Styling Crop Straight Jeans for Winter

I’m watching the trends evolve, and I’m here to tell you, the straight denim trend is finally hitting mainstream. What’s more, it’s here to stay for a while.

Of course, we should all wear what looks best on us, and I’m not kicking my skinnies to the curb, but I’m going to try to integrating this style into my outfits more as we head into spring.

I’ve been analyzing others who are wearing this style, and there are a few factors to help make crop straight jeans work for you.

#1. Proper Length is Key

Everyone is different, but at 5’5″, I personally need a 25″ or 26″ inseam. Any longer, and it looks like I’m wearing floods. My ankle-length skinnies are typically 27 or 28″, for reference.

It’s hard to find a 25″ inseam, but 26″ is pretty popular.

The Agolde mid rise straight jeans I’m wearing in this post have a 26″ inseam. They’re almost ankle-length on me, but I think they work. I just have to work a little harder to make sure my shoes work with them and not against them.

Also notice that my jeans are not super wide. Some girls can get away with that, but I like a slimmer fit. These have an 12″ leg opening, so not a whole lot wider than my skinnies, which usually are 10″.

Incidentally, these jeans are amazing! They are thick and super soft and hug the body in all the right places. Best of all, they have great shape retention and don’t bag out as you wear them. They’re TTS, or size up if in between; I have the 29.

#2. Choose the Right Shoe

As far as shoes are concerned, I like sock booties with crop jeans in the winter because you can wear heavy socks, and no skin is exposed.

Sock booties have a high shaft and fit very close to the foot, so they keep the ankle area slender, which helps offset the extra width of the straight-cut jeans.

A pointed toe also helps keep you looking long and lean as well.

Style Tip: Your jeans should extend over the sock booties by at least an inch, so when you sit, you still get good coverage.

I recently purchased these Jeffrey Campbell Siren booties, and I love them. They have a padded footbed, and the neoprene material is super soft against the rest of the foot as well, and the shaft is soft and flexible too so they don’t rub you raw if you aren’t wearing tall socks.

These have a 3.5″ heel, but I find them very comfortable. Here’s a lower heel option, and a budget option.

You can also wear a more traditional bootie with a mid-height shaft, and in this case, they look best when the jeans just barely meet the top of the boot, but don’t “buckle”. That means, you may need an even shorter inseam, or you’ll need to cuff.

I recently ordered these Goodthreads crop straight jeans from Amazon, and they have a shorter inseam than the Agolde, even though it says 26″ online.

They work pretty well with my Marc Fisher Chelsea boots, whereas the Agolde are a little too long for them.

This is the Agolde…see how the jeans get caught on the back of the boot? (They do this on the front too.)

And here’s the Goodthreads jeans with the same boots…they just barely meet the top of the boot. This is a much better combination.

Another shoe that I like with straight crop jeans is a loafer mule.

These work because they expose a few inches of skin at the ankle, which is also slimming, and they usually have more of a pointed toe, which helps elongate the line of the leg.

Of course, if it is super cold where you are, you may have to wait a few months to wear this look, but I wanted to show a non-boot option.

Regular loafers work too, but I find the mule more feminine somehow, and a little more fashion-forward. I know some of you don’t like them, but if you do, they’re a great option, especially as we head into spring.

You can do a sneaker for a more casual look, just make sure the jeans are short enough to expose a few inches of skin in the ankle area. I like the length of the Goodthreads with sneakers.

#3. Your Top Matters

Your top is the other crucial piece to the puzzle when wearing crop jeans. Most people talk about what shoes to wear with crop jeans, but I rarely see them address the top!

I think this has been the most frustrating part of the crop jeans trend for me. I can’t just throw on any sweater in my closet with them and have it look right. Here’s why:

You are shortening the line of the leg by wearing shorter pants, so to keep a proper balance (1/3 to 2/3 is ideal) you have to also shorten your top.

This means tucked in, or at least a front-tuck.

The sweater I’m wearing here is already on the shorter side, and it fits fairly close to the body, but I still gave it a front-tuck. It helps that it is a thinner knit as well. (Unfortunately, it’s old and no longer linkable, but this is why sweater styles are getting shorter.)

If you’re busty, like me, tucking isn’t always the best look, so it takes a lot of trial and error to find the right combination of tops, jeans, and footwear to make it work.

