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This is a mistake I’ve seen way too often, haven’t you? You love your outfit, try to add a little edge by rolling up your pant leg, and instead look like you just stepped in a puddle and this was your last resort. Believe it or not, there is a right way to roll your jeans. It depends on the cut of the jean and what kind of shoe you’re wearing. Whether you’ve got on skinny jeans with flats or boyfriend jeans with booties, there are a few ways to roll your jeans for each look. So take a look at these options below. Warning: this post may make you want to go shoe shopping. :)
Skinny Jeans with Flats:
Skinny Jeans with Booties:
Skinny Jeans with Heels:
Always Roll 2-3 times for Straight Leg or Boyfriend Jeans:
How to roll your jeans when wearing boots:
One last thing…when it comes to boot leg, flare, or wide leg jeans, don’t bother trying to roll them. They look messy and are meant to be worn how they come!
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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!
Alyssa
The Glossy Life
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!
Amanda Says
Post authorThe brown and black ones are from Dolce Vita! You can find them here. The tall brown ones are from Aldo last year. Glad you like the post!! xx
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).
Sandy a la Mode Says
I LOVE rolling my jeans!!! thanks for these tips!!! pinning this now! :)
xo,
Sandy
Sandy a la Mode
Jeanine Says
Please share who makes the wine suede booties. Adorable!
Amanda Says
Post authorThey’re by Michael Kohrs! They’re super comfortable too – I love them! You can find them here.
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,
Ashley
SideSmile Style
Kb Says
This is so useful thank you! I never wear jeans much as I’m slightly scared of the whole ankle situation!
Mandy DeTurk Says
Those pink heels are awesome!!! Thanks for the awesome tips, I’ve always wanted to know how to do this, properly!
maria Says
I love this, it answered all of my questions!!! thank you!
tim Says
can i borrow your hands to roll my jeans
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!
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.
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!
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.
Tammy Says
What about wedges
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Sarah Says
Great post, and I have those same boots in the last picture. Love them!
Amanda Says
Post authorThanks so much! Aren’t those boots the best?? Wearing them right now!
Emily Says
Love the post, where are your jeans from????? So cute!!!
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Shelby Says
How would you recommend to roll skinny jeans with converse tennis shoes? I’m just wondering…
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For Girls Says
wow, great Tip thanks a lot!
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great post love it!
Gypsy Dharma Says
Very good tip!! We just tweeted this out :) Thank you!
Gypsy
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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!
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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!
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And with this post, I am officially in love with this site.
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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.
Amanda Says
Post authorSuch a great idea! The tight roll must have been before my time! I’ll have to check it out :)
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Keeping your jeans in your boots? Get jeangrabbers on jeangrabbers.com Great $12.95 best ever
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I rarely comment, however i did a few searching and wound up here How to
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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:
http://www.whowhatwear.com/how-to-cuff-your-jeans-like-a-pro
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Catherine Says
I never roll my jeans, but this post might have just encouraged me to give it a try!
Catherine
http://www.thesinglediaries.com
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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!!
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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! :)
Amanda Says
Post authorThey are from Michael Kors, but unfortunately this post is a couple years old so they are no longer available!
Nikkita Says
I love this post, it answered everything I wanted to know and more. xx
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
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They are from Michael Kors, but unfortunately this post is a couple years old so they are no longer available
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