Happy almost-Friday, friends, and cheers to the long weekend ahead! We have one last (belated) Christmas celebration, and then we’re headed to the lake to usher in the new year with family.
It’s hard to believe another year has come and gone, and I’ve managed to create over 200 posts here! I’ll be recapping all my favorites next week, but thought I’d finish out this year with one of my most-asked style questions this time of year…how do you wear ankle boots with skinny jeans?!
And as is true with most of my Sugarplum Style Tips…my biggest advice is not to overthink it! There really are no rules when it comes to boots and jeans, or how you cuff them. It’s mostly a preference thing. I’ve styled two basic outfits to share my tips, starting with this favorite relaxed cowlneck (currently 40% off!).
Cowlneck Sweater (40% off!) | Jeans | Ankle Booties | Tassel Earrings | Belt | Sunglasses
Cowlneck Sweater (40% off!) | Jeans | Tassel Earrings | Belt | Sunglasses | Cuff Bracelet
And while there are no right or wrong ways for cuffing, some are definitely more flattering than others! When it comes to ankle boots (basically any boot but knee-high or over-the-knee) and skinny jeans, I’m not a fan of tucking your jeans in the boots, or pulling them over the top of the boot. Leave those looks to tall boots and bootcut jeans.
The goal is to see at least a sliver of skin between the boot and hem of the jean.
Depending on the length of your jeans, that likely requires some sort of cuff…and there are several to choose from, depending on the look and style you prefer.
*The Slouchy Cuff*
Most skinny jeans are tight enough to hug the leg, so you can do a single cuff and let the rest of the length scrunch around the ankle. This look is casual and effortless.
*The Wide Cuff*
Fold the excess length up in a single wide cuff, making sure the cuffs are fairly even on both legs. This looks best on tall or leggy girls, as it can visually shorten the legs.
*The Messy Roll*
Fold the jeans up in a single, wide cuff, then fold them up again so the cuff is smaller, but the hem of the jeans are still exposed. This is how I cuff my jeans 99% of the time.
*The Double Roll*
Just as the name suggests, simply fold the hem up twice, creating a clean, even cuff. This style is is a more tailored look.
If you prefer a simpler method, or don’t like to cuff at all, choose jeans with a shorter inseam, or have them altered to ankle-length. Most of my jeans are a shorter inseam like these, and just require a simple, messy cuff.
Mockneck Sweater (under$50!) | Distressed Jeans | Ankle Booties | Sunglasses | Leopard Belt | Earrings
Mockneck Sweater (under$50!) | Distressed Jeans | Leopard Belt
Mockneck Sweater (under$50!) | Distressed Jeans | Ankle Booties | Leopard Belt
I hope this post was helpful and gave you some fresh ideas for cuffing your jeans with ankle boots. What method do you use most? See more of my Sugarplum Style Tips here.
I hope your holiday has been joyful and merry, and you have a safe, healthy and blessed New Year! I’m so thankful for each of you, and excited to continue this journey together! See you next week for a look back at 2017, and my favorite posts of the year.
Until then, don’t forget about the amazing Half-Yearly Sale at Nordstrom, and the unbelievable prices on a huge selection of in-season staples, including this long cardigan, these buffalo plaid lounge pants, Ugg slippers, and all these booties! Happy New Year, lovebugs!
{Fave Ankle Booties (all on sale!)}
{Huge Sale Alert on These Wardrobe Faves}
*Photos by the darling & talented Mary Summers. This post created in collaboration with Nordstrom, but all styling, tips and bowleggedness are my own. Thank you for supporting Hi Sugarplum sponsors!*
Thank you for the tip! I’ve actually never worn ankle boots with skinny jeans just for the reasons you pictured and mentioned, haha! 🙂
Charmaine Ng | Architecture & Lifestyle Blog
http://charmainenyw.com
Perfect tutorial! Very, very helpful. Like wow on both looks, but the burgundy sweater w/the suede (my weakness-sigh) booties, beyond amazing look. So hip, modern and just plain cool! Killer sales going on right now.
Your Christmas Crack-oh my GOODNESS! I say, All Year Round Crack-naughty and nice!
Thanks for enlightening us, Cassie.
Great post!
This is a great post, thank you. However… I’m in Canada with the windshield today it is -36 Celsius so there is no leg exposure whatsoever. Socks and warm boots are the best fashion accessory with our weather. Stay warm in Texas and take care.
Whoa, that’s cold!! For sure this doesn’t apply to everyone year-round!! I’d be in 18 layers and knee boots in that kind of cold!!!
