Styling Ankle or Crop Jeans for Early Fall

Welcome to Fall Denim Week 2024 at Dressed for My Day. I’m happy to say that cropped or ankle length jeans are still very on trend this year. Maybe you’ve already been wearing them this summer, in fact. As we transition into fall, these are my favorite jeans to reach for because they still feel cool, but they allow you to create all the autumnal blue jean outfits, too. Let’s talk about a few of the keys to styling ankle or crop jeans for early fall.

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The Ankle or Crop Jeans

Today I’ve created several outfits with three different pairs of ankle length jeans – two of them are wide leg jeans (but one is wider than the other) and one is a kick flare jean. I’ve grouped the two silhouettes together because generally you’ll wear the same kinds of shoes with them, but there are some differences in the tops and third pieces which I’ll explain further down in the post. All three of my jeans have a high rise because that’s what works best for me. But I’m linking you in shopping widget below to similar options with different rises. Note that all of these also come in petite sizes, and the Madewell jeans come in talls.

The Perfect Vintage wide leg crop jeans above are some of my favorites, and they’re available at a reasonable price from Madewell. I do size down to a 29 in these. I’m not sure if mine are the Altoona wash I’ve linked to, but they’re close at least. I purchased mine early last spring or maybe last fall, not sure. This Perfect Vintage has a leg opening of 18″, so it’s not as wide as the next jean. If you’re looking for a not-too-wide jean, this one may be your favorite.

I can just LIVE in the Paige Anessa raw hem wide leg crop jeans above. Constructed in a cotton blend, these jeans are super soft, but still feel and wear like traditional jeans on the body. They have nice stretch in them, but do not stretch out with wear. (By the way, the Madewell jeans above keep their shape nicely, too.) I wear a 31 in the Paige Anessa, and I can highly recommend these premium denim jeans. They have a 22 1/2″ leg opening, so significantly wider than the Madewell jean.

And for our third jean, I’m wearing the Mother The Hustler ankle fray hem jeans in Mint Condition wash (same jean, different wash). These are a kick flare or ankle flare jean, so they are a straight jean with just a bit of flare right above the ankle. You can get a similar jean in a mid rise in the Mother Rambler or this Mother The Outsider. Again, these are premium denim, so a little pricey. But if you wear your jeans often and for a while, price per wear will make this investment worthwhile. When it comes to denim, you truly do get what you pay for. By the way, Mother Denim is having a Labor Day Weekend Sale with up to 50% off select items.

That said, you can duplicate any of the looks I’m showing today with jeans from other brands. The point of this post is really about how to style the ankle length jeans, but I did want to share a little about the specific jeans I’m wearing in case you’re curious. Here’s a shopping widget with a wide assortment of jeans in similar silhouettes and ankle lengths.

How to Style Ankle Jeans for Early Fall

One of my favorite things about wearing ankle length jeans is that you can wear almost any shoe with them. They work great with traditional almond toe ballet flats or pointy toe flats. Below I’m wearing my Madewell jeans with my Paul Green leopard print ballet flats.

I think all silhouettes of ankle length jeans also look nice with loafers. For early fall and with this length of jean I’d suggest leaving off the socks. But of course you could also wear my favorite no-show socks if needed. They work great! (Sheec Socks is having a Labor Day Sale with 5% off +$35 | 10% off +$60 | 15% off +$75, plus they’re offering FREE shipping on order of $10+ TODAY ONLY.)

Above I’m wearing the Mother The Hustler ankle fray hem jeans (same jean, different wash) with my Gucci loafers, but the Sam Edelmans, shown below with the Paige Anessa wide leg ankle jeans, are so similar and even more comfortable. I think the darker loafer works nicely with this low contrast in intensity dark outfit above. But the flesh toned loafers work nicely, too. You’ll never go wrong with a shoe in your flesh tone because they basically make your foot disappear.

You can wear a heel with any silhouette of ankle length jeans, but I think they look best with the wider styles. A heel with a more slim fitted jean looks a little yesteryear, so a very small heel like this one from Talbots (not shown) would work better with the straight or kick flare jeans.

Above I’m wearing the Naturalizer kitten heel slingbacks with the Paige Anessa jeans and I think it looks really nice. You can also wear sneakers with ankle jeans; I just didn’t show any here. Let’s see, here’s a photo of me wearing sneakers with an ankle jean from a previous blog post. Those are actually the same Madewell jean, but in a different wash.

Bottom line, choose your shoes to reflect the vibe you want to create. You can use your footwear to create juxtaposition, wearing, for instance, a sneaker with ankle jeans and a blazer. Or you can keep the look consistent by wearing shoes that reflect the same vibe as your top. Let’s move on to what to tops to wear with ankle length jeans.

I actually took photos of another top and jacket with the kick flare jeans, but that outfit just didn’t work at all when I saw the pictures. So I didn’t have James process them. Now I wish I had one to show you so you could see the mistake. Bottomline, the neckline was a scoop neck and it was too low. So to create balanced proportions between your ankle jeans and the top, you want to make sure you wear a high enough neckline to give you “enough shirt” to balance the shortened pants. Make sense?

The top above works nicely because it has a reasonable neckline and it’s not too long. It’s not exactly cropped, but it does expose the zipper placket, which is desirable with ankle length jeans. This top creates good proportions with the ankle length kick flare jeans, but a fuller top would also balance the slim fit of the jeans.

Actually, the button-up shirt shown below would have created nice proportions with the slim fit jeans above. But it also works nicely for the Madewell Perfect Vintage ankle jeans because they’re not extremely full.

However, I would advise against wearing a very full and blousy shirt with wide leg jeans, especially if, like me, you’re not especially slender in the hips and thighs.

I do love a good blazer, and you absolutely can wear one with your ankle length jeans. You may remember that in Monday’s blog post on How to Style Straight Ankle Cuff Jeans I advised against wearing a long blazer because it would pull the look down visually (since the deep cuff already does that).

This is the blazer I had tried on with those jeans, and it just did not work. But this longline tailored stretch blazer worn over a sweater vest in the same fall berry color does work nicely with these darker wash wide leg ankle jeans.

Again, that cropped length sweater vest really helps to create those visually appealing proportions with the ankle length jeans. Yes, the neckline is low, but unlike the one in the photos I didn’t show (sorry about that), it shows enough through the jacket to work nicely. In the other photos I featured this bomber jacket (shown in this blog post) with the jeans. And that cropped length jacket worked really well, too. Basically I’d wear a slim fit jacket, like my blazer with the wider leg jeans and a fuller completer piece like the bomber jacket with the slim fit jeans.

Well, I apologize for not having photos of that outfit mishap. That would have been a good visual for “what not to wear.” But hopefully I explained the mistake well enough for you to know what to look for. If you have questions, just let me know. Remember, I’m just a gal getting dressed for my day. I’m not a stylist. I’m more of a researcher. So I’m sharing what I learn with you and still learning as I go!

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