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.
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.
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:
- Tuck or at least front tuck your top.
- Wear a shorter or cropped top that can be left untucked but that ends just at the waist.
- Wear dark boots under the jeans to elongate the lower portion of the leg.
- 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.
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.
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!
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Can you untuck the shirt with the jacket? Well, let’s see.
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.
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!
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!
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.)
But I like to tie this classic look together by tucking the turtleneck and adding a wide leather black belt.
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.
This look is great, but better yet, add those dark chocolate brown boots for a truly chic look.
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.
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.
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!
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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
54 thoughts on “How to Wear Straight Leg Ankle Jeans in the Winter”
Love your Blessed for my day story & verse.
Hahaha! Thanks Holly.
Loved this post Kay. Seeing the evolution of the outfits and what different looks the styling tips create is very helpful to me. Thanks!
Great! Thanks for letting me know, Deanna. I wish I had better lighting and I would definitely do a lot more of these. We’re buying a house this spring and good lighting and white walls are at the top of the list of requirements! ?
You did all the work for us! Thank you!! I don’t know if my eye isn’t use to tucking clothes in all the way but I like a small tuck better. Maybe that is just my preference? it is great to see the looks compared to the other! Great post!!
Great. I’m so glad you like the post. Yes, I think the way our eyes have been trained has a lot to do with it. When I think about the black and white movies from the 40s and 50s and how the women always had their shirts completely tucked, I realize that we have just gotten away from that and our eyes are not used to it. So I think it’s good to stretch ourselves a bit, but we also need to style our looks in a way that makes us feel confident and not self conscious. So a front tuck is a great choice.
Kay – You knocked it out of the park with this blog post. Wow. I appreciate that you put a lot of thought and effort to pull this useful, comprehensive style guide together. It’s so thorough and honestly, really helpful. The visuals – wow. Thank you so much. Keep up the awesome work girl!
Good to hear. Thanks so much for letting me know that you enjoyed the post. ?
Great post. at 5’2″ and legs on the shorter side, these jeans would not be my favorite. I still benefited from all your style suggestions. I am enjoying your blog. Thanks for all you do to help us get dressed for our day.
Wonderful to hear, Anna. Thanks so much for letting me know. ?
Thank you for all of the visuals! I think we are all visual learners to some degree, and your comparisons are very effective! When I dress now, I think about proportions. At 5’3” and a short waisted torso, I love those cropped sweaters. Again, thank you for your time and talents. I always exhale when I read your quotes and Bible verses. ❤️
Yay! I’m so glad you are thinking proportions. I really think that is so crucial. Thanks for reading. ?
Thank you, Kay! This post was very helpful!
?? Thanks for letting me know, Kathi. I’ll try to do more like this.
Thanks for all the style tips but I Am always cold so I have to wear socks so the loafers and pumps are not practical for me. I usually just wear dark socks. Thoughts?
I just wouldn’t wear the ankle jeans with socks showing. But you can definitely wear socks with full length straight leg pants and jeans. And if you wear loafers and socks, I would consider using the socks as an intentional accessory. Maybe wear something like an oatmeal colored sweater, blue jeans, brown loafers and pretty marigold yellow socks to add a pop of color. ?
Great informative post, Kay! Love seeing the evolution of each outfit and how one little change can make a huge difference!! I know you don’t have the time but that would be SO helpful to see HOW you arrive at styling each piece for us in your posts. I have struggled with wearing the shorter straight leg jeans in the winter as well. My feet and ankles get so cold when wearing flats or loafers. Adding the right boot solves that problem!!
I’ll work on doing maybe one of these a week. I can’t really do them on a regular basis in my HIRDFMD posts because I’m usually in a hurry when I get dressed. But I can certainly try to intersperse some outfit evolution into my posts here and there. Thanks for sharing. ?
Thanks for sharing your tips!
You’re a sweetheart xoxo
I’m so glad you enjoyed it! ?
Helpful post, Kay!
Great to hear! ??
I’m STILL not ready to give up my skinniest and I think every one of these looks would be improved with skinny jeans, but I know that is just my personal preference….at this time. What I LOVE about this post is the evolution with so many choices! Thanks for the time and energy it must have taken! So appreciated!
Hahaha! And fortunately you absolutely don’t have to. They’re not out by any means. Just not quite as modern. And really you need to wear what looks best on your body and what makes you feel confident. ?
Thanks for all the tips on how to wear straight leg ankle jeans. The shoes do make a difference
on how the pants look with the top, tucked or not. I am 5’3″ and do have to be careful of the foot
wear with these pants or I look shorter and dumpy. Will have to remember some of these tips.
A lot to go through but really helpful.
