It's so nice to meet you!
Get to know Kay...

How to Wear Straight Leg Ankle Jeans in the Winter

January 6, 2021

Hello! Welcome to Dressed for My Day, where my goal is to help you and me look our very best, even past 50. To that end I try to provide styling tips that will help us wear the latest trends in ways that flatter our bodies and reflect our personal styles. Right now straight leg jeans continue to trend. And while the ankle length version of those straight leg jeans are super flattering and fun to wear in spring and summer, they can be a bear to wear in the winter. Let’s see if we can nail down some ways to wear straight leg ankle jeans in the winter.

How to Wear Straight Leg Ankle Jeans in the Winter

First off, let’s establish that I’m no expert in this area. But I’ve done some research and I think I have a few tips for us all. Second, let me go ahead and state up front that not all of these looks will work for every person. I know, from having lived in four different states, that winters vary greatly depending on where you live. So please keep that in mind as you peruse these style choices and tips.

Finally, this post is compiled completely of looks that I pulled together from what I have in my closet. The photos aren’t great; they’re taken in front of a mirror in my office. But hopefully they provide a little closet inspiration for you.

The jeans I’m wearing in this post are these Modern Ankle Jeans from Talbots. They’re a great year-round jean if we learn how to wear them. So that I can focus on style tips, I’ll provide a shopping widget at the bottom of the post with everything else I’m wearing instead of providing links as I go. Let’s get started.

First up, a semi casual look with sneakers.

If you’re in a climate where you can bear your ankles, you’ll really have no trouble wearing your ankle jeans through winter. But hang with me because I have other style tips you’ll still need.

Ankle Jeans Cropped Blue Sweater Front Tuck White Sneakers
You could leave the top untucked here because the sweater is slightly cropped and it’s a similar color as the jeans.

Proportions, proportions, proportions. I cannot emphasize enough how important pleasing proportions are in creating an aesthetically beautiful look. Because straight leg ankle jeans are ankle jeans, they’re shorter. And that means most of us (depending on your personal body proportions) need to elongate them. We can do that several ways:

  1. Tuck or at least front tuck your top.
  2. Wear a shorter or cropped top that can be left untucked but that ends just at the waist.
  3. Wear dark boots under the jeans to elongate the lower portion of the leg.
  4. Wear a dark top, creating an elongating column of color.

You’ll see me do all four of these style tricks and sometimes multiple tricks at a time. When I don’t use any of these four style hacks, you’ll notice a big, not-so-flattering difference.

Styling Tip: If you don’t want to tuck in your shirt, then definitely wear a dark colored top so that you create a longer look. If you wear a light colored top and let it hang out, your jeans (and thus your legs) will look really, really short and squatty.

In the photo above I’m wearing beige suede ankle booties. Again, these will only work with these jeans if you can wear them without socks and still be comfortable. And you actually could wear darker booties the same way. But I like the more flesh-toned booties so that the look is more cohesive; there aren’t as many breaks. Know what I mean?

Style Tip: The trick to wearing your straight leg ankle jeans with your booties is that your jeans should end well above your booties, with as much as 1-2″ of space between the two. You want the space to look intentional, so you don’t want the jeans sitting on top of the shaft of the booties.

Ankle Jeans Cropped Blue Sweater Front Tuck PG Loafers

Style Tip: You can wear straight leg ankle jeans with most of your shoes during the winter. But flats such as loafers and ballet flats are definitely appropriate.

Again, above I wore shoes in a color close to my skin tone for a more seamless look. But these loafers do have pattern and interest. So don’t assume you have to wear solid nude shoes.

I want you to see that you absolutely can wear this particular sweater untucked with the cropped jeans because 1) they’re a similar color and 2) the sweater is slightly cropped. Actually, the reason we’re seeing so many cropped sweaters and tops these days is because they are great to pair with high waist jeans, and these Modern Ankle Jeans from Talbots do have a nice high waist.

Ankle Jeans Cropped Blue Sweater No Tuck PG Loafers

Style Tip: Straight leg ankle jeans work beautifully with boots that have a more narrow shaft that can fit under the bottom or your jeans comfortably. You can even wear socks with them!

Ankle Jeans Cropped Blue Sweater No Tuck Brown Suede Boots

You’ll see me wear different shoes with different sweaters and tops throughout this post. But in each outfit, my favorite footwear choice is the dark brown suede ankle boots above. They have a 5 1/2″ shaft that is narrow enough to fit comfortable under the jeans, creating a seamless silhouette. With these boots (or similar dark, high and narrow shaft boots) I don’t have to worry quite as much about where my top ends.

