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  1. November 2, 2012

    […] Finally, a (comprehensive!) guide on how to roll your jeans […]

  2. November 2, 2012
    Alyssa says

    What a cute post concept! I’m a big fan of the 2-3 small rolls with flats and booties. And I’ve actually NEVER thought to roll my jeans and then tucking them into socks for high boots. Such a simple, good idea!

    The Glossy Life

  3. November 5, 2012
    Olivia says

    Who makes the black booties with leather bands and who makes the tall brown boots in the last image? This is a great post!

    1. October 7, 2016
      Heather says

      Carlos makes a bootie called the Hollie that looks a lot like that. There is a brown with brown straps and a black with black straps. I know Famous Footwear carries them, and were on sale last weekend. I know because I bought them in the brown color and am wearing them today with skinny jeans (still need to figure out the roll though).

  4. November 5, 2012

    I LOVE rolling my jeans!!! thanks for these tips!!! pinning this now! :)

    Sandy a la Mode

  5. November 5, 2012
    Jeanine says

    Please share who makes the wine suede booties. Adorable!

  6. November 7, 2012
    Ashley says

    Oh my gosh loving this post! I will definitely be using it as a reference. I can never decide if I should roll my jeans or not haha i regularly deal with big dilemmas in my life :)

    xo SideSmile,

    SideSmile Style

  7. November 9, 2012
    Kb says

    This is so useful thank you! I never wear jeans much as I’m slightly scared of the whole ankle situation!

  8. November 13, 2012

    Those pink heels are awesome!!! Thanks for the awesome tips, I’ve always wanted to know how to do this, properly!

  9. January 2, 2013
    maria says

    I love this, it answered all of my questions!!! thank you!

    1. November 21, 2013
      tim says

      can i borrow your hands to roll my jeans

  10. January 21, 2013
    Paige says

    I am obsessed with this post. I am always rolling my jeans but never know if I can truly pull it off. You have reassured me that I am on the right track!

  11. February 22, 2013
    Jenny says

    I’m a 55 year old fashion nut. ( Too old to be called a fashionista). I love to stay in style and change looks to keep updated all the time. I’m just gossiping I guess about how it can be tricky to dress age appropriate and still look and wear cute clothes. I am also small at 5’2″ and 108 lbs. Because of my size I find myself in the junior dept often. I buy the jeans and some tops but always make sure the correct LONG camisoles are worn so no stomach EVER shows. The boyfriend jeans are my favorite right now I just buy them with no distress like holes and tears. Dressing in style can be done and can be done well just AGE APPROPRIATE is the key. No one over 45 should be showing too much skin and certainly no abs. Another important thing to look good as you age is stay in shape and have your teeth whitened. I call whitening teeth “the poor girls face lift’ . White teeth make a world of difference along with updated hairstyles every year. So you twenty somethings dont get bummed out thinking your style life is over when you hit 40 or 50 its not. In fact its much nicer because in most cases you will have lots more cash to to spend. Just a 55 year old thinking out loud.

    1. December 24, 2014
      Sharon says

      Thank you so much for your encouraging words. I’m turning 50 soon, have lost 50 lbs his year, and while I’m not trying to re-invent my look, I am trying to branch out, get out of the Mom jeans and take better care of myself. I look online often for the do’s and don’ts and I like your practical advice. Thank You!

  12. April 2, 2013
    sarah says

    As someone who is 5ft2 (and even petite pants are to long on me) I have always cuffed my jeans, and I can tell you a lot of boyfriend jeans have ankles to wide to look like the picture when cuffed.

  13. April 11, 2013
    Tammy says

    What about wedges

  14. April 29, 2013

    magnificent points altogether, you just won a new
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  15. May 15, 2013
    Sarah says

    Great post, and I have those same boots in the last picture. Love them!

  16. June 14, 2013
    Emily says

    Love the post, where are your jeans from????? So cute!!!

  17. July 15, 2013

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  18. July 26, 2013

    […] found this cool article by, entitled How to Roll Your Jeans – this 80′s trend, together with boyfriend jeans, have been resurrected today. It […]

  19. August 4, 2013
    Shelby says

    How would you recommend to roll skinny jeans with converse tennis shoes? I’m just wondering…

  20. August 12, 2013

    naturally i seriously like your website together with
    tv thanks a ton for that guide

  21. September 3, 2013

    wow, great Tip thanks a lot!

  22. September 27, 2013

    […] Shoes are also a big factor here. If you carry your weight on your top half, you might want a chunkier shoe or boot to balance out the top and bottom of your silhouette. If you love ballet flats, try rolling the skinny jeans to create balance. This is a great article on how to properly roll your jeans. […]

  23. September 27, 2013

    […] The Proper Ways to Roll Your Jeans. […]

  24. October 3, 2013

    great post love it!

  25. October 10, 2013

    Very good tip!! We just tweeted this out :) Thank you!


