Fall/Winter Fashion
49 Comments

How to Wear Straight Cropped Jeans This Fall

First of all, no hate mail please. Yes, I am posting a decidedly fall outfit in July. I know, I am even annoyed with myself. But y’all. When these pictures came back, I was so excited to share them with you, and we all know these pieces may be gone by fall. Plus, it gives me the perfect opportunity to address a topic I’ve been wanting to write about — how to wear straight cropped jeans and not look like a clown.

Jo-Lynne Shane showing how to wear straight cropped jeans this fall with ankle boots and a cropped colorblock sweater from the Nordstrom Anniversary Sale.

These are all #NSale purchases, naturally. This mock neck colorblock sweater is such a fun little piece for fall. The quality isn’t superb, but at $31.90, I can’t complain. For size reference, I’m wearing the small.

This black/brown combo is low inventory, but it also comes in a really pretty red combo that isn’t quite as fall-ish but it’s really pretty. It also comes in plus sizes, by the way, and they are fully stocked in this color.

These jeans are the Frame Le Slender Straight Leg Jeans. Even on sale, they’re pricey, but this is the first pair of straight cropped jeans I’ve tried that I even remotely liked on myself so I decided they were worth the splurge.

I love the lightly faded wash, and they’re super soft and comfortable, plus they have a trendy high rise.

Jo-Lynne Shane showing how to wear straight cropped jeans this fall with ankle boots and a cropped colorblock sweater from the Nordstrom Anniversary Sale.

At first, I wasn’t sure I liked them paired with these booties, but the sales associate I was working with assured me that it works. I do like how you can see the buckle detail, and when I sit and move around, that’s even more visible.

I am beyond shocked that these booties are still available. I absolutely love this caramel color for fall, and the way it pairs with the light blue denim of these jeans is fantastic. They’re by Sam Edelman, so they’re good quality and comfortable, and priced just under $100 for the duration of the Anniversary Sale.

So why does this outfit work? To be honest, I am still figuring this all out for myself, but I’ll take a stab at it. For one thing, these jeans have a “slender straight” fit, which works better for my frame. Because I’m hippy but have thin legs, pants that are more fitted (i.e. skinnies and legging jeans) draw attention to where my legs are the thinnest, so the slender cut of this straight leg style fits me better than wider leg styles.

The light neutral color of the booties along with the light wash jeans helps lengthen the leg line and not look as cut-off where the jeans end. It’s okay that the jeans extend over the booties by about an inch because they hang nicely and don’t get caught on them.

Typically I’m seeing more sock booties with this style of jean, but these seem to work well too, which is great because they’re a more versatile style than the sock bootie.

Jo-Lynne Shane showing how to wear straight cropped jeans this fall with ankle boots and a cropped colorblock sweater from the Nordstrom Anniversary Sale.

The other component of this outfit that is super important is the sweater on top. I tried a few different tops with the help of my sales associate at Nordstrom, and the ones that worked best were the shorter, boxier styles.

I know, it seems counter-intuitive, doesn’t it? I’ve also seen a lot of women tucking tops into this style of jeans, but that is simply not an option for me, as I’m very short-waisted plus also busty — not a good tuck-in combination! I can’t tell you how many sales associates have tried to get me to tuck in (or belt) a top, and when I do, they agree — it just doesn’t work on me.

But a boxy sweater in a shorter (but not cropped) length seems to do the trick. It’s 22″, by the way. I also liked this sweater, this one, and this one with these jeans.

I’m obsessed with the Vince one; the picture on the website does NOT do it justice. You can see how it looked on me with these jeans in this post. It’s longer than the others, but it still seems to work due to the boxy styling, I guess?

Jo-Lynne Shane showing how to wear straight cropped jeans this fall with ankle boots and a cropped colorblock sweater from the Nordstrom Anniversary Sale.

sweater (also in plus size) // jeans // booties // bag // earrings

photo credit: Alison Cornell

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49 thoughts on “How to Wear Straight Cropped Jeans This Fall

  1. Why are cropped straights so hard to wear but no one seems to have a problem with cropped skinnies?  Wouldn’t they both cut the leg in the same place?

    1. I think it’s because the cropped skinny follows the line of the leg and creates a more natural silhouette, where the cropped straight hangs straight from the hips (the widest area of most women’s bodies) and then just chops straight off, shortening the leg and creating a rectangular silhouette — not what we are typically going for. That’s how it reads to me… but I am no expert. I’m trying to figure it out with the rest of you! LOL!