Ankle Jeans No Tuck Ankle Boots Blousy Sweater

In the above photo I’m wearing another cropped sweater. So I don’t have to tuck it to create the long leg. Especially if I wear my dark tall ankle boots. However, as you’ll see in the next photo, this sweater has very voluminous dolman sleeves, so a tuck helps the outfit looked more pulled together.

Ankle Jeans More Front Tuck Ankle Boots Showing Blousy Sweater
Ankle Jeans Front Tuck Ankle Boots

Don’t you think a little front tuck – even one off to the side a little – really helps “reign in” that sweater? It may seem like that has nothing to do with the ankle jeans. But keep in mind these are straight leg jeans, not skinny jeans. They do have a slender fit. But you want to do everything you can to balance out the fullness of the jeans, and that little tuck really helps create that pulled together appeal.

Ankle Jeans More Front Tuck Ankle Boots Blousy Sweater

And in fact, because this sweater does feature blousy dolman sleeves, I really prefer the full front tuck. But that’s just a personal preference.

Let’s move on to another type of top. I wanted us to see how to style the straight leg ankle jeans with a longer sweater, too. In the first frame I just put on the sweater with the straight leg ankle jeans and dark brown boots. I didn’t tuck it at all. And I guess you could do this, mainly because the boots are dark and help elongate the legs.

Ankle Jeans Full Length Beige Sweater No Tuck Brown Suede Boots

But watch what happens when I add a little front tuck. Actually, it’s a pretty thorough front tuck. Ha! But it is untucked in the back. And the front tuck is soft, with some give.

Ankle Jeans Full Length Beige Sweater Front Tuck Brown Suede Boots

That front tuck really makes my legs look longer. And while that’s optional with full length jeans, it’s crucial with ankle length jeans.

Ankle Jeans Full Length Beige Sweater Front Tuck Belt Brown Suede Boots

You don’t have to wear a belt, but I added on in the photo above, and I like the effect. But since we’re working on elongating and creating uninterrupted lines, I probably wouldn’t wear a contrasting belt.

Remember: All of these tips could change depending on your body proportions. My proportions are really pretty balanced. Learn how to dress your unique body proportions in my Dressed for My Day My Way series.

Finally, if you want to tuck to achieve those pleasing proportions, but don’t want to draw attention to your waistline, add an outer layer. Not only will a jacket camouflage your tummy, but it will create the illusion of more shape and slenderize.

Ankle Jeans Full Length Beige Sweater Front Tuck Belt Brown Suede Boots Leather Jacket

Below I’m wearing the same beige cashmere v-neck, still tucked in the jeans, with pumps. Of course, depending on where you are and your personal preferences, you may have absolutely no use for pumps in the winter. I get it. But every so often (like on my anniversary date) I do go ahead and brave the cold and wear mine. And they’re really quite lovely with ankle jeans.

Ankle Jeans Full Length Beige Sweater Front Tuck Belt Leopard pumps

Above I chose leopard print pumps (no longer available) to pair with my jeans and sweater because I like how they add interest to this “oatmeal” look. But you could wear any color or even nude pumps.

Putting on the pumps got me to thinking about creating a more office friendly look with the Modern Ankle Jeans. I styled my Talbots perfect white shirt next. Left untucked, this shirt works fine with the jeans because it has a tailored, feminine fit.

Ankle Jeans White Shirt No Tuck Leopard pumps

But tucking it in and adding a belt really adds some polish and definitely creates those more pleasing proportions. For the above look (with the shirt untucked) I think you’d really need to pull out the stops with some style hacks. Pop the collar, add a statement necklace and a pretty bracelet. But tucking and belting elevates the look instantly.

Ankle Jeans White Shirt Full Tuck Belt Leopard pumps

Don’t want to tuck, especially all the way around? Don’t forget about that layering piece. Add a loose fitting blazer and the focus will be on those pleasing proportions, not your tummy.

Ankle Jeans White Shirt Full Tuck Belt Leopard pumps Camel Jacket

Trust me on this. I do not have a tiny little waist. You can see that in this post. But proportions trump tiny waists. They really do.

Oh, and for those of you who prefer flats, here’s the look with my leopard flats. The heels definitely help elongate the leg. So I think it’ even more important to tuck the shirt when wearing flats.

Ankle Jeans White Shirt Full Tuck Belt Leopard Flats Camel Jacket

Can you untuck the shirt with the jacket? Well, let’s see.

Ankle Jeans White Shirt No Tuck Belt Leopard Flats Camel Jacket

Yeah, you can. This is not a bad look. But because the shirt and jacket are long and the pants are short, I’ve got more like 1:1 proportions. We want the top portion to be 1/3 and the body portion of my body to make up 2/3 of the outfit. So one thing that could help that would be returning to those dark brown tall ankle boots.

