beautiful, bouncy curls down your back. A decorative headband bridges the two sections perfectly, holding the waves tight while adding a dash of sparkle. This look is fantastic because it highlights the iconic 1920s element while fully embracing your long hair. It feels very festive and lively. You will love how the structured waves contrast with the free flowing curls. It is a stunningly unique style that stands out in any crowd.

10. Low Bun With Swirl Waves And Headband

Low Bun With Swirl Waves And Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

A low bun does not have to be boring. The low bun with swirl waves and headband turns a simple style into a work of art. You carve gentle, swirling waves into the front sections of your hair. Then, you gather the length into a smooth, elegant low bun at the back. A gorgeous headband slips over the swirls, framing your face and adding instant twenties charm. The swirl waves add incredible visual interest to the front, while the bun keeps the back neat and sophisticated. This is a wonderful option for warmer weather or active events where you want your hair up but still styled. You get a classy, refined look that feels timeless and completely authentic.

11. Gatsby Inspired Long Waves With Gold Headband

Gatsby Inspired Long Waves With Gold Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

Gold instantly elevates any vintage look. The Gatsby inspired long waves with gold headband scream pure luxury and excess. You style your long hair into soft, glamorous waves that fall naturally. Then, you add a stunning gold headband that sits right at the hairline. The gold catches the light beautifully and adds a rich, opulent feel to the entire hairstyle. This look is incredibly easy to achieve but looks incredibly expensive. It is perfect for a Gatsby themed party, a New Year celebration, or any fancy night out. The warm gold tone works beautifully with any hair color. You will feel like you just stepped out of a roaring twenties mansion, ready for a night of dancing.

12. Pinned Side Curls With Rhinestone Headband

Pinned Side Curls With Rhinestone Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

Sweeping your hair to one side creates instant drama. The pinned side curls with rhinestone headband offer a very elegant and sparkling vintage look. You curl your long hair entirely, then gather all of it and pin it gracefully over one shoulder. Let a few curls fall loose to frame your face. Next, place a dazzling rhinestone headband across your forehead. The rhinestones add intense sparkle and draw all the attention upward to your eyes. This asymmetrical style is incredibly flattering and makes your hair look thick and voluminous. It is a great choice for formal events where you want to look your absolute best. You will feel stunning, glamorous, and completely ready for the spotlight.

13. Center Part Wavy Long Hair With Bandeau Headband

Center Part Wavy Long Hair With Bandeau Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

A center part offers a different kind of twenties style. The center part wavy long hair with bandeau headband feels very authentic to the era. You part your hair down the middle, creating soft, natural waves on both sides. A bandeau headband wraps around your head, often tying at the back or slipping over the top. This style is more relaxed and bohemian, perfect for casual daytime events or outdoor garden parties. The bandeau keeps the hair out of your face while adding a lovely vintage accent. You will enjoy how comfortable and effortless this look feels. It proves that you do not need heavy styling to capture the essence of the jazz age with your beautiful long hair.

14. Vintage Spiral Curls With Pearl Headband

Vintage Spiral Curls With Pearl Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

Pearls add a touch of delicate elegance to any era. The vintage spiral curls with pearl headband create a soft, romantic look. You use a small curling iron to create tight, bouncy spiral curls all over your long hair. Then, you gently brush them out slightly for more volume. A delicate pearl headband sits right at the hairline, adding a beautiful luminous glow. The pearls complement the spirals perfectly, creating a very feminine and sweet aesthetic. This style is wonderful for weddings, tea parties, or any springtime event. You will love how the spirals bounce and move, while the pearls keep the look anchored in the 1920s. It is absolutely charming and wonderfully graceful.

15. Side Swept Ponytail With Finger Waves And Headband

Side Swept Ponytail With Finger Waves And Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

Ponytails can be vintage too! The side swept ponytail with finger waves and headband is a clever twist on a classic. You create sleek finger waves at the front and sides of your hair. Then, you gather the rest of your long hair into a low ponytail that drapes over one shoulder. A beautiful headband sits over the finger waves, keeping them neat and adding sparkle. This look is surprisingly practical while remaining completely authentic to the jazz age. The finger waves give you that strict twenties vibe, while the ponytail uses your long hair in a fun way. You will find this style very comfortable and secure for a long night of dancing.

16. Loose Updo With Face Framing Waves And Headband

Loose Updo With Face Framing Waves And Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

Updos do not have to be tight and stiff. The loose updo with face framing waves and headband offers a soft, romantic approach to 1920s hair. You pin your long hair up loosely, letting a few tendrils escape for a relaxed feel. The most important part is the face framing waves. You sculpt soft, wide waves around your face to create that vintage shape. A simple but elegant headband holds the waves back slightly and adds definition. This look is perfect for someone who wants an authentic feel but prefers a softer, more approachable style. You will look effortlessly beautiful, as if you just threw your hair up and still managed to look like a twenties starlet.

17. Double Pin Curl Updo With 1920s Headband

Double Pin Curl Updo With 1920s Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

Pin curls are a staple of vintage styling. The double pin curl updo with 1920s headband uses them as the star of the show. You create two symmetrical pin curls right at the front of your hair, framing your forehead beautifully. The rest of your long hair is pulled back into a neat, elegant updo. A striking 1920s headband slips right between the pin curls and the updo, bringing the whole look together. This style is very striking and architectural. It shows off your styling skills and creates a very authentic flapper look. You will feel like a true vintage vixen with this bold, structured, and incredibly chic hairstyle that highlights your facial features perfectly.

