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How to Style Ankle Boots + Non-Skinny Jeans
(Bonus: Warm Ankles!)


Baby it’s cold outside.

As I’ve made the transition from fall to winter weather, one of the questions that has nagged me the most has been how do I keep my ankles warm? In this age of mules and cropped jeans, some of us forgo the warmth. But I am not one to suffer (too much) for style, so I have been doing all I can to keep my ankles warm. That involves the obvious factor: boots, but where does it go from there? Often pants are cropped or boots are low cut, leaving exposed flesh on the coldest of days.

The good news.

As denim styles are evolving there is a new, simple way to style ankle boots and jeans, other than the ‘boots and skinnies’ formula we’ve all come to love over the last few years. We are in a time of cropped pants, often with a straight, boot or wide leg opening. This begs the question, how on earth do our beloved ankle boots fall in line with these styles?

I’ve been experimenting with styling my boots with wider, cropped pants and jeans, and I really like the look. (I first tried it a few years ago, but was mostly too chicken to try it again until more recently) I’ve taken to Pinterest to find the best examples for some guidelines and get your creative juices flowing.


How to Style Ankle Boots with Non-Skinny Jeans


1. Plan to tuck them under your jeans.

Note that the many of the boots used in these examples are snug-fitting around the ankle and shaft, but it doesn’t have to be that way. The third photo is a great example. (Click to enlarge.)

Source: 1 / 2 / 3

2. Hemlines of pants need to be cropped to the ankle, or shorter, to show off the boot.

Unless you’re going for a very 2000’s vibe, cropped is the way to go. Trust me, I tried it. I felt like I was in high school again, and I didn’t love it. Plus, then you’d be hiding your super cute boots under jeans. Not to mention, how many of us have full-length flare or bootcut jeans already?

Source: 1 / 2 / 3

3. If the hemline is so short that it creates a gap at the top of the boot, try similar-toned socks to fill the gap (and create a cohesive look).

I just started experimenting with this one. I like the monotone socks from the first two looks (which are admittedly close to skinny jeans, but finding sock examples eluded me), and I really love the navy socks in the third photo. It’s a great way to add visual interest to an outfit without feeling too busy.

Source: 1 / 2 / 3

4. Straight leg/demi boot cuts are the most versatile.

This style is the most versatile because it’s still leg-lengthening for a crop, which means you can wear it with a variety of shapes on top and still look balanced. It’s also a little warmer than wide pants because: drafts. I like the variety here of rolled hems (a great option if you don’t want to commit to chopping) and raw edges (great for texture!).

Source: 1 / 2 / 3

5. Wide leg pants work best with a heeled boot.

I still try to sneak in my flat high top sneakers with my wide pants though. Sometimes I love it, sometimes I feel like a kid. My number one option for foot wear with wide pants in the winter would probably be clogs with socks or clog boots.

Source: 1 / 2 / 3


Real Life Examples:


Shaft height is another factor that is helpful when styling ankle boots under jeans. The taller the shaft, the warmer the leg, and the more easily it will tuck under the pant. However, a taller shaft is not necessary. I’ve easily made some of my shorter-shafted boots work with the help of socks, namely my brown booties, which have been my most worn shoes lately. My chelsea boots work really well under jeans because they have a snug, elastic shaft around the ankle (this also keeps them extra toasty!). My heeled boots are some of my favorite to wear with cropped jeans, but I usually only pull those out on my ‘fancier’ days.

I’d love to hear how you’re styling your non-skinny jeans! Are your ankles warm? As always, thanks so much for reading, and being a part of this little community.

32 thoughts on “How to Style Ankle Boots + Non-Skinny Jeans
(Bonus: Warm Ankles!)

  1. This must be a regional thing. Fashion and weather and our responses are an interesting observation…I live in Michigan and there comes a point right about now that lasts through February where detailed fashion expectations like this go out the window, lol. It’s 26 degrees this morning and snowing. I’m wearing my navy ponte pants and black boots, with pink wool socks… #sorrynotsorry. It’s even worse after weeks of snow, plows, and shoveling, and everyone has a salt line on their pants from getting out of their cars. Winter fashion goals are always fun (how many sweaters can I wear and still pull off my vibe?!) but at some point we all lose the salty-pants and hat-hair battle, and then we just don’t care anymore :P

    1. Ha, I hear ya. Except for here, I feel like our battle is always against the rain. ‘How can I not look like I am hiding under raincoats 24/7 when I really am?’ I am very practical when it comes to my clothing because I like to be comfortable. That said, I still love to explore how to style myself in all weather conditions. ;) Currently: living under a giant down sleeping bag coat. ><

  2. None of these looks spell winter in NYC ..more like Autumn. The day after New Years til St. Patty’s I’m living in nothing but fleece leggings , oversized Jumpers & faux fur lined boots. #sorrynotsorry.

    1. I have the opposite problem over here in San Diego – I’m still waiting for the temps to drop enough for boot to enter my wardrobe!

      1. SAME! Miami here and we are going down to the LOW 50’s this weekend. I am beyond excited!! :)

    2. I am not a big leggings person, but I do love me some wool tights, which are warmer than a lot of my pants! Yesterday I wore wool tights under my denim jumpsuit, and I was nice and toasty! I think it’s all in the layering! I love Polly’s comment down below.

  3. Such a great compilation of inspiring looks, Andrea! This is definitely a style combination I’ve been thinking about as I adjust to my new cold-weather climate.

    1. Erin, I need an update!! What a big shift in weather and culture even. I hope you are having a great time so far! (And not freezing!)