I’m glad you enjoyed the post. Yes, it was a lot. But it’s hard to do a post like this and not leave gaping holes in the information if I don’t explain thoroughly. I have a feeling the information overload is going to save me some headaches here in the comment feed. ?
This is so helpful and timely! Just a few days ago I was struggling with what shoes to wear. I liked seeing all the little
ways you tweaked the same outfit. Blessed for My Day verse was exactly what I needed today. Thank you!
Wonderful. Thanks so much for reading and sharing your thoughts. ?
Hi Kay, I prayed for you this morning that your medical test goes well and that everything will come back good. Enjoy being with friends afterwards.
Thank you Nancy. ?
I really liked all the pictures and words talking about your thoughts behind each look. With my cold rainy weather I usually start my outfit from my shoes because there are days I need very supportive shoes or warmth of socks. Your post helped me see there are many ways to deal with changing up proportions! Thanks.
Hi Kristin. I often start with shoes, too. ❤️
Thank you for this informative post. The comparative photos really help to see the difference that small changes can make. I’m also petite, so the correct proportions are so important when putting together my outfits.
Yes! Thanks so much for reading and sharing your thoughts. ?
Hi Kay, this is such a great example of why I love your blog. This “how to” post is the ultimate in practicality. And I’m not really noticing about the light. Or hair or makeup. I’m too focused on comparing and contrasting the elements of style that you’re working with. Just yesterday I wanted to wear some green ankle jeans w my navy jacket and sweater, but couldn’t make it work (picture in our FB group). I need socks or tights or something for bare ankles and I can’t wear boots except for fleece-lined UGGS which are a totally different outdoorsy look. Reading your post, what would you think about creating the all-dark ankle/shoe look with navy loafers and tights? Or should I just wait for warmer weather? Sent w a prayer for your test.
Thank you for your post. I’m 5 feet and 4 inches and I am short waisted with longer legs. I cuff most of my jeans to ankle length, for booties. The majority are skinny or semi skinny. I also have a rectangle shape. What would you suggest for tops since tucking and crop tops are not the best for me?
Hi Beth. First I wouldn’t suggest high waisted jeans like these. So instead you could wear straight ankle jeans with more of a mid rise. Then you would probably be able to do a little front tuck, depending on the length of the jeans and your footwear, or just leave the sweater untucked. Of course, you’ll want to look at that and see if it works. I can’t judge that completely accurately without seeing you. But really ankle jeans should be your friend because they can help you balance that shorter torso.
Thank you so much for your help. I really appreciate all that you do!
You bet! ?
Kay—Hope all goes well with your tests. I really enjoyed this post because I rarely think of shoes first and never connected how my shirt affected the look with shoes. Very interesting. Enjoy your friends this afternoon and God bless.
Thank you. All went well. It’s all more of a nuisance than anything. I’m so glad you enjoyed the post. ?
Thank you Kay for a great post!!! I need to see more of these! I truly appreciate all your hard work and time you put into these posts! Have a Great day!
You’re quite welcome. I’m so pleased that it’s been so well received. Watch for more!
This was a great post. Proportion and scale are so important. As you point out, it can make or break an outfit, especially since most of us are not tall willowy models. The photos really show us the difference one little tweak can make. Love posts like this.
Great to hear. I’ll definitely try to do more. ?
??Praying for good report from your tests. I’m learning so much about contrast from your posts. Something I never noticed before,
I usually just tie my shirts or tops in front instead of tuck. I have no midriff but I do have long legs so I try to lengthen the top and I can control where I want the top to stop by doing this. Fabrics are so thin today that tying them is easy. I’m not happy about the thin part but theres a silver lining I guess. Of course this is a very casual look which fits my lifestyle.
That’s another great style hack, Eve. Thanks for sharing. I’m glad you enjoyed the post. ?
Excellent post! Thanks for breaking it all down. I appreciate your style tips and photos really help me see the big picture on achieving the correct proportions. Love the “buggy” story!
Glad you enjoyed the post, Jan. Thanks for letting me know. ?
Loved the Laura Petrie look comment! Yes, I can see that! Thank you for a very thorough explanation on the topic. The BFMD provided a great visual.
Thanks so much for, Terry. I’m glad you enjoyed the post. ?
WOW! What a fantastic post Kay! Thank you so much for doing the research and showing so many pictures that allow us to really see how to wear straight ankle length jeans while keeping our proportions in check.
I’m so glad you enjoyed the post, Ginger. Thanks for letting me know. ?
Great post. Enjoyed seeing how small changes made such a big difference. I too have struggled with straight jeans in the Winter. I still wear them but recently pulled out some old baby boot cut jeans (Lucky Jeans – Brooke style, mid-rise) and decided I liked the look a lot better than straight jeans. They really elongate the leg.