Funny thing, though. When skinny jeans started to get popular, I felt the same way about them. It will get easier the more we play around with this silhouette.

I completed the look by adding my black leather jacket.

This is also an older piece, and therefore unlink-able, but I really like the front center zip as opposed to the asymmetrical zip and large lapels that is common with so many moto style jackets.

Not that I never wear that style, but it’s hard to find ones that don’t make me look top-heavy. This one is a good option (same brand as mine, butter soft leather!) And I like the looks of this one and this one as well.

Finally, I added a belt and a red bag to complete the look.

I really love this outfit, what do you think?

Styling Straight Crop Jeans

I played around with both the Agolde and Goodthreads cropped straight jeans one afternoon this week, and here are some more outfits I came up with…

Here’s one that does NOT work. The shoes are great, but the sweater is too long, and it’s awkward front-tucked with the split hem.

This sweater is a thinner knit, and it’s a little on the cropped side, and I feel like it works. Unfortunately, it’s sold out.

I like it even better with a front-tuck, but it could use a belt.

This one works okay too, with the Siren booties and Naadam scoop sweater. (This sweater finally went on sale! I’m wearing a small.)

This is another sold-out sweater, but because it’s cropped, it works really well with the same jeans and boots.

And this is cute too, with the loafer mules and my Everlane varsity cardigan.

See how the shorter sweaters in the thinner knits keep the overall look balanced?

Here’s me trying the look we photographed above… sometimes I think it’s nice to see the mirror selfie as well.

And then I tried a silky tank top with a leather jacket on top. I like this for date night!

Taking it more casual, this hooded sweater is cropped and boxy, which works with the jeans, and I added my white Vejas.

This look would be better if the jeans were an inch shorter, so I tried a cuff, and I also gave the sweater a front-tuck.

Here’s another casual look, with different sneakers and a sweatshirt that’s on the thinner side.


And un-cuffed…

And then I have a couple with the Goodthreads jeans.

I ordered two colors — the darker pair is the 28, and the lighter pair is the 29. The 29 is more comfortable, but the 28 fits, and if they bag out any, it might be the better choice. I still need to wear them around the house and see how they do.

This sweater (more sizes here) is on the chunkier side, but I happened to have it on already, so I tried it first with the darker wash jeans and loafer mules. I like it!

And here are a few more shots of the striped hoodie with the light wash Goodthreads jeans.

As an aside, this hoodie is AMAZING, you guys. Super soft inside and out, a nice substantial fabric — not super thick, but not thin either — and the fit is cute too. Very good quality for Amazon, and I’m definitely keeping it!

I love this look for casual weekend outdoor events in the springtime.

I realize I’m breaking my own rule here with a longer top, but because everything is light — the light grey/white top, light jeans, light shoes (and my winter-white skin, haha!) there is nothing to break up the look, and I think it works fine.

Shop the Post:

For the Pinners:

Showing you how to style straight crop jeans for winter with boots, mules, and sneakers. Lots of outfit ideas!

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photos: Alison Cornell

Join the Conversation

82 thoughts on “Styling Crop Straight Jeans for Winter

  1. Love these looks but we older gals have backsides that don’t look so great in jeans. At least with skinny jeans and longer tops there is some coverage. Suggestions?

    1. I’m not a fan of straight crop jeans with longer tops, because the tops are rarely fitted, so you have a wide, straight top on top of wide, straight pants, and there is nothing to define the waist. That said, some people do wear them. Amy Ann looks really cute with a tunic and straight crop jeans in this post, but she is very tall and thin. Also note, the heels help:

  2. Great post.  You nailed it!  I love these looks and appreciate the examples of what not to wear.  Do the Aquatalia booties work with these jeans?  I just got them…a spurge for me and they are gorgeous.  Not sure if I’m keeping them – how much I’ll wear them.  

  3. I absolutely love those jeans – they look amazing on you and this is the type of outfit I would wear.  Love those Jeffrey Campbell boots – I have them in the camouflage from a couple of years ago and I wear them all the time (except in snow!)  

    I know that you are off to Paris in the springtime – I just wanted to share with you an Instagram person I follow from Paris – she is  That is her blog but she has Instagram as well.  I can’t understand a word of it, as it’s all french but her pics are beautiful (her Paris apartment is to die for) and her style is amazing.