Ankle Jeans White Shirt No Tuck Belt Brown Boots Camel Jacket

So once again, shoe choice is key if you don’t want to tuck in your shirt.

But look what happens when I both wear the shirt tucked in and wear the dark brown ankle boots. Wowsa!

nkle Jeans White Shirt Full Tuck Belt Brown Boots Camel Jacket

Do you see how that looks so much more pulled together, cohesive, elevated? Now look, at our ages some of us have days when we really don’t give a flip about looking elevated. Ha! I get that. But if you know these style tools, then you can pull them out and use them when you want to.

I thought we’d try one more look. This time I’m wearing a basic black turtleneck sweater. I think of this as my Laura Petrie look. Ha!

Ankle Jeans Black Turtleneck Untucked Black Loafer

I’ve left the top untucked and I’m wearing black loafers to bookend the look. Other than the ankle space, the column of dark intensity is pretty much unbroken. So that’s a nice effect.

Add the camel blazer (or whatever you have in your closet) and you’ve got a polished, comfortable office look for a casual Friday. (The shirt is still untucked.)

Ankle Jeans Black Turtleneck Untucked Black Loafer Camel Jacket

But I like to tie this classic look together by tucking the turtleneck and adding a wide leather black belt.

Ankle Jeans Black Turtleneck Tucked Belted Black Loafer

And, since it’s winter, I can easily top the belted look with the jacket or other topper, concealing my imperfect waistline and creating the illusion of a slender silhouette.

Ankle Jeans Black Turtleneck Tucked Belted Black Loafer Jacket

This look is great, but better yet, add those dark chocolate brown boots for a truly chic look.

Ankle Jeans Black Turtleneck Tucked Belted Brown Boots Jacket

What happens if you take the jacket off? Here’s the look without the belt or tuck or jacket, but with the boots. That’s a great everyday look for winter, even though you’re wearing ankle jeans.

For the record, these are not my favorite jeans to wear when I’m just hanging around the house and doing nothing much. On days like that I do a lot of slumping on the sofa. Anybody? And these are not slumping jeans. Know how I mean? Hahaha! The high waist and slim fit are more conducive to sitting at my desk and knocking out work. So the is a great work from my home office outfit.

Ankle Jeans Black Turtleneck Untucked Brown Boots

Now, for my final look, I’m just elevating this combo a little more by adding, not a camel blazer, but a black leather blazer.

Ankle Jeans Black Turtleneck Untucked Brown Boots Leather Blazer

Yeah, that’s my luxury blazer (I did get it on sale), but you could create the same low-contrast-in-intensity look with a regular black blazer or faux leather jacket. It’s not the price of the jacket that elevates the look, it’s the low contrast in intensity and the head-to-toe column.

I hope you enjoyed today’s post. I get requests for posts walking you through the process of putting together an outfit, so I though this might be helpful. Let me know your thoughts in the comments section below. And thanks so much for stopping in today!

Shop the Post:

You can shop the look through the links in the copy above or through the shopping widget below. Sale prices are not always reflected in the widget, so click through to get pricing info. Remember, if you purchase anything through these links I potentially earn a commission, but at no cost to you. Thank you for shopping through Dressed for My Day. I am grateful!

Don’t Miss a Post:

If you like what you’re seeing here at Dressed for My Day, I invite you to subscribe to my email list. You can receive an email each time I post (about 6 times weekly) or just on Saturdays. You choose! But you’ll also receive the password to open up all the subscriber freebies I offer.

Blessed for My Day

When I see young moms wrangling their children through Target or the grocery store, I’m reminded of my own struggles when my kids were young. For the most part my kids stuck with me in stores and didn’t rebel too much. But they certainly had their moments of begging for what they could not have, touching things they should not have bothered, wandering off from me and just playing recklessly.

But when we left the store and wheeled the buggy (I’m from the South!) to our car, I insisted on 100% good behavior. I made my kids put one hand on the buggy and walk with me, not goofing off or running ahead. I required them to walk with me.

That, dear gal, is exactly what God requires of us today. Nothing more really. But nothing less either. We don’t have to steer “the buggy,” perform cartwheels or sit on the curb. He simply wants us to walk with Him, humbly submitted to His leadership, protection and direction.

He has told you, O man, what is good; and what does the Lord require of you but to do justice, and to love kindness, and to walk humbly with your God? ~ Micah 6:8

Spread the love
xoxo, Kay
Join the Conversation

This site uses Akismet to reduce spam. Learn how your comment data is processed.

