Happy December! And welcome to part one of a two part series, all about how to wear ankle booties with jeans.
Today, we’ll look at three different pairs of booties and approach styling them by boot shaft height — short, medium, and tall. (Here’s a quick visual, if you’re not sure what I mean by boot shaft height.) For each pair of booties, we’ll look at four elements — the booties, the jeans, the roll, and why it works.
Then tomorrow, in part two, we’ll look at the same booties, but we’ll add warm, wooly SOCKS! So that’s exciting.
You ready? Let’s jump in.
First things first: We can all relax. Because there’s no right or wrong way to do this.
Truly.
I mean, sure, sometimes one particular jean-rolling technique gets labeled “right” and another gets labeled “wrong.”
But … it’s all invented anyway, right? And we all prefer different things, right?
So try things out, play a little, but go with what works for you in the end.
ONE: Short
The booties: Minimalist ankle booties by Fortress of Inca (similar for less here). Three and a half inch shaft height. Three inch heel.
The jeans: Full length skinny jeans by Joe’s Jeans (old — similar here)
The roll: Deep cuff, about three to four inches tall.
Why it works: Take a look at the photo on the right. Notice the nice little dip, right there in the front? It kind of makes a “V” shape when you’re looking at the bootie straight on.
Well, that front dip or “V” shape makes these booties 100% versatile when it comes to how to roll and what jeans to wear. It also means they are super flattering — AKA they give the appearance of longer legs, and look good on just about everyone.
When it comes to booties with the front dip, I prefer a good bit of ankle showing. That bit of skin really highlights that dip and flatters the ankle.
Since these jeans are full length — not ankle length — I went with a deep cuff. I’ve been into it lately, because it’s just so easy. Plus I wear a whole lot of heeled shoes in the fall/winter, and the deep cuff works particularly well with leg-lengthening heels. (If paired with flats, the deep cuff can make the leg appear shorter. That hasn’t stopped me from wearing it with flats anyway, but still, something to note.)
TWO: Medium
The booties: Boho ankle bootie by Sam Edelman (old — similar here). Four and a half inch shaft height. Two and a half inch heel.
The jeans: Full length boyfriend jeans by Rag + Bone (old — same jean in a different wash or similar for less)
The roll: Messy half roll.
Why it works: Boyfriend jeans were made for the messy half roll. Slouchy jeans with a slouchy cuff? Yup. I like to leave a little bit of skin showing, but not much, especially when it’s chilly.
Here are three quick steps to the messy half roll:
- Make one deep cuff, about three or four inches tall.
- Grab the bottom of the cuff you just made — one hand on the inseam of your jeans, one on the outseam. Roll the inseam up for a second cuff, while holding the outseam down.
- Fuss with it a bit and — here’s the secret — make sure the hem of your jeans is still peeking out a little above your messy cuff.
Need visuals? Here’s a whole post on the messy half roll.
THREE: Tall
The booties: Rugged ankle booties by Timberland. (Fit note: Runs small and narrow. I sized up half a size and got the wide width.) Six inch shaft height. Three inch heel.
The jeans: Full length skinny jeans by Joe’s Jeans (old — similar here)
The roll: Deep cuff, about three to four inches tall.
Why it works: These booties really threw me for a loop for a while. Do I show skin? Tuck my jeans in? Nothing looked quite right with that tall shaft.
Until I tried my old standby: the deep cuff.
I like it because it doesn’t show skin, but it’s also not technically tucked in. It’s more like the cuff is just perched on top of the boot. And that, right there, is the key to this look.
Now, when you try this, expect your jeans to do their own thing throughout the day. One leg may end up tucked in at some point. The other leg may still be perched. They won’t always be even throughout the day. But that’s why it works — it doesn’t take itself too seriously and it’s not perfect.
• • •
Tomorrow, we’ll look at the same booties — but we’ll add warm, wooly socks! That’s right, no more cold ankles. YAY.