  4. Thank you for posting this today because I have two pair of crop straight jeans that are going to the resale shop tomorrow. First, I purchased both on sale and second, I am short so maybe that’s why I could never made them work. But seeing how you styled them again is very helpful. I didn’t realize that is was okay for them to flare out a bit on the sides so I would cuff them, but still didn’t think they looked right. They are both very comfy jeans, as one is Paige and the other from Anthropologie so I hated to part with them but I just haven’t torn them at all. Maybe their just not a trend for petites and I almost think they’re too much work to try and style. But I do like them best with mules on you and may give them a second chance? 

    1. I’d rather them not flare, but these do from certain angles. It’s okay, but definitely not as easy to cuff. You could also chop them off if they’re not the right length — at least try it before donating.

    2. I’m 5’1” and I’ve tried them several times.  When I see them on me, I quickly say “NO!”, but not without laughing first!

  5. Loved this post. I just received my Agolde jeans yesterday and was trying to decide if I was going to keep them. Seeing you try them on with different sweaters and shoe options helped me to decide to keep them and try this look. 

  6. This is a really helpful post! It’s going to take a while to transition my tops to shorter lengths and to get used to my hips being exposed. It’s so hard to find the perfect length an not emphasize wider hips. What size did you order in the striped Amazon sweater? I’d like to try that one as I find I wear my cropped jeans more casually so that would be perfect. Plus my daughter bought me some vans for Christmas so they would work together.

  7. I agree. I cannot find a shorter top or boxy top (whatever one calls it) that looks good on me with my waist (or lack thereof these days) and a larger bust. The super high jeans are not comfortable, and I don’t like that look. I am wearing higher waisted jeans which are good, but not the super high. Without super high, if I move, my sweater goes up too high if I am reaching. (I teach and am always writing on the board.) I am still working on the front tuck, but I haven’t gotten that right yet. Then I go back to my favorite skinnies or leggings with longer tops. So frustrating!

    1. Ultimately, everyone should wear what they feel best in and what works for their body. This is what I’ve figured out works for me, and I do have more of an hourglass shape (for now, lol! Menopause is looming.)

  8. Personally, the sock bootie with cropped jeans is not my favorite look. I think because it reminds me of when my kids were young and would quickly outgrow their jeans. It looked like they were ready for a flood. I gravitate to the mules and sneakers with the cropped jean. I even like your look in the tan (too long) sweater and mules. I think it looks more slimming than some of the other examples. (At least in these pictures….and not that you don’t look slim in all the examples! You do!)

    Overall it seems like a lot of work (finding the right jean length, top fit, and shoes) for such a simple – almost forgettable – look. I guess I am just a late adopter if this specific trend. I was when skinny jean became the new style too, but now I love them! Lol.

    I really like the Amazon hoodie.  I usually wear a small or medium in tops but am a bit top heavy. What size worked for you?

    As always, thanks for all the time you invest in educating all of your readers!!!!

    1. I hear ya on it being a lot of work, but I remember feeling this way about skinnies at the time. I sort of gave up on them for a while, but now that tops are getting shorter, I’m finding them easier to work with.

    2. Ashley – I feel the same. I can’t help but feel every time I see someone wearing them, that their pants must have shrunk, because they are too short, lol. And I have a feeling anyone who’s not up on the latest fashion trends (basically most people in my life) would think the same thing if I were to wear them.

  9. Great post! So many useful pieces of information.
    Loving the gray sweatshirt, please tell us what size your ordered.


  10. I love this look! A nice change from skinnies. I especially love the look with sneakers or loafers. But I dress more casual on a daily basis. Man, another hoodie to love! To buy or not?? Have you worn the jeans from Amazon long enough to know if they bag out yet? I’m interested in buying since I don’t like to spend a lot on jeans in general. Thanks!! 

      1. Aww, that’s sweet. Thanks! But I already ordered them! And the hoodie. And the cardigan you showed on IG. 😬😂

  11. Loved all the looks today. Lol, I just tossed a pair of jeans like these into my donate stack because I couldn’t figure out how to style them and make them look good. Thanks for the outfit ideas. Now I’m going to pull them out of the donate stack.
    Have a wonderful weekend!

    1. Loved the post, so helpful!
      Heading to Disneyworld in 2 weeks and the Amazon hoodie will be perfect…plus I got an Amazon gift card for Christmas, time to spend it!

