Vintage Glam: 15 Roaring 20s Hairstyles

Whether you’re inspired by Boardwalk Empire’s forever beautiful cast of prohibitionist-era women, films like Fitzgerald’s Great Gatsby or vintage classics such as Dorothy Parker, Gilda Gray or Clara Bow, one fact remains true: women of the 1920s were worthy of admiration. Not just on a fashion and beauty level, but on political and social levels, too. The 1920s represented a surge in “girl power” — it’s when women gained the right to vote, weren’t afraid to cut their hair, play with makeup or even (gasp!) drink and dance.

Today we pay homage to women of the 1920s. Try these roaring 20s hairstyles yourself and try not to feel brazen, emboldened and grand.

Glamorous Hollywood Deep Wave

Glamorous Hollywood Deep Wave hairstyle
 Instagram @brianna.w.hair

Q&A with style creator, Brianna Bacon
Hairstylist / Owner @ Salt And Light Salon in San Marcos, CA

How would you describe this look?

I would describe this look as a glamorous Hollywood deep wave or a vintage Great Gatsby hairstyle.

I admire the fact that we can take trends from the past and wear them in any decade! This is a timeless look that can be styled for just about any event, whether it is a night out or for a themed party.

Any advice for someone considering it?

If you are considering this hairstyle, my advice for achieving a deep wave like this is to take the foundation of styling hair from the past an add a modern twist. In the 20s to 40s setting hair with pin curls and curlers/rollers on wet hair were the key to creating beautiful waves.

Setting our hair is just as important today, but now we can use the heat from our wands or curling irons on dry hair. I recommend using Kevin Murphy’s Anti.Gravity as a product to help this style last all evening.

This look can be worn with almost any hair type. Someone with a natural wave or curl will need to blow dry their hair smooth first. After setting the curls, gently comb through and be the star of any event!

Modern 20s Look

Modern 20s Look hairstyle
 Instagram @pin_up_curl

Q&A with style creator, Sarah Bloor
Freelance Bridal and Vintage Hairstylist @ in Derby, UK


How would you describe this look?

This 20s-inspired look with a more modern, softer feel is one of my favorite styles to create. A large, sharp wave flows down into a curl-covered Gibson roll at the back. True authentic hairstyles from that period could be quite flat to the head, sometimes a little harsh, so making this hairstyle a bit fuller keeps it more up-to-date and flattering.

I love the contrast of the curls against the sharp wave. It’s very pleasing to my eye. It’s also a very adaptable style. The curls and roll can sit along the back of the head, or to one side. The curls can be bigger, smaller, less structured, and more waves can be included.

Any advice for someone considering it?

This is a style that works perfectly on medium to thicker hair, as well as on finer hair, providing it’s longer than the shoulder blades. Obviously the more hair you have the more volume and curls you get.

It’s perfect for a ball or red carpet event, or even a prom. I particularly love it for the bride who wants something different from the softer, tousled, braided styles you see a lot of today. This look is ideal for the bride who loves a classic, timeless look along with some Hollywood glamour. It looks stunning when the dress is off the shoulder or has a beautiful back detail.

You’ll need a small barrel curling tong and there can be several (ok, lots of!) hair grips and pins involved, so it’s all about creating a good foundation for the curls to be placed on. I tend to use a bun ring cut in half to roll the hair around and for the grips to grip into. A pomade or serum is also vital to add smoothness, control, and shine. And to finish it all, I’ll use a salon-quality strong hold hairspray.

Elegant 20s Updo

Q&A with style creator, Amanda Nelson
Hairstylist @ Matthew Robert Salon Inc. in Edmonds, WA


How would you describe this look?

This look is simple and its elegance brings out the 20s inspiration. It is perfect for all hair lengths.

My favorite thing about this look is that it will last all night long. The hair is wound around the headband, allowing her freedom to dance the night away!

Any advice for someone considering it?

My advice is to shop in advance for themed accessories. Go BOLD and have fun!

Platinum Textured Bob

Platinum Textured Bob hairstyle
Instagram @jreneehairnyc

Q&A with style creator, Jessica Knight
Hairstylist @ Hair Metal Salon in Brooklyn, NY


How would you describe this look?

I took a classic yet ageless bob and texturized it throughout. I topped it off by clipper cutting the bangs, which I love doing!

My favorite part about this look is the drastic color. I love bold cuts with platinums, vibrant reds, and blue blacks.

Any advice for someone considering it?

When considering going to a lighter blonde, ask yourself:

1. Do I have preexisting color?

2. How is the condition of my hair?

3. What am I willing to spend?

4. Am I willing to keep up with this color every six weeks?

When considering going short or having bangs, ask yourself:

1. Am I willing to lose length?

2. Am I willing to keep up with bang trims?

A bob can easily transition into another beautiful haircut and looks great at any age. By adding texture, it gives off a more fun and versatile look.