  2. Love the jeans and this is a great fall look.  I would also love to see how you would wear the straight cropped jeans on a cool summmer evening or early in the fall because it seems like they could be a great transition piece.  

  3. I love this outfit on you!! Perfect for fall!

    I ordered the booties, love them but they seem a little snug – not sure if it’s our hot and humid weather. I am usually a 7 without fail in SE. I ordered a 7.5 to try. The blue/gray color is so pretty too. Not sure I need two of the same bootie though!

    I also love those jeans, wish they came in petite! The Caslon ones I had my eye on sold out in my size, will have to see if they restock on Friday for public access. The sweater sold out in my size too, darn! 

    I can’t wait to see more fall fashion from you. I do love summer but fall is my favorite. 

  4. So…if you had to predict…is this cropped/straight style jean THE big thing for fall or just A big thing….i.e., will your AG skinnies still be your go-to jean… but these are a nice change?  
    I was kind of liking the cigarette legged versions I’ve seen…still have a nice slim leg.

    Seeing your outfit (and my fab red loafers that arrived yesterday) makes me less sad about fall 🙂  #love summer.  

  5. Love this post! It’s fun to look ahead to fall fashion while still enjoying summer ( the photo session was probably brutal though, so thanks for suffering through the heat for us 😁).
    I think this is a very grown up way to wear a trend I see a lot of teens in our youth group wearing. I am excited to try this out.. in October lol

  6. I love this look for Fall which happens to be my favorite season here in Virginia! I may have to add a pair of straight leg cropped  jeans to wear with booties. 

  7. Well, I’m more of a cool weather person so ready for this but not where I live til Oct. So happy for you & your new home. Have you posted since you moved in?

  8. Great news on your 3 children and the dog playing in the pool together!  That had to make your heart feel so good.  Have fun organizing your pantry today!  That task can be a bit overwhelming, but fun at the same time.  Now to the outfit.  Because I LOVE fall, I’m thrilled to see you in a fall outfit.  I really like the straight legged jeans and want to try a pair.  Because booties and I don’t work well together, for numerous reasons, I am wondering what other styles of footwear I can wear to look put together.  I’m sort of thinking a non-chunky pair of mules or slides would work, but I am not having luck finding them with arch support.  We are happy to be in the NC mountains, out of the heat and humidity for a few days.  Have a great day!

  9. I enjoy seeing how you put outfits together!  My shape is different than yours but I can learn from your process of how things look.  I am pear shape, I think, and so really long sweaters and tops don’t flatter me.  I also like the color of those booties!  But my heart was a flutter when I saw that Brahmin bag, love ❤️ the color!  I have a few Brahmins and I love them all!  Thank you for your insight!

  10. Love, love, love this sweater. I noticed it right away. Those boots are pretty awesome too. Over the next few weeks we are doing another house/garage purge and I think I can make room for these two items on my fall list! 🙂

  11. This outfit knocks it out of the ballparks! Love the cropped pants styled with a boxy sweater and I much prefer booties like those versus the sock ones.
    I know it’s hot out but my mind always turns to fall clothes by the end of July. I love seeing what is going to be ” in” for A/W 2018. 

  12. This outfit is cute and cozy looking! So I’m very curious about these jeans. I’m tall though (5’9”) so the length is going to hit me above my ankle. What kind of shoes will work with that? If I wore low booties I’d feel slightly dorky 😬. I’m used to above- the-ankle skinnies that I could wear ballet flats with but this is unfamiliar territory! What do you think?

    1. It’s totally trial and error for me at this point. I don’t feel like I can give advice without seeing the exact combination of pieces. They really are tricky. I’m going to say mules or loafers are your best bet.

  13. Cute outfit!  As much as I love Summer, and it is
     just getting started up here, I do love Fall clothes! Sweaters and boots are my favorites.

  14. You wear this outfit so well and your description why makes sense to someone who identifies with the same body type.  Love all of it!

  15. I love this look on you so much Jo-Lynne that I’m tempted to try it. I have been in love with skinnies since the style came in and only own a pair of girlfriend jeans. Wondering how these would look with Chelsea boots. Due to a back injury, I struggle to wear my closet full of amazing heeled boots and shoes and have found Chelsea boots to be fashionable and fit my style. Don’t get me wrong, I still wear my heels, lol. Just not for every day now. What do you think?

  16. This sweater looks soooo good on you…much better than on the N website! Hoping they restock when the sale goes public on the 20th! Can you show us how to wear skinnies with this type of boot? Can you still tuck skinnies into booties? I have ample hips, but even skinnies are a little loose on my calves, so I don’t think I want to go with the straight leg style.