  12. I have to agree with the other ladies, I don’t love the shorter sweaters in the pics as they seem to emphasize the larger part of your body and at least in the photos you look heavier than usual. I’m not trying to be critical but just not sure of the look. I do agree that the striped hoodie with the sneakers looks great and perhaps it’s because it’s just a bit longer but the color is soft and the sneakers again are soft in color so that the whole look seems to flow and you look amazing.. 
    I too would love to know how that hoodie runs as I am going to order and also the sneakers with the gold…
    Thanks Jolynne you do all of the hard work for us😊

    1. I don’t think anyone looks as thin in straight jeans as they do in skinnies… or even bootcuts, for some reason. It’s a different silhouette, for sure. But I like the way the shorter tops look – I like that you can see the curve of my hips. It’s interesting to see how different people see the same looks differently. 🙂

      The sweatshirt is a small.

  13. Great post! Thanks for explaining why the top needs to be a little shorter when you wear cropped pants. Love those sock booties! I need a new pair of black boots, so may invest in the sock booties. 🙂

  14. To my eyes I like the outfits with the Agolde Jeans (uncuffed) best.  The shorter Goodthreads jeans or the cuffed Agolde make my eyes see dumpy ( and I know there is no dumpiness in you at all).  I love shorter sweaters, but my legs are petite so I haven’t been comfortable trying this jean style.  But it looks good on you (in my humble opinion mainly with the slightly longer crop length jeans).   Will pass on the jeans but looking forward to seeing more shorter tops as you style this look.  

  15. I really liked this post.  You gave some great ideas and tips and several good examples.  Unfortunately, being only 5’1” it is hard to find jeans that hits the right length unless you get them hemmed. I thought this style looks really good on you.  Really enjoy reading your daily posts! 

  16. I guess I should begin the hunt for cropped straight jeans. When my favourite blogger caves so must I. 😉

    1) Jeans must be short enough to look intentional and a narrow leg opening
    2) shorter top
    3) right footwear 

  17. Thanks for your hard work on this informative post. I like the look but I’m not going to try it until the weather warms as I don’t want to buy another bootie and all my sweaters are longer. I love the casual vibe looks the best of all and can’t wait to play with this look once Spring arrives. 

  18. I know I’m an outlier but I’ve never been fond of skinny jeans and the oversized top look. Love the “slimmer” look, especially the tops on you!

  19. You nailed it!  Love this post. (Haven’t commented in ages.  Maybe since you were still “Musings…?”) Have you done one of these with flares/bootcut jeans?  I tried on a pair recently and loved how they made my legs look.  However, I hit pause on buying them when I realized I wasn’t sure what shoes to wear with them.  Or maybe, it was that most of my shoes won’t work with boot cuts!  

    1. Hey Lizz, booties with any height heel look amazing with bootcut jeans. The key is that the hem has to fall about a half inch from the ground to look right…you don’t want to have floods or your hem dragging on the ground. Once you find the right heel height and inseam, bootcuts are the most flattering jeans for giving your curves balance. 

  20. Great post and a lot to consider. I really like the first style with the leather jacket, and the other options look good too. I don’t know but I kind of like the sweaters without the front tuck?? I have been looking to replace my crop jeans but issue is I’m 5’3 and they are usually a normal length on me so I need to look for shorter so that they hit above my ankle. I like mine with a wedge but I’m not opposed to the mule and sneaker either. Great tips to remember… Thanks and I do love that hoodie..

  21. Have you tried the AG Isabelle high waist crop straight yet? I’ve been scoping them out as an option since I love AG Farrah’s.

  22. Great post! Thanks for all your hard work getting it together.   I like the idea of the slimmer straight crops like you have.  I do have some slimmer straight jeans that I’m thinking about cutting off.  Are the raw hems still going to be in?  I’m so short that I have to hem everything and would love to be able to just cut some off myself.  I do love how they look with the mules or sneakers, with some ankle showing.  

        1. I have no idea why it lost my punctuation and space, but that was supposed to be “Good to know!  I will try cutting mine.”  😂

  23. I love this style…but you pretty much confirmed what I’ve been finding. I don’t think I’m going to be able to pull it off. I’m 5’3″ and I just can’t find a short enough inseam (unless I take the scissors to a pair) I’ll keep looking, but don’t have much hope. Come on retailers, us short girls want in on the trends too😉

  24. Thanks for the great post! Let us know what you think of the Amazon jeans. I’d rather try a lower price to see if I like the style. 

