What are your associations with side ponytail hairstyles? Well, we all look back fondly on the ‘80s as an iconic time with a rebellious flair in fashion and hairdos. Close your eyes and imagine an ‘80s prom queen; chances are, you see bright blue eye shadow and a high side ponytail, backcombed and hairsprayed to perfection.
Effortlessly Chic Side Ponytail Hairstyles
If all those John Hughes movies taught us anything, it’s that we can’t all be Molly Ringwald, but that doesn’t mean we can’t mimic the hairstyles of her prime with our own twists and tricks. So if you want to be a current day ‘80s princess, here are some modern takes on the side ponytail that are totally fresh and perfectly updated.
#1: Messy Blonde Ponytail with Faux Pompadour
Arguably one of the easiest and appealing hairstyles is a ponytail. This one may seem a little odd at first, but there is something incredibly stylish about rocking a messy hairstyle, especially if it’s a ponytail. The side ponytail updo definitely speaks a messy flair although the ponytail itself is so delicately teased that it looks rather sleek and wispy. The twisted faux pompadour in the front adds to the messy (or bed-head) look of this fuss-free ponytail.
#2: Fishtail Braid Ponytail
In the past few years fishtail braids have been seen everywhere from runways and fashion editorials to red carpets and stylish women around town. So what is a better way to give this hairstyle a boost than to turn it on its side…literally. This ponytail gathered to the side and punctuated by a fishtail braid is the best of both worlds, and it looks incredibly chic!
#3: Wavy Free-Flowing Messy Ponytail
Besides having envy-worthy hair that looks like you just stepped out of the salon, one of the best things about a great hairstyle is that it’s easy to achieve. Sure, expertly sculpted and coiffed hair looks amazing, but for the average woman who doesn’t have the skill set or the time to complete it, simple and stylish-looking ‘dos are essential. This effortless blonde ponytail features twisted sides and backcombed tresses that help to form the ponytail with a feminine look – and that’s easy to achieve.
#4: Intricate And Messy Ponytail
When you take the styling techniques from both messy and intricate hairstyles, and combine them styling your side ponytail, the result can be unexpectedly cool. Check this half up fishtailed pony. The long, exaggerated wisps of hair that are escaping along the side and the back add to the messy look. However, the intricacy of the fishtail braid that’s thrown to one side is what really creates the lasting impression.
#5: Long Classic Ponytail
What makes a ponytail so fun and personal is that you can create practically any variation you like, in this case it happens to be the side ponytail. This ponytail resting on one shoulder is classic, understated and universally flattering. Long, sleek, brunette strands are formed into a chic style that features no extra frills except the braided section that is wrapped around the ponytail.
#6: Twisted And Pinned Blonde Ponytail
Certain ponytails require more skill and commitment than others, and this side version is a perfect example. Everything from teasing, twisting and pinning to curling and back-combing is utilized in this detailed and drama-filled style that is definitely worth all of the styling time required to achieve it.
#7: Braided Crown Ponytail for Round Faces
Did you know your face shape has a great deal to do with the type of ponytail you should wear, even when it comes to side ponies? For those of you who have round faces, a messy side ponytail that features a high braided crown adds length to your face for the necessary balance.
#8: Wavy Side Ponytail with a Crown Braid
The element of surprise is one of the best techniques utilized in the hairstyle world, meaning that your hairstyle can appear simple from one side and then offer a surprise from a different angle. That is what this flirty hairstyle does, as one side is sleek and slightly waved at the ends, while the other side presents a braided half crown.
#9: Simple Messy Side Ponytail
When you have long hair, a ponytail is literally your best friend, as it allows you a quick style option and also a way to keep your locks out of your face. This pony is simply styled low and off to the side with messy ends.
#10: Sculpted And Constructed Black Ponytail
Not all side ponytail hairstyles are quick and effortless, some are so beautifully sculpted and constructed that you’ll be amazed. Featuring super long strands that are brought up high and to the side, this ponytail also includes the braided base and a very cute design of baby hair along the hairline to punctuate this black ponytail.
#11: Braided Maze Low Ponytail
What some may not realize is that braiding hair is a very tough skill, but when done properly it produces absolutely stunning results, just like the pony seen here. Braids are placed throughout this style to create some sort of ponytail with a braided maze that is equally fascinating and guaranteed to turn heads.
#12: Naturally Curly Ponytail
African American natural hair can be styled in different ways, including a cute ponytail. Here, the naturally curly texture is embraced to create a voluminous side pony. If your natural hair is not of this curly texture, you could use flexirods or do a twist-out overnight to achieve some lovely curls.