33 thoughts on “How to Wear Straight Leg Ankle Jeans in the Winter

  1. My favorite is the outfit with the leopard booties. BTW…. I’m so glad that I have the Lord steering me in the right direction. Have a fabulous Monday. ~Lisa~

  2. Thanks for the styling tips. I wear straight legged pants all year around and love them. Probably because I can wear them with booties, tall boots and tennies. What I struggle with are flared jeans. I love them on everyone but feel like you need to wear them with heels and I can’t do heels. So if you have any ideas for me on hem, my ears and eyes are open!

    1. Thank you for this post! I have short legs for my frame and keep looking at myself, wondering what exactly is off about my outfit and now I know the key is to elongate. Your posts are always such a joy to read!

  3. I think the blazers, jeans, and loafers look sharp. I try to avoid heels. I do best in flats.
    You have such a flare and everything looks great on you!

  4. Great post and great outfit choices! Especially for our Texas winter weather where we don’t need warmth very often!! So many cute ways to style straight leg jeans!! This post makes me realize I need to have my straight leg jeans hemmed to work well with the booties! i’m short and my jeans usually just bunch up around the top of my boots! Guess I’ll make an appointment with the tailor!! Loved the Blessed for My Day today! A great reminder to just ‘walk’ with God! Blessings!!

  5. All of your jeans seem awfully short for winter. Do you wear petites? My straight leg jeans come down to the top of my foot or longer. I’m 5’6” and wear a size 6 or 8 so I’m not short. My skinny jeans are much shorter but too cold for winter unless I wear knee-high boots. I love all the looks you’ve shown but they won’t work with my longer jeans. I sometimes just end up wearing socks and Dansko clogs – ha! Thanks for all your help. I get lots of inspiration here!

    1. Hi Lisa. No, these are straight leg ANKLE or CROPPED jeans. They are made to hit just above the ankle bone. They’re great for warmer months but a little trickier to style in cooler months. Several readers had asked me to style them for winter. But I do have and love full length straight leg jeans, too.

      The skinny jeans you’re referring to are probably also ankle jeans, so they hit just above the ankle bone. But you can also get full length skinny jeans that are perfect for wearing inside boots or with booties or flats.

      I actually love straight leg FULL LENGTH jeans with clogs, too. ? Hope that explanation clarifies things a little. Thanks for reading!

  6. You have lots of great looks here and my favourite is the one with the leopard booties and vest. Today’s Blessed for My Day has a fantastic message. Thanks, Kay!

  7. Thank you so much for your help! I have worn skinny jeans for awhile and just started wearing straight legs pants again. I wrestled the other night before a dinner on whether I could wear my booties with them because it just felt awkward. Most days I wear my loafers with them but wanted a dresser look. In the end I wore different pair. So this post gives me so great advice for future. Hope you have a great day!

    1. Great to hear, Tanya. I’m so glad this helps. In the end you do just have to try on several things, perhaps, until you get the aesthetic you want. My biggest tip is simply do everything you need to in order to create longer lines. I think the benefits of this look, when done well, is a very chic, modern and somewhat edgy vibe. It looks like you’re more cutting edge than “the girl next door.” Know what I mean? Thanks for reading!

  8. This post is so helpful and timely! I struggle with jean/shoe choices in the winter months, so I’ll be referring to these tips often. Does anyone every wear black trouser socks with ankle jeans and black flats? I do sometimes – it SEEMS like it looks OK to me….but maybe that’s just me. Would really like to hear everyone’s thoughts.

    1. I did read one blogger who lived in Canada who suggested nude knee highs instead of socks. Makes sense to me. I prefer to reserve socks for boots and sneakers, lace up shoes or maybe loafers, but not ballet flats. But that’s purely preference.

  9. Hi, Kay! I’m 5’7″, (33″ inseam) so I’ve always struggled to find jeans long enough, so my ankles wouldn’t show and perceived as too short. I have to reset my brain! Do you ever cuff straight jeans? If so, how wide should the cuff be? Thanks for teaching this old dog new tricks!! You showed us some great options.

    1. The trick to ankle jeans as opposed to full length is that they need to be above the ankle bone. That way they look intentional and not like a poor fit. I prefer to have straight leg jeans hemmed to the length you prefer. In fact I just put on some today – still wearing them!! – that need to be hemmed. I’m going to have them hemmed so that they just graze the top of my foot/shoe when wearing flats or low heeled booties…I think! Such a tough decision really because then you’re kinda locked into wearing that shoe style/height with them.

  10. Thank you for the great visual reminder that we are to walk with God with just our hand on the ‘buggy’ and allow him to steer us!