  26. October 11, 2013
  27. October 19, 2013
    Morgan says

    Okay…this is kind of amazing!!! Thank god I stumbled upon your website here! I’m new to blogging so very happy I found you!

  28. October 20, 2013

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  29. October 23, 2013

    […] it comes to cuffing denim, there is an array of methods. Advice from a Twenty Something  has a great how-to, and tries her best to cover nearly every method. For those of you who like […]

  30. November 6, 2013

    […] boots can be found at Gap. Then, pair them with your favorite tank top and jeans. Don’t forget to cuff your jeans in order to show off your boots. Last but not least, add an infinity scarf in your […]

  31. November 21, 2013
    Audris Shelby says

    Wow. . awesome!I’ve found these rolls very helpful before I’ve had confusions how to roll right of course in a fashionable way!Thanks a lot for the infos!

  32. November 21, 2013

    Fun post! Thank you for sharing!

    SVICA Jeans
    “The Customizable Tuxedo Stripe Jean”

  33. December 12, 2013
    max says

    And with this post, I am officially in love with this site.
    Off to read EVERYTHING you’ve ever written!

  34. December 19, 2013
    Jessie says

    One little addition that I’m shocked didn’t make it onto this list…

    If your jeans are too loose around your ankles when you roll them (boyfried jeans, straight legs, or even some boot cut jeans), the secret is something any 80s/90s kid can do like a champ:

    TIGHT-ROLL those suckers!

    Especially if you’re just trying to make your jeans fit neatly into a pair of boots, tight-rolling can help everything fold up nicely so that you don’t have a balloon of denim sticking out of the top of your boots. This was a trick I learned from my dad, who was big into the grunge movement during his college days (’89-’93). If you don’t know how to tight-roll, search google or youtube, there are plenty of demos out there.

  35. January 7, 2014

    […] The Proper Ways to Roll Your Jeans. […]

  36. January 13, 2014

    […] with boot cut jeans, but I tried today. (By the way, here is a nice guide on how to roll them up: […]

  37. February 2, 2014

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  38. February 24, 2014

    Wonderful website you have here but I was curious if you knew of any discussion boards that cover the same topics talked about
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  39. February 24, 2014
    Linda says

    Keeping your jeans in your boots? Get jeangrabbers on Great $12.95 best ever

  40. February 27, 2014
    Kristen says

    I rarely comment, however i did a few searching and wound up here How to
    Roll Your Jeans. And I do have some questions for you if you tend not to
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  41. March 10, 2014
    Angie says

    This is perfect! I have been wondering how to roll my jeans depending on what shoes I am wearing, and this post just showed it all! It gave me all of the information I needed. I also have found another website that shows a couple of the same rolls in step-by-step detail, which I found helpful. Thought is post is great for seeing many kinds of rolls with different shoes! Great post!

    The other website is:

  42. April 13, 2014

    […] Now I only showed you all how to roll your jeans when wearing flats because all I wear are sandals; butttttt if you’re interested in how to roll your jeans with booties, heels, etc click here! […]

  43. April 25, 2014

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  44. May 3, 2014

    I never roll my jeans, but this post might have just encouraged me to give it a try!


  45. May 19, 2014
  46. May 24, 2014

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  47. May 25, 2014

    […] 3. How to roll your jeans depending on the shoes you’re wearing ( […]

  48. June 14, 2014

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  49. June 25, 2014

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  50. July 3, 2014

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  51. September 7, 2014

    […] Now I only showed you all how to roll your jeans when wearing flats because all I wear are sandals; butttttt if you’re interested in how to roll your jeans with booties, heels, etc click here! […]

  52. February 3, 2015
    erika says

    So I actually found a great way to put knee high boots on w\o socks. You just put your jeans on halfway and then pull the boots on & then pull jeans up! That way they’re nice & tight!!

  53. February 25, 2015

    […] the knee. Save your boyfriend jeans for ankle booties and make sure to roll them a few times using this handy-dandy guide […]

  54. February 25, 2015

    […] by all the questions I got about how I tied it. Just like the way you tuck in your shirt or roll your jeans, the way you tie your scarf can make all the difference in your outfit. So if you’re […]

  55. March 10, 2015

    […] There as several ways to cuff your jeans (who knew!). I like this visual tutorial I found on Advice from a 20 Something: […]

  56. December 9, 2015
    Angeles says

    I love this post, where did you get the purple booties I love them? Please share, if you haven’t already done so! :)

  57. May 23, 2016
    Nikkita says

    I love this post, it answered everything I wanted to know and more. xx

  58. September 22, 2016
    Cassie says

    The pictures look great. But I have trouble knowing the perfect size/depth when you do 2-3 large rolls. Is there a guide to use. Thanks

    1. October 25, 2016

      They are from Michael Kors, but unfortunately this post is a couple years old so they are no longer available


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