Do you wear any low-cut socks ever? I love your look, but my feet don’t do well in just boots.
Sometimes I go without, but usually I wear no-show socks…these are my faves: http://bit.ly/2zvweNy
what if you don’t care for skinny jeans, I’m more of girlfriend jean wearer. how do you wear booties with girlfriend boyfriend jeans?
I would cuff them the exact same!!
So cute. But I have the same question as Angie. Do you wear really low-cut socks, or go without?
Sometimes I go without, but usually I wear no-show socks…these are my faves: http://bit.ly/2zvweNy
Love the post, personally I like the double roll look.
Such a wonderful post! I like the messy roll the most!!! Great visuals!
Must have those gold earrings. Where can I purchase? Love your blog. Happy New Year!
They’re Bauble Bar! http://bit.ly/2zAsxWL
I live in Michigan where it’s been snowing for ten days straight. Yesterday we received 14.7 inches of snow in a 24 hour period. Also did I mention it’s 9 degrees? Skin exposure just isn’t going to happen and I’m not wearing snow boots everyday. While they(the snow boots) are great for outside, they are really not enjoyable inside, and carrying around your boots inside is no fun either. So we tuck, and we will continue to tuck. I guess us northern girls will have to have a big red X on our fashion. Honestly I find the red X kind of offensive. We can’t all live in the south.
I’m sorry you found my post offensive, it certainly wasn’t my intent…it’s just general style advice for a question I get all the time, not cold-weather advice. If I lived in the north, I probably wouldn’t be wearing suede ankle boots! xo. C.
No, your post wasn’t offensive, just the red X in a comical sort of way(don’t want to be a fashion don’t)! Sorry if that transpired wrong! We just have no choice but to wear things tucked in/over the outside! Still wear suede in the winter(heels too!), we just treat it with scotch guard and walk carefully! 😉 xoxo
…and upon rereading my original comment post it does sound “bitchy”. My intent was not that at all. Sorry! Sometimes when we type we have a smile and a joking manner behind it, and when you go back a reread you realize that was not what came across. Unfortunately you don’t know me and I don’t know you, but if you did you would know that there was no intention of a mean comment.
I live in Michigan too and did not find this post one bit offensive! Don’t understand why some feel the need to express negative comments when someone else is just trying to pass along their opinions and helpful advice. I found this useful and have shared it with a couple friends who have also wondered about this. Thank you!
I know these are the current fashion “rules” but the look really isn’t flattering on a lot of folks. It makes my legs look very stumpy. Leaving skinnies uncuffed really helps to lengthen my leg line. I like to think we have left the rigid rules behind!
Definitely no rules…these are just some tips for cuffing and guidelines for people who like them! Fashion is meant to be fun!
What size are you wearing in the burgundy mockneck sweater? Thanks!
Great post Cassie… Love the skinnie tips with ankle boots! Super helpful…
Looks better tucked in with the black boots, because of the dip at the front….if they went straight across then the folded up look would work better.
Love the beige boots. Where did you get them?
Those are several years old from Nordstrom. xo
My personal opinion. Looks messy (like rolling up pants that are too Long and you don’t have time to hem). I prefer a more polished tailored classy look. To each his own , You do you.
I have always tucked my jeans in but leave a slouch. And I’m from the south (some commented on weather). I do have one pair of ankle boots that I don’t tuck because they look funny… I really like to wear crazy socks with some. It all depends on the outfit, my mood, etc. Whatever you think is best, who’s to say you’re wrong? (I started painting my fingernails with one nail a different color YEARS before it became a “thing”!!) But personally, I do think that ankle boots with capris look pretty ridiculous!!
Im shocked at how much this helps me. lol. I honestly am just into thigh high boots, or at least knee high, and after purchasing my first legit pair of booties, I felt everything I put on looked so dumb! Thanks for the styling help! <33
Well you are so welcome! I’m thrilled this post is still helpful! xo, Cassie
Lots of folks in the North wear ankle boots, even when it’s quite cold.You tuck them in, cover the top, or wear socks/tights that cover any showing skin. It isn’t a style faux pas to wear ankle boots and jeans without a cuff. I think you’re just describing a way you like to wear them.
Hi! I never mean to insinuate that ANYthing is a style faux pas! Of course this is just the way I like to style my ankle boots… in north Texas, we don’t have to worry about it being freezing *that* often! You Northerners have to bundle up! xo, C
If you can’t wear heels, you just are in allowed to wear boots