    1. Yeah, it depends on the length of the jeans, I guess, and how tight they fit to the ankle. I may cuff my ankle skinny jeans with these booties. I’ll have to play with them, since the shaft is higher than some.

      1. I almost always have to roll my skinnies, as 1 I’m short and the other reason is my dark wash skinnies fade blue on the suede booties. I hate that. I am careful and it happens. I wish they’d put our more taupe leather booties. They seem to always be suede.  

  17. Regarding crop jeans: where do you recommend they end? How much above the ankle bone? ( I am in AYW Academy, BTW ) I tried wearing booties with cropped skinnies last fall/winter, and I thought I looked like a total goober. I think I look better in them with flats or sandals. I am anxious to try some straight crops, because I think I can pull it off better than the skinnies, though I still don’t think the booties will look right. Something about that break between the hem and the booties…I just can’t get past it! And I have a cute pair of Lucky Brand booties in black, and now I don’t know what to wear them with. 🙁

    1. Crop is sort of a nebulous term. Basically they can end anywhere between the middle of the calf to the ankle, but I consider them shorter than ankle pants and longer than capris, so maybe an inch or two above the ankle bone. As you know from AYW, a lot of it depends on body type, as well as the shoes you’re wearing with them. I like my cropped skinnies with flat sandals and wedge sandals. I do wear them with certain booties, but more often I tuck them into my knee-high and OTK boots in the winter.

  18. I remember when all I wore was straight leg, and never skinny jeans. Then I branched out and tried the skinny jean and fell in love with them, and felt over all they were more flattering for my figure. Now I try the straight and I feel funny in them. You’ve styled these really nicely though and I do love the pop that purse gives to your outfit.

  19. This is about the best I’ve seen straight crop jeans look.  I like the wash of them.  Great job.  But……you know if you fashion bloggers keep styling and looking good in them, they will take away our skinnies. LOL  Have fun organizing.   

  20. You nailed this look! I had pretty much ruled out this type of pant/jean but after seeing how you styled this outfit (and explained it), I think I might be able to pull it off. Love the booties and I am so glad that you brought that handbag home with you! How wonderful that all 3 children and the dog were enjoying the pool.

  21. I’m enjoying seeing all the new fall looks, so no hating from me! I’m glad you finally found a pair you like, and I think they look great on you -especially paired with the other pieces. I have two similar styles coming my way this week. I’ve been debating on trying this style so we’ll see!

  22. Jo-Lynne 
    So happy you addressed this jean question! I literally tried on this style today to pack for a trip out west and got out my booties and could not decide. It is the top that does it! Where I am headed there will be fall clothes in Aug and Sept so I greatly appreciate any fall info. Those boots you styled are really cute! Thanks! 

  23. Thank you for the break in summer fashion! Love me some fall clothes and this outfit is great on you. I can see the sweater with some lightly distressed black jeans too. Can’t wait to see the line-up of fall fashion posts!

  24. I’m actually excited to start shopping for fall stuff!  I’m tired of the hot weather!  Besides like you said,  by the time it feels like fall (November here in Mississippi!) all the good stuff will be gone!  Btw love that you combine black and brown, that’s one of my fave fashion rules to break!  Same with pink and red!  
    On a completely unrelated note, I was thinking the other day about your “fight the frump” series!  I really enjoyed those articles and would love to see more!  Have you thought about doing one on makeup?  I know a lot of women (myself included) know their makeup lpokd frumpy but are clueless how to improve it.  Just an idea! 
    Keep the fun fall posts coming!  Especially outfits that can transition from now til fall! 

  25. Great purse!  I really  like Brahmin bags.i have one that reads brown to black and goes with everything. The cool texture in the leather is so much more interesting to me than many popular bags where the most interesting thing about them is the label/logo. 

  26. I think this outfit looks great on you! The proportions are right. It is a tricky look to pull off – the cropped straight leg jeans w/ankle boots ot booties. I wouldn’t be able to do it. I have shorter legs and a longer torso, smaller on top. I’d be ready for the circus for sure. 🙁

  27. These straight leg jeans actually look very good. It’s the first pair I can say that about. The whole outfit is lovely. I’m glad you’re enjoying your Brahmin bag. I’ve been a fan for years. My Mother’s day gift was the small Lena tote. The dimensions are nearly the same as this bag and I agree that it is an ideal size. Mine is Pumice which is a cooler beige. I find it goes with everything and I find myself ignoring all of my other bags.

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