I styled with a light matte texturizing paste by Fatboy, or you can use Davines Texturizing Spray. This cut is okay for any hair type, some types just may have to put more effort into styling. If the hair is coarse, weight may need to be taken out as well. For this look specifically, fine to thick straight or wavy hair works best.

This look is best suited for someone who doesn’t mind putting time into their hair and wants to make a bold statement.

Timeless Faux Bob

Timeless Faux Bob hairstyle
Instagram @lanielaneee

Q&A with style creator, Melanie Lane Durham
Hair & Makeup Artist / Salon Manager @ Prodigy Hairdressing in Petaluma, CA


How would you describe this look?

This is a roaring 20s-inspired faux bob. What you might not guess by looking at this style is that my model’s hair was actually waist length! My favorite thing about this style is how timeless it is.

Any advice for someone considering it?

My advice to a client considering this look is not to be afraid of bobby pins or hairspray! You couldn’t possibly have enough of either to keep the faux bob rolled up into place.

Hollywood Glamour

Hollywood Glamour hairstyle
Instagram @dollylockssalon

Q&A with style creator, Chelle Pillucere
Stylist / Fashion Maven @ Dollylocks Organic Salon in Saint Petersburg, FL


How would you describe this look?

My client was going to a black tie event and I thought Hollywood glamour would be great for it. My focus is classic hair design for my clients and I feel the hairstyle is the most important part of the look.

Any advice for someone considering it?

When going to an event like this, the hairstyle dominates the look. I made sure my guest arrived with clean hair with no product in it, then I created the foundation with Balmain Volumizing Texture Spray. I curled the hair in horizontal sections and set the curls with pins. I let the curls cool for a solid 20 minutes, then brushed the hair into the waves and pinned the back up. I finished the look with Balmain Strong Hold Hairspray.

Dramatic Finger Wave

Dramatic Finger Wave hairstyle
Instagram @jennababani

Q&A with style creator, Jenna Babani
Independent Hairstylist & Makeup Artist @ Salon Tribeca in Rancho Cucamonga, CA


How would you describe this look?

I created this roaring 20s-inspired look for my client’s special event. It’s definitely more of a dramatic play off of a traditional finger wave. We decided to pin it up and create more of an upstyle with it so that she could dance and move around freely without having to fuss over her hair.

My favorite thing about it would be the feminine quality it has overall. I especially love the waves framing her face!

Any advice for someone considering it?

This style is requested often, however it is not meant for everyone’s hair. Hair texture, length, and cut specifically go a long way in creating a design that will hold best for each individual client. For this style specifically, she had very long, very straight hair, but she did have a lot of layering which helped hold the shape without being too heavy on top. Her length did play a role in pinning it up because we wanted the lasting power throughout the evening.

This look would be excellent for photo shoots or special events for a dramatic and glamorous touch!

Elegance & Luxury

Elegance & Luxury hairstyle
Instagram @sofyramos

Q&A with style creator, Sofia Ramos de Vides
Hairstylist @ Salon Estilos in Guatemala City, Guatemala


How would you describe this look?

When I think of this 20s hairstyle, I think of elegance and luxury. Is a style that any girl can use for a wedding or a party, and it’s a look that has been featured on many red carpets and runways.

My favorite thing about it is exactly that! It’s a hairstyle where you can look elegant and sexy at the same time.

Any advice for someone considering it?

It is important to blow dry the hair first to give it some volume and to smooth it out. It is also vital to apply a hair product that will help mold the hair and give it durability. If the hair is too thin, I use the Full Volume line from Living Proof.

I use the shampoo, and I also like to use Full Dry Volume Blast hairspray on the roots of the hair. When the hair is ready, I use Flex Shaping hairspray (also from Living Proof) along with a curling iron to create the curls. The smaller the curler, the better the waves come out! I roll and pin each curl, leaving them pinned until the hair is cool. Once cool, I put the hair down and comb it.

Glamorous Finger Waves

Glamorous Finger Waves hairstyle
Instagram @publichairhouse

Q&A with style creator, Mel Mattison
Independent Hairstylist @ Public Hair House in San Diego, CA


How would you describe this look and what is your favorite thing about it?

Finger waves are a glamorous and timeless sculpted look that shines different lights on color. This is a gentle way to style hair, requiring low heat and some patience for a dry finish.

I love the art that it becomes as it dries and appreciate the smooth shine that happens both wet and dry.

What tips or products do you recommend to recreate this look?