#13: Twisted Front Curly Side Ponytail
Hey, there is nothing wrong with adding some hair extensions to come up with the hairstyle of your dreams. This side ponytail creation incorporates extensions to achieve the desired length and volume for the lovely ponytail with soft waves and a twisted front.
#14: Wavy Ponytail with Flower
Deciding to add hair accessories to your side pony is a lively way to personalize your look with a dash of feminine flair. Here we have a wavy style that is accented with a pretty, deep side part and finished with a bright flower placed at the base.
#15: Black Curly Ponytail with Headband Braid
Textured hair makes for a naturally great ponytail because you don’t have to worry about adding extra curl or depth. This textured side pony also features a chunky braid along the hairline that runs behind the ear to create the necessary height for the pretty, finished look.
#16: Fishtail Ponytail with Hair Extensions
Sometimes you come across a ponytail so perfect that you know there is no way it could be real. Well, these days it’s probably not. As seen with this flawless side ponytail hairstyle, (which is a full ponytail piece that has been fishtail braided) all you have to do is simply to attach it invisibly to your real hair and go.
#17: Sleek Ladylike Ponytail
Ponies are extremely flirty and girly, which means that pairing this hairstyle with a contrasting fashion choice works wonders. Modest ponytails perfect for the office, however, can be a tricky decision. Still there are some that fit the bill so well that you won’t have a moment to hesitate whether to style them or not on a busy morning. Simple, sleek and chic are the best words to describe this ladylike side pony that can easily take you from the office to cocktails with your co-workers.
#18: Blonde Braided and Twisted Ponytail
You should never be all twisted up…unless it’s your ponytail that’s doing the twisting. This twisty pony is ideal for weekend fun or when you want to spice up an understated outfit. For a dose of added flair, you could also place a flower at the base.
#19: Long Ponytail with Side Braid
One really long, well-placed braid can go a long way to amp up your basic side ponytail. By starting the braid at the very top and bringing it all the way down and to the side, you will create a ponytail that really stands out from the crowd.
#20: Wavy Ponytail with Side Bangs
A deep side part is uber dramatic, and it’s the ideal way to make your ponytail appropriate for evening activities. This pony would look great with an elegant evening gown or cocktail dress because it’s a formal type with a fancy touch. Complete the look with perfectly curled ends and flipped bangs.
#21: Naturally Messy Pony With A Centre Part
Side ponytails are one of the easiest styles to recreate at home. All you need is a hair elastic and some inspiration. If you want a messy style that gives off a relaxed, natural vibe without going over the top, leave the front pieces of your hair out and focus the ponytail lower towards the nape.
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#22: Wavy Side Ponytail Hairstyle
For something a little different, follow in the footsteps of this Sexting in Suburbia seductress. Kelli Goss keeps it elegant and classy on the red carpet with a curled side ponytail. To get this style at home, all you need is a curling wand and a few bobby pins. Curl the ends of your hair, wrapping the hair around the wand in different directions to avoid uniformity, and pin it back while keeping the front mildly loose.
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#23: Pony With An Edgy Face-Framing
In this photo, Nicole Beharie rocks a new take on the modest style at an Entertainment Weekly party. By keeping the front pieces out of her low ponytail, she gets a nice face-framing effect that makes her face appear slimmer. If you have chubby cheeks that everyone likes to pinch, this style will minimize your problem.
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#24: Centre-Parted Messy Side Ponytail
You might know her from American Horror Story or The Newsroom. Grace Gummer expertly shows off a calm and collected vibe with this carefully styled side ponytail. Perfect for a more formal occasion, you can try this look at home paired with your favorite little black dress. Don’t forget to leave a few strands out in the front, so everyone knows you’re totally not trying that hard.
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#25: Paired To Perfection
The best part of this look is the way Penny Johnson pairs her simple hairstyle with an eccentric dress. When you keep your hair minimally styled, it leaves ample room for your outfit to shine. If you have a new dress you want to show off, pull your hair into a side ponytail and flaunt it, girl!
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#26: Slicked Back Side Ponytail Style
If you want to look brooding and mysterious (or just adorably enigmatic like Ali Landry,) breathe some new life into your side ponytail by slicking your hair back with either hairspray or gel. Warning: Do not pick up any old gel at the drugstore. Invest in something a little nicer or you might wind up looking like your hair is made of plastic.
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#27: Venerable Volume
Kristen Stewart is known for her low maintenance attitude towards beauty and style, but that doesn’t stop the Twilight star from cleaning up well on special occasions. Her voluminous take on the side ponytail can be achieved with careful backcombing before you pull the rest of your hair back. If you wait until after you already create the ponytail, you’re risking major frizz.