  25. Great post! Which of the 2 brands of jeans come up higher? I need a pair that help reign in the muffin top. Thank you!

  26. I actually think that you could have gone down a size in the agolde jeans, depending on the comfort. I like the look with the cropped sweaters and the cropped jeans. I really love the Gray cashmere sweater look too!  

    I really need to do a closet purge of my sweaters. I need to get rid of the high/low hem sweaters because they will never work with the new cropped silhouettes that we are seeing. Plus, I just don’t reach for them any more. 

  27. What a great post!!! Thank you for your time and effort! I absolutely LOVE the straight crop look. In fact I just ordered a pair of sock booties (per your suggestion); I can’t wait to try them out!
    (BTW-Would love to learn more re the Rule if Thirds (specifically when wearing long cardigans:blazers).  Happy Friday!

  28. Such a helpful post!  Now I know why I didn’t like my straight legged jeans when I put them on.  Thank you bunches!  Shorter tops and a front tuck makes all the difference in the world.  Hope you have had a great day!

  29. Hello, 
    Thank you for the tips on styling shorter length straight leg jeans. 
    How do you style a full length straight leg jeans or pants?   What shoes and tops ?  
    Thank you, 

  30. I love these jeans  on you, Jo-Lynne!  I do have one pair of straight crop jeans, but due to the color and my foot ware I’ll most likely wear mine this Spring and summer.  ( I know you mentioned wearing these jeans in the Spring. ) 
    I love the way you paired them with the shorter sweaters and those gorg booties.  I’m not a fan of jeans and long, tunic type tops and sweater…. I took your advice and took selfies of myself in tunics and they make me look frumpy. 
    As for the Goodthread jeans…. I think you look fabulous in the dark wash jeans. They look like they fit you better. However, only you will know after wearing them for a few hours.  Wonderful, information post! Thank you!! 

  31. Love the striped sweatshirt, light jeans, and sneaker look! How is the sizing on the sweatshirt? I looked but didn’t see if you mentioned what size you are wearing. Thanks!

  32. I agree with the not short top/tummy thing…..and I already ordered the Amazon sweatshirt! 
    Appreciate this post Jo-Lynne!

  33. Ugh!!!!!  I hate the thought of these knocking the skinnies out of style. I’m 5’3” and the crop isn’t going to look right on me and like you said the length of sweater will have to change. They look good on you but I still like skinnies on you the best. 

  34. I love that the straight leg jean adds a new, different silhouette for days when I’m getting bored of skinny jeans! I usually like to reach for them on slightly milder winter days when I can wear a bootie, show some ankle, and pair it with a wool coat (rather than a heavy parka). I feel like it breaks up the monotony of winter outfits! Great post!!

  35. I saw a lady in TJMaxx that looked to be mid-60’s wearing a pair of light colored cropped flares. She had on a black light weight sweater-cape over a long-sleeved white top, and black flat mules. She looked so very stylish and put together!

  36. This is such a good, informative post.  Thanks for all the different looks with explanations.  I love the tip of just cutting our jeans to fit our needed length.  You mentioned that last spring/summer and I’ve been cutting ever since!  Haha, it works!

  37. Hi, Jo-Lynne!  Thank you so much for an awesome post.  I really appreciate you explaining WHY something doesn’t work in terms of the proportions of tops/hems/shoes/boots/cuffing. That is a huge help.

    While I will be clutching my bootcut jeans to the bitter end (and still don’t like this look,) I think you did a masterful job of finding the best of them that fits you well and is styled nicely.  

    Now, what kind of summer shoes/shooties/booties do you think works?  The lower sneaker and mules look good, but what about summer/spring transition with the shooties?  I am curious how the new lengths will work in that scenario.  So expensive to try to keep up!  The shoes are what force me to adopt the new looks.  At a certain point, there are no older shoes that match the trendier pants, IMO.  You have to change the shaft height and heel thickness/height to get the proportions right for the pants.  Ugh.

    1. I think we’re going to see everything with them – sandals, wedges, slides, etc. Our eyes will adjust, and they’re not going to look so off. Of course, fashion always tweaks things a bit, so it’s hard to say what we will see most. I do think the shield sandals will work with them tho – they read so much like a bootie.

  38. Thank-you! Very helpful post since I like straight jeans with the shorter sweaters. Thanks for all your hard work trying on all those clothes and now I don’t have to! 🙂

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