This look requires help from your guest, as there is pushing of the hair against the scalp involved. Short hair is easier to maneuver, but most importantly, staying fluid through the sculpting is what makes this come together best.

Wet hair and a lightweight gel were used here. Utilize the fine tooth side of a comb for best results.

What type of client would you recommend this look for?

I recommend this look for anyone who would love to see themselves in a glamorous light. It’s especially great for guests who don’t want hair in their face. Truly, with a little makeup and lashes, finger waves really elevate an overall look. I feel extra beautiful when my hair is arranged like this!

Soft Finger Wave

Soft Finger Wave hairstyle
Instagram @jenmchair

Q&A with style creator, Jen Kohlenberger
Hairstylist @ JMc Hair Studio in Tustin, CA


How would you describe this look and what is your favorite thing about it?

I would describe this look as a soft yet structured finger wave.

My favorite thing about this specific look is that it’s not your everyday wedding style, but this bride owned it. As a style in general, I love that it’s a classic look that can be given a modern twist and will last all day and night.

What tips or products do you recommend to recreate this look?

Whenever I want to be able to comb through curls to manipulate them and keep them soft without losing their integrity, I use Kenra Thermal Styling Spray 19. To make sure the waves stay consistent and form together for the finished look, take small horizontal sections, spray Kenra Thermal Styling Spray from roots to ends on each section, comb through, wrap on the iron, and clip to cool.

When you remove the clip, comb through again and reform with your fingers. It’s a tedious process, but the end result is worth it!

What type of client would you recommend this look for?

I have found that this look works best on coarse hair. It tends to hold the shape well and can be manipulated easily to take on the wave structure that you desire.

This look is classic and can really be worn by anyone for a special occasion or just for fun.

Classic Retro Updo

Q&A with style creator, Danielle Ireland
Hairstylist @ Do or Dye in Robinson, IL


How would you describe this look and what is your favorite thing about it?

I would describe this look as a classic retro updo with the added fun of the victory rolls to make it stand out a bit more.

My favorite thing about this style would have to be the waves. I’ve always been a sucker for a vintage wave!

What tips or products do you recommend to recreate this look?

There are really just a few tips that I think are most important for this style. First of all, I always curl all curls in the same direction and pin to really set the curl so that it’s easier to manipulate later. A great product to help with this is a soft working hairspray like AG Aerodynamics. Spray as curls are setting and they will retain their curl memory as you brush them out without being sticky.

Lastly, backcomb the underside of the curls to bring them together and stay where you want them as you create your waves!

What type of client would you recommend this look for?

I think this hairstyle can work on any client! You can adjust the length of the bob, add more volume, or take away the victory rolls for a less dramatic look. It is completely customizable.

Long haired ladies have no fear, my client had hair halfway down her back! Just roll up the underneath, pin it in place, and it becomes the perfect cushion to secure your waves!

This look is perfect for any woman willing to rock it.

1920 Inspired Faux Bob

It’s no secret that women in the 1920s rocked cropped ‘dos — it was monumental that they did so! If your hair is long and you’re craving the bobbed look, though, fear not. Hairstylist Darian from Toni and Guy shows you how to create a faux bob, complete with finger waves, in this video tutorial. Darian does an excellent job of breaking this hairstyle down into easy-to-understand steps.

Finger Waves on Dry Hair

YouTube user MakeupWearables teaches another method for recreating those classic, 1920s finger waves. This one still requires some time and patience, but definitely not as much as the traditional finger wave method. Additionally, you’ll be left with soft and touchable hair instead of helmet head (a common side effect of 1920s glam). This method works best for medium to long hair.

Gibson Tuck Hairstyle

The Gibson girl and flapper coexisted in the ’20s, but the two had differing approaches toward beauty and fashion. While flappers opted to bare more skin and rock cropped ‘dos, Gibson girls took a more refined and conservative approach to their aesthetic. As a rule, they showed less than 10% of their bodies and tended to keep their hair quite long. Speaking of hair, it was often plopped, tucked and pinned in a very romantic manner. This Gibson Tuck hair tutorial, provided by Victoria Stanell over at BeautyLish, is a modern approach to Gibson hairstyles and is super easy to recreate.

roaring 20s hairstyles

Glam, Modern-Day Pin Curls

Fashion and beauty blogger Chriselle was asked what her three favorite hairstyles of all time were. The first one that came to mind? “Glam Curls,” she says, because the “perfectly polished curls are not only timeless, but also a modern take on the 1920s flapper finger waved hair.” To create this updated version of the 1920s girl, Chriselle employed a little trick that includes wrapping warm hair around her fingers to form a pin curl.

roaring 20s hair pin curls