So tell me, what’s your favorite way to wear your ankle booties with your jeans? Got a low-maintenance roll that you always go to? And I’d love to hear if you’ve mastered a different way to style a tall shaft bootie, like #3. Share away!
xo,
Susan says
December 1, 2016 at 9:10 amI have a simple question – what socks do you wear with low cut booties? I haven’t found low cut socks that stay put over my heal but I don’t want to wear taller socks that show over the top of the bootie.
holly says
December 1, 2016 at 9:58 amI’ve found that buying sport athletic socks that hit at the bottom of the ankle bone but above the shoe line… in the largest women’s sizes…NOT regular women’s size like 5-9, but more like 8-11, helps them stay put.aka… No sliding in my boots. The elastic plus the bigger size in the footbed makes all the difference. I try to buy Made In the US, and socks are easy to find made in the US if you look! No Nonsense is the brand I buy…
Christine says
December 1, 2016 at 11:45 amMy husband discovered Darn Tough socks and showed me their ladies category- their ‘no show’ socks ALWAYS stay put- they’re comfy and if you destroy them, they replace them for free. Well worth the price.
https://darntough.com/collections/women
Kate says
December 1, 2016 at 11:51 amSusan, I had the same problem and was frustrated that those little socks would slip off and bunch up around my toes. This summer I found the Hue ultra low cut no show liners (scored them at Nordstrom Rack) and they seriously stayed put. Rarely had a problem with them.
http://www.dsw.com/handbag/hue+ultra+low+cut+womens+no+show+liners+-+2+pack?prodId=258356
Alice says
December 1, 2016 at 12:16 pmI bought some gold toe ankle socks. They stay put and are a bit thick, which is nice in cooler weather or for shoes that I bought intending to leave room for thick socks!
Kristen Coppola says
December 1, 2016 at 2:01 pmJust butting in here, but I am a huge fan of smartwool socks with my low-cut booties when I’m not wanting them to show. They’re expensive, but they last for years. While the promo images make them look like they would show, I’ve never really had a problem with that. If I put my booties on and they’re sticking out, I just readjust a bit, and voila. Here are some links.
for warmer weather: http://www.smartwool.com/shop/womens-phd-run-ultra-light-micro-socks-sw0sw188?variationId=039
for cooler/cold weather: http://www.smartwool.com/shop/womens-phd-run-light-elite-micro-socks-sw0sw210?variationId=044
But I’m also excited to hear Caroline’s input, because I love socks of all sorts. :)
Caroline says
December 1, 2016 at 11:51 pmHey Susan, I actually don’t wear socks with my booties until it gets cold. Most of the year I’m fine without. I like everyone’s recommendations, and I’ve also heard good things about the liner socks with silicone on the heel that helps the sock stick to your foot a little bit. (http://bit.ly/2gMInEt) I’ll list other favorites in my post tomorrow.
Taryn Beachler says
December 2, 2016 at 1:39 pmDon’t your feet get sweaty with no socks?
kelye Gwaltney says
December 1, 2016 at 9:16 amHey Caroline! I’m obsessed with your blog and use it as inspiration constantly. Please send me your closet it is absolute perfection!!!!!!!!!!!!!!!
Can you put together a gift guide for family members? I’m strugglingggggg.
xoxoxox <3
Kelye
Caroline says
December 2, 2016 at 9:40 pmKelye, I’ll think about doing something like that! Thanks :)
Laura says
December 1, 2016 at 9:20 amLove it, Caroline! I will have to try the tall cuff. I’ve always worried it will make my legs look short like you said. I imagine since you’re cuffing black jeans, it has less of the banded effect than blue jeans showing the light side.
Excited for warm socks tomorrow! I never show my socks, always cold ankles, so I’m interested in your ideas.
xo,
Laura @ http://www.thriveorsurvive.us
Caroline says
December 1, 2016 at 11:51 pmStay tuned, Laura! :)
lo says
December 1, 2016 at 9:23 amlove the look of number 2! I can never pull off the boyfriend jean so I am always envious of those that can. excited to read part 2!
XO Lo
thoseprettypieces.com
Caroline says
December 1, 2016 at 11:53 pmHi Lo, I had a hard time finding boyfriend jeans too (so saggy in the bum!) but the slim boyfriends have been perfect! Might be worth trying some different silhouettes :)
Tania /// HILLITA says
December 1, 2016 at 9:24 amI love this series! I used to avoid booties because I didn’t know how to style them. Couples with my athletic calves, I felt like tree trunks stomping around everywhere lol
But I’m fully converted! In fact, that’s my main shoe choice for my work capsule – and life in general. It’s so much more put together than running around in sneakers or flip flops. I can’t wait till you show us wooly socks because this is the one month in Dallas that we can wear them haha
Happy December, Caroline!
