Messy Side Ponytail

My lovelies, you know the messy side ponytail from J. Crew’s spring lookbook? Well, I really wanted to learn how to do it myself, so I invited over my friend Caroline (who is a hair genius) to explain how to get the look, and the fabulous Jamie Beck took a few photographs. (What I love love love about this style is how the top looks like a beehive!)

Here are Caroline’s steps, if you’d like to try it out….
1. Start with day-old hair…meaning it’s been a day since you’ve washed it. (If you must wash your hair, then use a volumizing spray to add oomf; and if your hair is oily, use a French dry shampoo to build body and texture.) Now make a deep side part on one side of your hair. You can use a rat-tail comb to get an extra straight part.

2. Backcomb the top quarter of your hair. Basically, brush the hair downwards toward your scalp so it’s sort of frizzy and can stand on its own.

3. Gently brush the very top layer of your hair to make it smooth on the top. That way, all the backcombing will be hidden under the layer that you brushed. Still, don’t brush too much, you want it a little messy.

4. Take the entire backcombed section and pin it behind your head. To make it secure, place the bobby pins in an “X.”

5. Now take all your hair and put it in a low ponytail at the nape of your neck. Tighten the rubber band as tight as you can. This will help “push” your hair up, creating more volume at the top.

5. You can either leave the rubber band exposed, or hide it by taking a small half-inch section of hair from the ponytail and wrapping it around the rubber band. Take a small bobby pin and pin the hair to the rubber band.

6. Rough up the ponytail with your fingers to match the texture at the top of your hair. Use the same motion as you did to back comb, but use your fingers instead, since this will create a messy texture but will be softer and gentler than using a comb. Remember, this look isn’t about perfection; it looks best slightly messy.

Let’s do it! Thank you so much, Jamie and Caroline! xoxo

(Photos by the wonderful Jamie Beck.)

  1. Gray says...

    I know I’m late to the game, but this was life changing. I’ve been trying to do this for years and have even asked my stylist to show me how. Thank you maam…

  2. This is absolutely STUNNING♡♡♡

  3. Hiiii… i love it!
    Congratulations os Brazil!
    Have a nice day!!!

  4. Tricia says...

    Any suggestions for girls with thicker hair? Bobby pins are basically useless in my hair…

  5. Love your ombre color – it’s perfect!!

  6. Anonymous says...

    i love this! my hair is so slippery and thin i thought this wouldn’t work, but it does! and beautifully too i might add.. gotta try out the other ones too! :- )

    Jonna, Finland

  7. Anonymous says...

    i love the style. but did you photoshop her arms in that last one? ewwie.

  8. Bertrand says...

    I suppose one and all should browse on it.
    Cucumbers recipes

  9. Love this hairstyle. I would love to share on my blog.

  10. This is my favorite look! Will try to make it tomorrow.

  11. Annie says...

    You mean you don’t just put your hair in a ponytail with a rubberband on the side? Who knew? LOL I am so naive!

  12. oh my gosh! This is soooo cute specially for the summer.

  13. Love this, it’s so fabulous. Can’t wait to share, thanks! {}

  14. I noticed you said: the lipstick is a combo of surprisingly cheap drugstore brands. cover girl lipstain in plum with revlon super lustrous in kiss me coral, but there’s two cover girl plums, could you please tell me which one?
    Thank you
    Beautiful girl, beautiful style, I’ll have to see if I can do it on my hair though :/

  15. Oh so beautiful!Im going to attempt to do this today!

  16. It’s rattling nice article. Thanks for conversation about it as I am curious in this subject.r

  17. Hi Jo, thank you so much for sharing all the steps!
    I would try ;)
    Your blog is great,
    kisses from Italy,
    It would be lovely to have you on my blog, I’ve already added you!

  18. Love this style! I really like the look of messy hair (meaning supposed-to-be- messy not lazy-gross-messy) but I am sometimes too insecure to pull it off afraid that people might think I just rolled out of bed….

    Anyways, great post!

  19. I’m going to Maui in a couple of weeks. This is the perfect effortless chic hairstyle with your maxi dress thrown over a swimsuit. Thanks for the inspiration!

    <3 Sophie Michele <3

  20. Anonymous says...

    to anon 9:07 wondering about the wallpaper. I don’t know if they make wallpaper or not but I have a Dwell duvet in this same pattern and colour so perhaps it is just a sheet used as a backdrop or else they now sell the same pattern as wallpaper. I would contact Dwell to find out.

  21. LOVE this! Thank you :)

  22. i just have to say, i have been doing this look like every other day. i am obsessed. beautiful model! great tutorial!

  23. I luv this look so I’m going to give it a try!

  24. I love this messy, yet chic look! As well as the ombre style hair… very cute!

  25. Love this look and just did it today. and blogged it ;)

  26. love this!! thanks for the step by step! I have an appointment later today and just tried this. It doesnt look exactly the same but I’m happy with it :-)

  27. rocking this look today, but with my own little side plait take on it. xo

  28. So fun! Just did it and off to work I go with something fun and funky instead of ‘up-in-a-bun’ because I awoke too late to wash it this morning! Thanks!

  29. love it!! looks like Caroline cut her hair much shorter – looks great!