Jaguar PS / Shutterstock.com
#28: Side Ponytail Hairstyle With Loose Layers
Sandra Taylor kills it with this hairstyle. Her side ponytail has legendary volume, and the side swept bangs are a perfect touch to add. For all you ladies out there with layered hair and bangs, this one’s for you. Sweep your fringe to the side of your face and then use a curling wand and some sea salt spray to create messy waves within the ponytail. To get rid of the perfect spirals and create nice volume instead, just tousle your curls and backcomb – your hair is getting bigger and better!
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#29: Cute Pony With A Mini-Braid
Some people might consider ponytails to be boring. Ali Dee disputes that argument by adding a few personal touches to this look—soft waves and a mini-braid to make it her own. This is the kind of look you can wear in the warm weather without having to worry about humidity or sweat ruining a style you’ve worked hard on. Try it out at the beach or a music festival!
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#30: Casual Side Ponytail Hairstyle
Check out this gorgeous side ponytail on True Bloodstar Amelia Rose Blaire. This is as simple as it gets, but paired with the right outfit it can be a fabulous transition into classy formalwear for a night on the town. Try a dress and some glowing red lipstick with this ‘do. You’ll be the life of the dinner party!
Helga Esteb / Shutterstock.com
#31: Modern Beehive
Kelly Osbourne wowed the world with her transformation from a moody and dark teenage reality star into a genuine fashionista. Since she started on Fashion Police, her purple hair has been an unstoppable force of nature. Kelly makes the side ponytail all her own with a modern beehive for added volume. Sprinkle some light hairspray to keep it in place if you try it at home.
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#32: A New Take On A Side Ponytail
What does it look like when you combine a side ponytail with a half up half down style? The answer lies in this photo of Betsy Brandt. To recreate this look, take the two front sections of your hair and pin them together at the nape of your neck. Then take the rest of your hair and tie it into a side ponytail. Voila—a new take on the old classic look!
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#33: Pulling It Back
Sadie Calvano’s side ponytail is created with perfectly crafted ringlets and it’s actually pretty easy to pull off. Pull all your hair back and slightly to the side into a high ponytail. Then, use a curling iron, holding it in place for a moment longer than you usually would to ensure the style holds. Hairspray is a necessity, and don’t even think about brushing or the ringlets will fall out!
Helga Esteb / Shutterstock.com
#34: Side Ponytail With Side Bangs
How chic is this all-side hairstyle from Meredith Monroe? She styles it all to the right—the ponytail and the bangs, creating a casual look that you could wear out on a date or in a professional environment depending on how you’re feeling. If you add a few pieces of minimalistic jewelry to this hairstyle plus a button-up top and a pencil skirt, you’re ready for work!
Helga Esteb / Shutterstock.com
#35: Over The Top
Never be afraid to take beauty dares or to try something new and unexpected! Kimberly Cole shows us that she can do no wrong by putting her side ponytail right on top of her head with an oversized wrap around the pony base. If your hair is long enough to fall gracefully over your shoulders with this ‘do, try it out; you’ll be surprised how much you like it!
Joe Seer / Shutterstock.com
#36: Side Ponytail With A Silvery Scrunchie
Adding a hair accessory is a perfect way to spice up what might otherwise be a bland side ponytail. Take Pauley Perrette for example. Her ponytail is a simple take on the quintessential style, but she manages to stand out from the crowd of boring-haired beauties by adding the silver scrunchie. It’s like a cherry on the top of a sundae!
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#37: Short & Sweet Pony
Don’t assume you need long hair to try out the side ponytail trend. Short hair works just as well! Take a look at Mara Brock Akil’s shorter tresses pulled back into a sophisticated side ponytail. Try it out for work or class; it’s versatile enough to go with any occasion.
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#38: Long Face-Framing Waves For A Side Ponytail
As we’ve seen in earlier photos, leaving the front pieces out of a ponytail can be a great way to shape rounder faces into looking slimmer. This works with banged beauties and non-layered ladies too. Stunning Rachel Fox frames her flawlessly made up face with long strands that fall down past her shoulders for a sophisticated style.
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#39: Braided Beauty
Side ponytails are possible with any type of hair—long or short, curly or straight. That’s one of the best reasons to wear it; there are no boundaries! Even if you have braided hair, you can pull it all back to create a new and unique hairstyle.
Helga Esteb / Shutterstock.com
#40: The “No Ponytail” Side Ponytail
Some side ponytails are loose enough that they stop looking like ponytails altogether, and that’s not necessarily a bad thing! To mimic Brianne McLaughlin’s lax style, pin your hair back and slightly to the side, but not too carefully. The more insecure the bobby pins are, the freer and more relaxed your hairstyle will be.
Helga Esteb / Shutterstock.com
So you’ve got an idea of a trendy side ponytail, and you have your options now. No matter where you’re headed or what you’ll be doing, a side ponytail is the right choice for your next occasion!
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