Sincerely, Tania
Caroline says
December 1, 2016 at 11:53 pmHaha Tania! Same here. Gotta wear them while we get the chance! :)
Esha vaid says
December 1, 2016 at 9:24 amHi Caroline, really helpful post and answers some on my questions on styling some newly purchased booties! I had a quick question on boot sizing. Do you always size up to fit warm socks or go with your actual fit. I got a pair of booties which fit well with thick socks but without the thick socks, feel like my heel is coming off just a tad bit.
Caroline says
December 1, 2016 at 11:59 pmHey Esha, great question. I usually buy boots in my regular size, since I don’t normally wear socks. If the boots are exclusively for cold weather and I want to wear thicker socks, I might go up half a size. If you’re having a problem with the heel, you might want to consider putting some moleskin padding (http://bit.ly/2fRK0fl) or a little heel cushion (http://bit.ly/2fMBiUE) to keep it from slipping. Hope that helps! :)
Esha says
December 4, 2016 at 9:33 pmThanks so much Caroline!
Heather says
December 1, 2016 at 9:36 amThank you, Caroline! I’ve been trying to find the right combo of booties and jeans for awhile… to the point I’ve returned 10 pairs this season because I can’t get the look right. Maybe it’s just too far outside my comfort zone? Or I need different jeans?
I’m fairly short with thicker calves, so I never feel that the look is elegant enough! (To be fair, I felt that way about tucking t-shirts in, but after I got brave and tried it, I got tons of compliments.)
Keep up the great work and happy December!
Kristine says
December 1, 2016 at 10:15 amI have short legs (especially shins) too and it took me forever to find a pair that I like on me! The trick was a really low cut in front (similar to the first boot that Caroline shared… But even lower!) these are my perfect bootie – and they’re on sale! http://m.shop.nordstrom.com/s/sarto-by-franco-sarto-granite-block-heel-bootie-women/4327880?cm_mmc=google-_-productads-_-Women%3AShoes%3ABoots-_-5149142&rkg_id=h-320bbed9e2c55ef680678eb383c8ea2e_t-1480605118&adpos=1o1&creative=145503081338&device=m&network=g&gclid=CNCFh_Gj09ACFYU2gQod3CII9A
Kim says
December 1, 2016 at 11:56 amJust another bootie suggestion! (these are especially good for high arches/wide feet) They are as comfortable as sneakers! And have that beautiful V in the front that flatters the leg:
http://www.zappos.com/born-michel-black-full-grain-leather
Kate says
December 1, 2016 at 5:08 pmI bought these in the brown and can definitely attest to the comfort :) love them for when I’m doing a lot of walking!
Christy says
December 1, 2016 at 10:10 amLove the tall shaft boots from Timberland! Can you tell me- are these the dark brown or the medium brown ones?
Thanks!
Caroline says
December 1, 2016 at 11:26 amHey Christy! They are the dark brown ones — and go perfectly with my FashionABLE saddle bag! (http://bit.ly/2gcbo8T) :)
Christy says
December 1, 2016 at 12:48 pmThanks, Caroline! I just ordered both following links from your blog :)
Caroline says
December 1, 2016 at 1:42 pmYay! Thank you for the support! :)
Marie Therese says
December 1, 2016 at 11:03 amI usually do the third option with my ankle boots. I like the way it looks – not too neat and like you didn’t try very hard (which I don’t! ;)
Alyssa says
December 1, 2016 at 11:45 amI love the tall shaft boots with my J. Crew high rise skinnies — I have a pair of Frye Sabrina 6G boots, and I tuck in the jeans to the boots, or wear cozy socks and give one roll so the socks show through. The jeans have about a 29″ inseam and hit me millimeters above my ankle, so no rolling necessary unless I want a more cropped look, which works too. For me, I’m more of a preppy/artsy type, and I like my bottoms fitted with loose tops, and I find that the tall shaft is most flattering for that silhouette (at least on me!)
Caroline says
December 2, 2016 at 12:02 amAlyssa, I love those boots! I bet they look so cute :)
Tanya E says
December 1, 2016 at 11:46 amNice ideas, it’s the little details… however it’s been skinnies tucked into long boots here as it’s been icy in the mornings here in the UK. I do wear rolled up jeans with ankle boots and chunky socks on milder winter days, but I will save the bare skin for spring!