  11. Thank you for the great tips with ankle pants in cool weather. It’s usually cold here for about 4 months so I wear black socks with black ankle boots with my black ankle pants. Sometimes I feel awkward, but it seems to work here. You do a great job, and I appreciate your scriptures too!

    1. Yes, I actually had a set of photos with my black booties too. But when I started putting the post together I couldn’t find them. Argh. But that’s probably quite fine to wear. Smart and a long line.

      1. I am curious to see the plaid blazer outfit with black booties instead of the beige booties. Seems like the “line” would be longer….maybe?

  12. Hi Kay: I follow you for looks as I am somewhat fashion dysfunctional but also because we share the same height ,weight and size. I don’t believe, however, that we are close in age as I am 76 years old.

    It’s hard for me to follow some of these fashion trends while trying to be fashionable, e.g. ankle length jeans; I think they cut you off like capris and make you look shorter and squatty. I think this whole thing of a French tuck is ridiculous and looks messy. Think how someone looks coming out of a bathroom and whose skirt is caught up in the back of her underpants. As for white tennis shoes, this was something a women wouldn’t have considered a fashion item years ago, and BTW, I wear a size 10 shoe so it definitely doesn’t look attractive. Same can be said for combat boots in a size 10, and forget Chelsea boots as I look like a giant elf.

    Another thing I am unhappy to see reappear is tucking your shirt/blouse in entirely and wearing a belt. Now we must once again walk around sucking our gut in trying to pretend we don’t have a middle spread due to age and childbirth. I so loved the top out and loose look.

    Sorry if I sound like a cranky old lady (maybe I am) but just wanted to give my take on today’s fashion trends.

    1. Lol! Well a lot of this is simply giving your eyes time to adjust to new trends. But you’re absolutely right. You do not have to or need to adopt any trends you don’t like. Sometimes I don’t like a trend at first and I determine I’m going to sit that one out – e.g. camo and mixing prints – but then later, as I see them more and more, I take the plunge and enjoy them.

      By the way, I wear a size 9.5-10 shoe, too. So don’t discount those shoe choices, especially if you also share my height and weight. You’re undoubtedly much more conscientious of your shoe size than anyone else.

      Thanks for sharing. Honestly, cropped jeans for winter are not my favorite choice either. But I did want my readers to have the tools to wear them well if that’s a trend they enjoy. And that’s why I shared tips to elongate the legs as much as possible.

      I’m so glad you’re a reader! Thanks so much for sharing your thoughts. ?

  13. I live in British Columbia, Canada and even though we don’t have temperatures as cold as other parts of the country where I am I think ankle jeans just don’t work here in the winter because it’s too cold to have any skin showing. I love full length straight jeans but have a hard time with the ankle version of them. I feel like I’m wearing jeans that got hemmed too short!

  14. Hi Kay! I love the BFMD! I would be totally lost without God at the steering wheel. Here in south central Georgia I am wearing my ankle length straight and skinny jeans now because we are not really having cold weather, yet. I have learned to take selfies so that I can really see how the shoes, jeans, etc., look together and then I can make any necessary adjustments. I think you did a nice job with the outfits you put together from items in your closet. I hope you had a great day!

    1. Yes! Taking outfit selfies is such a great way to dial in on the right proportions and other elements of a good outfit. Thanks for sharing, Ginger. ?

  15. I’ll tell you what photos are enlightening. Those taken by relatives at a family reunion. I found out the hard way, I really needed new bras. : ) I will try most trends if they fit my personality. Tucking in half a shirt or really tight pants are not my thing. I do wear my ankle pants in winter but I wear a boot topper with them. They have some cute ones I just bought a pair of fur ones. They cover the naked part and keep you warm.
    If you wear a black striped shirt outside a pair of black jeans with black boots, does that give you a longer line?

  16. I think you did a GREAT job of putting together these outfits Kay! Thanks for the tips along the way, too. And the BFMD truly blesses my heart today (a day after you posted). It’s a precious picture of walking with Jesus…and Micah 6:8 is one of my favorite verses. Thanks sister!

    1. Hi Karen, I’m not sure. Unfortunately, that happens occasionally. And that really bums me because I pay a pretty penny for that mail service. ARgh. But I checked the data base and your emails are going out. So there are a few things you can do. First check your spam folder. Then make sure you don’t have any kind of privacy settings on your email service that may be preventing them from coming in. Then make sure you have my email address – saved in your contacts list. If you do all that (I’m so sorry!) and you still don’t get an email in the morning by noon, then you may need to unsubscribe and resubscribe. Thanks so much for subscribing.