18. Vintage Twist With Headband And Loose Tendrils

Vintage Twist With Headband And Loose Tendrils - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

Combining twists and loose pieces creates beautiful texture. The vintage twist with headband and loose tendrils gives you an effortlessly elegant look. You twist sections of your long hair back and pin them securely, creating a beautiful woven effect at the back. You intentionally leave a few soft tendrils out around your face and neck. A classic headband sits at the crown, adding that necessary 1920s detail. The contrast between the structured twist and the soft tendrils is very romantic and flattering. This style is perfect for a vintage inspired wedding or an evening out. You will love how the loose tendrils soften your face while the twist keeps your long hair perfectly managed and beautifully styled.

19. Waterfall Waves With Sequin Headband

Waterfall Waves With Sequin Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

Let your long hair flow with stunning movement. The waterfall waves with sequin headband create a breathtaking effect. You curl your hair into long, cascading waves that ripple down your back like a waterfall. The waves should be smooth and continuous. A bright sequin headband rests against your hairline, providing a flashy and festive counterpoint to the flowing hair. The sequins catch every bit of light, making you sparkle from across the room. This look is ideal for parties, celebrations, and New Year bashes. You will feel incredibly glamorous and vibrant. It is a very simple way to wear your long hair down while still committing fully to the dazzling and exciting spirit of the roaring twenties.

20. Voluminous Marcel Waves With Wide Headband

Voluminous Marcel Waves With Wide Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

Sometimes, bigger is better. The voluminous Marcel waves with wide headband deliver maximum impact. You use a large barrel iron to create deep, dramatic Marcel waves that have tons of body and lift. The wide headband sits further back on your head, helping to push volume at the roots while adding a bold accessory. This style is all about glamour and making a statement. The wide headband covers more surface area, giving you a very luxurious and rich look. It is perfect for a theatrical event or a high fashion vintage shoot. You will command attention with this powerful and striking hairstyle that uses your long hair to create the most incredible shape and movement.

21. Tucked Low Roll With Beaded Headband

Tucked Low Roll With Beaded Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

A tucked low roll is incredibly chic. The tucked low roll with beaded headband is a sophisticated way to manage long hair. You roll your hair inward at the nape, creating a smooth, cylindrical shape that sits right at the base of your neck. A beautifully beaded headband slips over the top of your head, adding shimmer and keeping the front sleek. This style is very neat and secure, making it perfect for windy days or active dancing. The beads add just enough interest without making the look too fussy. You will appreciate how polished and put together you look with this classic updo that perfectly balances the sleek roll with the sparkling twenties headband.

22. Long Hair Finger Wave Updo With Headband

Long Hair Finger Wave Updo With Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

You can create an updo entirely out of waves. The long hair finger wave updo with headband is a masterpiece of vintage styling. You sculpt your long hair into finger waves all the way down, then carefully pin them up into a beautiful, undulating updo. The waves wrap around each other, creating stunning depth and texture. A simple headband anchors the front, keeping the waves tight against your forehead. This look requires some patience but the result is absolutely breathtaking. It is a true work of art that belongs in a vintage fashion museum. You will feel incredibly elegant and unique, knowing you are wearing a highly skilled and authentic 1920s hairstyle that showcases your long hair perfectly.

23. Great Gatsby Long Loose Waves With Headband

Great Gatsby Long Loose Waves With Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

The Great Gatsby look is all about effortless luxury. The Great Gatsby long loose waves with headband capture that perfectly. You create soft, touchable waves in your long hair, letting them fall naturally and freely. The headband should be elegant but not overbearing, perhaps a thin chain or a subtle crystal band. This style is less about stiff styling and more about looking effortlessly wealthy and relaxed. It works for both formal and casual vintage events. You will look like you just stepped off a yacht, sipping champagne in the sunshine. It is a wonderfully versatile look that proves you do not need a complicated updo to embrace the roaring twenties with your long, beautiful hair.

24. Vintage Long Hair With Cloche Hat And Headband

Vintage Long Hair With Cloche Hat And Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

Cloche hats are iconic, but they need a headband. The vintage long hair with cloche hat and headband uses both for ultimate authenticity. You tuck your long hair behind your ears, letting it flow out from under the bell shaped cloche hat. A ribbon headband wraps around the hat, or you wear a separate band underneath. This look is incredibly cute and practical for cooler weather. The cloche frames your face beautifully, while the headband adds a lovely decorative touch. You will feel like a true 1920s pedestrian, walking down the avenue in style. It is a charming and historical look that protects you from the cold while keeping your long hair perfectly styled and vintage appropriate.

25. Elegant Low Chignon With Wave Detail And Headband

Elegant Low Chignon With Wave Detail And Headband - 25 1920s hairstyles for long hair with headband - 25 1920s hairstyles for long hair with headband

Closing out our list is a timeless classic. The elegant low chignon with wave detail and headband is the perfect finish. You gather your long hair into a smooth chignon at the nape of your neck. The special touch is the wave detail. You carve a few deep waves into the front section of your hair before sweeping it back. A gorgeous headband sits over the waves, adding sparkle and keeping them intact. This style is the epitome of twenties elegance. It is perfect for brides, bridesmaids, or anyone attending a very formal event. You will feel sophisticated, graceful, and completely stunning with this beautifully balanced look that honors the golden age of glamour.

Conclusion:

Embracing the jazz age has never been more achievable for those with lengthy locks. These 25 1920s hairstyles for long hair with headband prove that you do not need a sharp bob to capture the magic of the flapper era. From faux bobs and elegant chignons to cascading waves and braided crowns, the options are truly endless. The simple addition of a headband instantly transforms any long hairstyle into a roaring twenties masterpiece. Whether you prefer heavy sparkle, delicate lace, or bold feathers, there is a perfect headband waiting for you. Try out these incredible vintage looks for your next themed party, wedding, or special event. You will undoubtedly turn heads and feel like a true Gatsby star wherever you go.

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Vintage / Retro Hair

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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