STEPHANIE says
December 1, 2016 at 12:45 pmI have some taller shaft booties from Sam Edelman that I bought for a dress – I wasn’t sure how to pair them with jeans, but I tried your deep cuff this morning and it’s PERFECTION! Thank you!!
Caroline says
December 2, 2016 at 12:03 amYay Stephanie! Glad that worked. :)
joanna says
December 1, 2016 at 4:43 pmI actually prefer the non-roll. I like to pull on my chelsea boots and wherever the jean hems lands, it lands. I like the casual look it gives and actually like the bunching. It looks easy and always just falls right. I will say this technique only works with skinny jeans and a medium (maybe short) boot.
Caroline says
December 2, 2016 at 12:04 amSounds cute Joanna! Thanks for adding another suggestion. :)
Jessika Riordan says
December 1, 2016 at 5:37 pmHey Caroline,
I’m a 38 yr old mum to a gorgeous 16mth old boy. I live and work part time in Sydney, Australia and still continue to have a love of fashion and makeup!
My style has dramatically changed for the better since becoming a mum (surprisingly) and your blogs have been a major influence in my style choices!
Keep the beautiful, clever style blogs coming girlfriend!
Caroline says
December 2, 2016 at 12:06 amJessika! Thank you for the kind comment. Glad things are going well — especially as a new mom! From what I hear, it’s not always an easy style transition. Well done. :)
Heidie says
December 1, 2016 at 6:08 pmHey Caroline, thanks for such an informative post! Hoping you might do a similar series on how to style boyfriend jeans. Most of my wardrobe works great with skinniest but doesn’t always work with the loose cut of the boyfriends. I don’t want to buy new items just for the new silhouette but my current favs just don’t seem to work. So glad you’re back sharing your insights with the rest of us!
Caroline says
December 2, 2016 at 12:09 amHey Heidie, I’ll add it to my list of ideas. :) Until then, you can see a few ways I’ve styled my favorite Rag + Bone boyfriend jeans here: http://bit.ly/2geEJzG
Lauren says
December 1, 2016 at 8:09 pmThis is so helpful! I struggle with pairing my ankle boots with jeans– partially because i have really long legs, and jeans tend to run short on me making the pairing a little awkward at times. I’ve recently settled on pairing them with my full length jeans rolled once, and I like the effect. Looking forward to part 2!
-Lauren
http://www.chic-ethique.com/
Maureen says
December 1, 2016 at 11:46 pmI love those Fortress of Inca booties and bought a pair after seeing them on the blog. I am a size 10, but their 10 was snug on me in the toe box and I had a cobbler stretch them. I still find them uncomfortable, but they are so gorgeous. Like a work of art (the most expensive shoes I’ve ever bought by far). I have been wearing them with Peds. They give me terrible, terrible blisters if I don’t. I am hoping that as they age they will get more comfortable. What socks (if any) do you wear yours with?
Asia says
December 2, 2016 at 9:07 amLove this series, so useful!!!!
You always looks so polished with a minimalist wardrobe. Love your blog.
Alina @EclecticAlu says
December 2, 2016 at 10:14 amI find that boyfriend jeans tend to be difficult to pair with boots. This was very helpful!
Alina
http://www.eclecticalu.blogspot.com
Liesbeth Verlinden says
December 2, 2016 at 11:46 amNice suggestions, will definitely try the messy roll. I always just do a double cuff when I cuff… but for tall shaft booties I often just tuck my skinny jeans in (I have mainly superskinnies / jeggings). It looks less fashion forward or playful, but definitely sleek. Since I’m short, I don’t generally draw attention to my ankles or footwear :).
Wildfire Charm says
December 2, 2016 at 1:03 pmI love how you’ve paired these booties with jeans. I love wearing Jeans! They’re my everyday outfit pretty much so this was helpful :)
http://www.wildfirecharm.com
Emily R says
December 2, 2016 at 1:48 pmYES to socks! Thank you! I live in Colorado and some days are so cold you’d be insane to go without socks. So happy to see some styling for boots & jeans that includes warm wool socks. And your taste in socks is perfect – wool camping socks are the best! So worth the cost per pair!!! Mine have extra padding around the toes and heel to keep your shoes from irritating your feet, and I gotta say in those sub 30 degree days it’s so extra warm and cozy to wear them.
saru says
December 3, 2016 at 5:46 amVery interesting post :) Great blog!