  4. This is exactly what I needed! I’ve been struggling with it this fall/winter especially since my love of the wide-leg cropped pant bloomed this year. Thank you so much Andrea for the inspiration! Now, to find some good boots.

  5. I really got a lot out of this post! Thank you. When proportions change in fashion, there’s always the trick of how to make it practical for real life!

    1. Agreed! If it’s not practical, I just feel silly! I can’t stand not being weather-appropriate, so I am always overthinking this stuff. ><

  6. Loved this post! It’s awesome! So helpful for people like me who are late into the wide leg cropped pants trend that is better suited to other seasons… good job!

  7. I still haven’t exited the skinny jeans wagon, but you’re starting to pull me away! Wider-bottomed jeans/pants definitely seem harder to style shoe-wise, and I’m not 100% convinced that they’ll make my hips look any less wide. The inspirations you’ve put together are spot-on, but just not for me (yet?).

    1. Krystal, I think skinny jeans will remain a ‘classic’ look. If you love them, keep rocking them! I just don’t love them on me because I have thicker lower legs/ankles, so sometimes they are uncomfortable or don’t look right. I also have big feet, which skinny jeans tend to emphasize. As always, follow your instincts!

  8. Knee length wool socks – that’s my solution to be able to wear my wide leg pants in an English winter (currently hovering around 0 degrees.) Sometimes, i’ll add knee length boots underneath for extra cosyness! I think Brits learn how to layer from a young age: i’ll always be wearing several tops ( thermal layer, long sleeve t shirt, sweater) and then long socks or tights under my trousers and then a coat, scarf, gloves and hat on top. When you go inside or on public transport, you can shed a layer or two: in winter, my handbags get bigger, to be able to hold discarded layers…

    1. Polly, what an insightful comment! I think I miss the right amount at the base layer sometimes. I always think of layering as sweater and up. And the big bag, totally makes sense! Let me ask you about your coat situation, I’ve been mulling this over a lot lately. I have a long down parka that is very warm. I like the look of wool, but those coats never seem as warm! What is your top layer like?

      1. Hi Andrea, I have a long puffy down coat, like you, for when it’s cold and also wet and then I have a black wool duffel coat that I love and a pale wool overcoat (risky, as I’m clumsy with coffee – but I like a bit of lightness in the dark winter months) for days when the forecast’s fine. The UK climate is notoriously changeable, but having two wool coats means that if one gets wet, I can let it dry and wear the other. Both were thrifted: Brit charity shops tend to be treasure troves of quality coats. Natural fibres (wool, cashmere blend, vintage camel hair) in thick weaves seem to be durable: mine have lasted 6 or so years. And I have a couple of beanies, gloves and a few scarves to brighten things up and add warmth…

      2. Fellow Brit, totally agree layering and natural fibres. A silk Cami add an amazing amount of warmth for such a flimsy piece (silk thermals are amazing too), then a silk or brushed cotton shirt, cashmere of wool jumper or cardi and a wool coat on top. Down puffa if it’s really cold. Can you get more British than a duffle coat? I love my Gloverall one

  9. I froze my toes off all day in loafers today, this inspo is perfect timing! Most of my boots have a low shaft, so it requires just the right socks to show off with cropped pants. Do you have a favorite spot to get cute, wintery socks that are more neutral? I love the looks with a slightly taller boot, and it feels like those might be more practical for deep winter. I wish Everlane’s Boss boot was just a bit taller, it’s so close to what I’m looking for!

    1. Hi Bev! I haven’t bought any socks yet this year, but last year I got some merino wool socks that I really like, and I bought my mom some Smartwool socks that seemed really nice too. Both are from Nordstrom, and made in the USA. (And those are affiliate links, just an FYI.) I think Smartwool has some warmer-toned shades as well!

  10. Really cute examples! Where did you find all of them? I’m in an area that gets super windy with a damp cold, so it’s all about warmth and covering exposed flesh for me. I’m going to try the sock thing with boots/cropped pants more often, but I’ll admit, it sometimes feels like I’m committing a fashion faux pas!

    1. I found them all on Pinterest! If you want to examine them further, all the photos are linked to the pin underneath the photo. It is damp cold here too, with all the rain. But I swear, it feels colder this week with the sun out and no clouds to cover us!
      Honestly, when I am all layered up I feel like a fashion faux pas too sometimes. But then I remind myself that I’m not cold, and I don’t worry about it too much! ;)

  11. Perfect timing! I just ordered the Boss Boots in burgundy. I’m thinking they will look really good with my ABLE vintage jeans and a slim top. I am also hoping the color works with my Kamms (midnight). And also with tights and dresses. Fingers crossed :)

    I also love the tonal sock trick and used it a lot in Paris last year (February). Worked like a charm – style + warmth.

    1. That sounds like a GORGEOUS combo. I really, really like my boss boots. They are way more comfortable than the modern heel boots I got last year. The burgundy is gorgeous! I hope you get lots of use out of them. I imagine they will look great with your Kamms!

  12. I thought I was the only person who had cold ankles!! Thanks for the pictures and inspiration! Now to find those jeans…

  13. Andrea I am so inspired by your style and your realness! I thrifted a pair of eggplant bootcut JCrew cords which I cut to the cropped hem and paired with a Grey suede block heel Sorels! Waterproof and lined!! Warmth secured which is critical here in Wisco. The cropped flare hemline has not hit yet here in Madison so I feel like a trendsetter!! Would love to upload a pic but not sure how.

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