40 Side Ponytails That You Will Love

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: Topsy-Tail Low Pony

Go back to your childhood roots with a hairstyle from yesteryear. Try out the classic topsy-tail pony and let it hang to the side. It may be an oldie, but it’s still a goodie!

#2: Wrapped High Ponytail

Side ponytail hairstyles just got a whole lot sleeker! For a night out on the town, try a side pony stacked high on your head and wrapped at the base. Add a little gel before you brush it up to make sure you won’t get any wispy hairs or strays.

#3: Fancy Updo with a Side Pony

Side ponies aren’t just for casual attire! Get a little complex and create with three topsy-tail ponies on top of each other along the side of your head. Secure the bottom of the pony with an elastic band and curl the tips. Voila! Now you’re ready for any formal event.

#4: Cascading Braided Pony

Go medieval on your hair and pair a braided side pony with luscious, lovely curls. Secure the braid just behind your ear and only tie about ¾ of the hair length with an elastic band. Allow the pony and the rest of the loose hair to cascade down the side of your neck for an ultra-romantic ‘do.

#5: Criss-Cross Side Pony

Take a break from your typical side ponytail and add some criss-cross action to the mix. Simply overlap sections of hair and pin them (so the bobby pins don’t show) until you hit the base of the neck. Tie the pony and you’re good to go!

#6: Twisted Retro Ponytail Updo

Channel your inner ’60s diva with a beautiful bouffant ponytail. Tease the hair at the crown and backcomb it so it’s voluminous and full on top. You can pin a couple of curls to the back of the head to add some pretty detail to your look!

#7: Beach-Friendly Braided Pony

Make waves for your next beach day. Perfect for frolicking around in the water, a plaited side pony looks great and keeps everything in place while you go about your business. It’s also super easy to put together!

#8: Pretty Plaited Pony

Get a side ponytail that’s tres chic and tres easy! All you have to do is to tie your hair to the side and wrap it at the base. Then, grab a section from within your pony and braid it loosely. Spritz the braid with hairspray and allow it to hang loose.

#9: Messy Side Pony

Messy, undone looks are very in right now. First the messy bun, then the messy beach waves and now the messy pony! The key to achieving this look lies in the products used. Make sure you invest in a quality texturizing spray or powder and maybe a styling paste to make your hair piecey and not too perfect.

#10: Romantic Ponytail

Dial up the romance with your hair! Perfect for a wedding or formal affair, a feminine twisted side pony is a great go-to updo. For extra pretty points, add some hair accessories like flower clips or a bedazzled comb to help show off your look.

#11: Beautifully Braided Ponytail

Some side ponytail hairstyles are princess-worthy … Disney princess, that is. Channel your inner Elsa (from Disney’s Frozen) and try out a lush braided ‘do that wraps around the back of your head and continues down the shoulder.

#12: Perfectly Imperfect Side Pony

When in doubt, go for something old and faithful. A basic low side pony is ideal for those days when your hair just doesn’t want to behave or you’re short on time. This style takes a minute or two and still delivers a polished look.

#13: Pony and Dutch Braid Combo

These days, braids and ponytails go together like peanut butter and jelly. Keep that magical partnership going strong with a thick, full Dutch braid that wraps around the side of the head and ends with a curled pony. Make sure to tug at the braid to make it fuller and messier looking!

#14: Pumped-Up Side Pony

Give your side ponytail some pizazz by wearing it nice and high. Backcomb the crown for a bouffant. Pull the hair up and secure just to the side of the crown. Leave the two wide front sections of your hair loose and pin them under the pony. The result is a sleek and voluminous updo that’s a unique take on the classic pony.

#15: Loosey Goosey Ponytail

Sometimes you just have to let your ponytail hang free! After braiding your hair low, messily and loose along the nape, bobby pin the braid behind the ear and allow the hair to hang freely and fall onto your shoulder.

#16: Tangled and Twisted Ponytail

Messy hair is great hair! Show unruly curls who’s boss by throwing them into a soft side pony. This immediately makes your hair manageable and looks polished and elegant.

#17: 2-Minute Side Pony

Long hair is beautiful but can sometimes be difficult to style and manage. That’s why the side ponytail is a popular option for those with long locks as it allows one to take back control and do it with style and flair … especially when you throw a braid into the mix.

#18: Faux Hawk Ponytail

Go a little bit rock ‘n’ roll with your side pony by creating a cool faux hawk. Style a Dutch braid down the middle of the head and pull at its parts so it transforms into a mohawk-like shape. Now all you need is a guitar and some backup singers!

#19: Braided Crown Pony

A braid and pony is a great way to show off your hair color and highlights. The plaited pattern showcases the dimension in your hair beautifully. So, if you just got your hair colored, throw it into a braided side pony and prepare for some compliments!

#20: Fabulous Fishtail Side Pony

Dutch braids are often an obvious option for the braided crown and side ponytail. But don’t underestimate the power of the intricate fishtail. The smaller pieces create an interesting pattern and look more complex. So try a fishtail on your next pony and see if you don’t become a fan!

#21: 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.

#22: 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!

#23: 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.

#24: 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.

#25: 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.

#26: 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.

Instagram/ @sunkissedandmadeup

#27: 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.

#28: 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.

#29: 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.

#30: 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.

#31: 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.

#32: 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.

#33: 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.

#34: 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.

#35: 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.

#36: 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.

#37: 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.

#38: 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.

#39: 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.

#40: 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.

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!