  30. i’ve been seeing this do on all the girls at the private school across the street from my house. at first i thought they were too lazy to brush their hair– now i know it’s a look!

    i did have to laugh, though. this reminds me of a girl who was in one of my classes in college. she would sit there all through the entire class, gently touching and moving tiny strands and locks of hair to ensure that it was still “messy.”

    effortless? not quite. cute? i think so.

  31. ooh! This beautiful~

    I hope you don’t mind me sharing this on my blog >.<

  32. Thank you so much for posting this! I am OBSESSING over the J Crew spring catalog. Messy hair, hot red lips… It’s to die for.

  33. I love how you did this- enough pictures- and a really good- description. I am totally going to try it. I have a client that does this to perfection and have been wanting to ask her.

    Now I will try it – ( on a day we dont meet: :-)
    Thanks Jo! x

  34. Anonymous says...

    Apart from the amazing ponytail, it also seems that Caroline has amazing tatoos. Can’t seem to zoom in close enough to see what they are?

  35. Anonymous says...

    oh, and her tights too?

  36. Anonymous says...

    Great post! Any chance we can know where her tank is from?

  37. Thanks for this, I even tried it yesterday for work it was wonderful!! Got my hair out of my face but still looked cute.
    I also looked up the bun look which is similar to one I use already (albeit with an elastic band) but much more elegant.

  38. It’s still an experiment, I think my hair has to grow some more!
    (btw you’re pinned a lot on Pinterest)

  39. Thank you for posting this. Great tips!

  40. I am going to be a bridesmaid this spring and I do declare that this will be my hairstyle. So pretty.

  41. Vanessa says...

    Amy Winehouse has been doing this look for years.

  42. I love that hairstyle. Trying this next week! Thanks!

  43. thanks emily. while it’s always easy to jump to conclusions based on an image, i can assure everyone that i am just as healthy as the next person. yes, i am skinny. no, that doesn’t mean that i need a sandwich or that you should feel bad for me. people often forget that just because you are naturally thin doesn’t mean you are anorexic- i used to be afraid to get up to go to the bathroom during meals because i didn’t want everyone at the table to think i was throwing up…all because i was thin and couldn’t do anything about it.

    for those who asked- the lipstick is a combo of surprisingly cheap drugstore brands. cover girl lipstain in plum with revlon super lustrous in kiss me coral.
    eyeliner is lorac front of the line liquid in black
    blush is tarte cheek stain in flush
    and mascara is tarte lash hugger in black (eco friendly and no parabens!)

  44. I tried this look yesterday and had so much fun wearing it out! I’ve been parting my long hair down the middle for months now–it was so fun to do a dramatic side part. Thanks for sharing this!

  45. I love this! …what’s that lipstick? It’s great.

    It makes me sad to see people commenting on caroline’s weight. This is a place where women of all shapes and sizes and colors can look at beautiful inspiring things together. No need to hate! I’m thin and eat all of the time. I keep myself healthy and people always say I’m so thin. But, it’s who I am. I wish people would realize that commenting on someone’s weight–whether thin or heavy–is a very personal thing. Respect.

  46. evet çok şık olmus beğendim ama saçlarım kısa olduğu için deneyemiycem.sevgiler

  47. I wore my hair like this today. Soooo pretty! Thanks for the tip.

  48. Anonymous says...

    Gorg photos! I’d also love to know what lipstick your model’s wearing. It’s a perfect shade!

  49. I love this. It’s messy yet completely glamorous and feminine.

  50. oh my gosh she is so cute!! she is so cute! her hair is amazing. i love the ombre hair. gosh. i just love this.

  51. I tried this as soon as I read it yesterday morning and got compliments on it all day, even if it didn’t look quite as bomb as yours did!

  52. That side ponytail looks great! Thanks so much for the tutorial.


  53. You look kind of alike, as good friends often do.

  54. my husband is trying to do this for me. he’s so cute!!

  55. I felt like I was stalking a girl at the Gap yesterday I was dying to ask her if she was wearing a bump-it in her beehive inspired ponytail, it was that good!! I tweeted you a little love back, thank you for a great post.

  56. Oh I love this!!! I am just not too sure if I could actually replicate this…. I barely master straightening my hair, and every time I try to use a curling iron there is a 90% chance I burn myself…
    I shall try it!

  57. I just had a conversation about a messy ponytail with a friend the other day about an event I was going to.

    her: how are you wearing your hair?
    me: I’m doing a messy pony.
    her: that sounds like a sex position.

  58. I need to study this religiously! It took me years to grow out my hair and now I can’t do anything with it.

  59. Lauren says...

    Joanna- Would it be possible to get Caroline’s make-up tutorial? Her makeup looks beautiful in these pictures!

  60. Your friend looks so nice and natural. Love those pictures.


  61. Is there something wrong with me? I absolutely cannot stand this look! Love your blog in general, but this hairstyle? Eww.

  62. She is gorgeous, love her ponytail.

  63. Tried it – LOVE it. Thanks

  64. I just adore this – am thinking of wearing it as my bridesmaid hairstyle for my sister’s wedding next month! Thanks so much!

  65. love this!! i’m doing it right away!