Fall/Winter Fashion
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How To Wear Crop Flare Jeans with Boots This Fall

As the denim debates rage on and straighter styles become more mainstream, I’ve been getting a lot of questions about how to wear crop flare jeans with boots this fall.

How To Wear Crop Flare Jeans with Boots for Fall 2021

I think we can all agree that straight ankle jeans and crop flares pair easily with sandals and sneakers for summertime, but how are these styles going to work with boots when cooler weather comes along in a few months?

I was super excited to see the Mother Insiders, my favorite style of crop flares, pop up at the Nordstrom Anniversary Sale! Light washes are trending right now, and this one is perfection.

Unfortunately, these jeans are low inventory at the moment, but here are the Mother Insiders in other colors and washes, and here are some more crop flares at Nordstrom. Also, the Madewell Demi Boot is a good option, and a lot of those are on sale right now!

How To Wear Crop Flare Jeans with Boots for Fall boots // jeans (option/option) // t-shirt // cardigan

These jeans also have ripped knees and step hems with frayed edges, so they’re definitely on the more side, but I’ve actually been impressed by how versatile they are. I styled them into another outfit with a fine-gauge short-sleeve sweater and heeled sandals, for an interesting juxtaposition, so stay tuned for that! But back to the question at hand…

How do you wear crop flare jeans with boots for fall???

Well, as it turns out, it’s not as difficult as we all may have feared. These jeans happen to pair perfectly with the Vince Camuto Welland Booties, also from the #NSale.

This combo works because the jeans just touch the top of the boot in the front, but they don’t buckle or lose their silhouette. In my perfect world, these jeans would be a half inch or so shorter, so there’s about an inch of skin showing between the hem of the jeans and the top of the boot, but it’s not a deal breaker.

Mother Insider Crop Flare Jeans with Vince Camuto Welland Booties from Nordstrom Anniversary Sale 2021

It also helps that these booties do not have a tab on the back. I realized that, as I tried these jeans on with some of the other boots I brought home from the #NSale.

Take a look at the same outfit with the Marc Fisher Gadri Booties. They’re a similar style to the Vince Camuto Welland Booties, and both are a great deal at just under $100. But the Marc Fisher has a slightly higher shaft, plus that tab in the back, which catches the jeans when I move around.

boots // jeans (option/option) // t-shirt // cardigan

The stylist who was helping me at Nordstrom last week said that wouldn’t bother her, but it’s not ideal. If you are taller (I’m 5’5″) or your jeans are an inch shorter, they’ll look better.

I also tried these jeans with a few of the higher shaft Chelsea boots.

The Louise Et Cie Varsan Platform Chelsea Boot is very comfortable in spite of the heel. It has a 6 1/2″ shaft, which is plenty tall to wear under these jeans, without risking the jeans getting caught up on it when you move around. These will come in handy when it gets colder, and I don’t want to bare my ankles.

boots // jeans (option/option) // t-shirt // jacket

But I like the Tory Burch Chelsea Lug Bootie even better with these crop flares because it has a slightly taller heel and an even slimmer shaft, for a more flattering silhouette. Either work, it just depends on the look you’re going for.

boots // jeans (option/option) // t-shirt // jacket

Finally, I tried these jeans on with the lower-heeled Vagabond Marja Cap Toe Bootie. These booties may look stiff, but they’e extremely comfortable. I highly recommend them for anyone with finicky feet. This bootie also has a 5″ slim shaft, so the jeans easily slide over top. (Size up in between.)

boots // jeans (option/option) // t-shirt //  jacket

All of these looks work because the jeans either skim over the top of the boot, or the hem ends just above the shaft of the boot. (Even the white Marc Fisher boots are okay, but they’ll work better on taller girls, or with a slightly shorter pair of jeans.)

In the case of the featured outfit, I like how the light wash denim creates low contrast with the camel color of the boot. That way, you don’t visually chop up the line of the leg.

Mother Insider Crop Flare Jeans with Vince Camuto Welland Booties and Tory Burch Carson Striped Crossbody Bag from Nordstrom Anniversary Sale 2021
In fact, I kept the entire outfit on the lighter side of the color spectrum, with this white tee and open cardigan in a leafy green. This green Caslon Open Front Cardigan is the only cardigan I purchased at the #NSale this year.

I don’t wear cardigans that often, but I like to have a few options for transition season, and this one is really soft and comfortable. I love the extra long ribbed cuffs and the the seamless pocket design, and it’s the perfect mid-thigh length.

This green color is selling out, but there are some other color options available. And if you love this color, I highly recommend calling your local Nordstrom store. I saw a bunch of these on the rack at my store on Saturday, and a lot of ladies in our facebook community have reported seeing items in their stores that are showing up as sold out online.

If you don’t have a Nordstrom store nearby, keep checking back online because there will definitely be restocks as people start making returns. When something you really want pops up in your size, I recommend paying the expedited shipping — that will help ensure your order doesn’t get canceled before it can be fulfilled.

This white tee is a workhorse in my wardrobe all year ’round. I pick up a fresh white one almost every year during the Nordstrom Anniversary Sale because you can’t beat the $12 price tag. I wear it alone with jeans and shorts, or as a base layer with sweaters and jackets. It has a flattering scoop neck, and it runs true to size; I wear the small.

the Best white t-shirt under $20

Also, don’t you love how this crossbody bag ties the whole look together? It is actually what inspired me to create this outfit.

I’m also wearing this Monica Vinader chain link bracelet from the #NSale, along with the Kendra Scott Liza Drop Earrings and part of the Madewell Story Set of 3 Layered Necklaces.

FYI, the Vince Camuto Welland Booties run small. I recommend sizing up half, if ordering.

And these jeans also run small. I have other pairs in this style in my usual 28, but I sized up to the 29 in this pair. Mother Denim is pricey, but the quality is top notch, and they are the most comfortable denim I own. They’re also made in the USA.

I hope this post helps demystify how to wear crop flare jeans with boots this fall. (See other ways I’ve styled crop jeans, for more style inspiration.)

I’m excited to start playing around with more relaxed denim fits and booties as we head into transition season.

Jo-Lynne Shane wearing Cropped Flares for Fall with Ankle Boots and Long Cardigan

Of course, there is a lot of summer left, so I won’t be styling a ton of fall outfits just yet. I definitely have plenty of summer content planned, but I had so many questions about this topic, I was excited to share what I discovered!

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photos: Alison Cornell

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31 thoughts on “How To Wear Crop Flare Jeans with Boots This Fall

  1. Looks great for fall but what happens once winter rolls around and it’s frigid snowy weather? That’s what’s perplexing to me. Any ideas so when we’re buying jeans we have an idea how we’ll be styling them come winter?

  2. Loved the jeans/boots combos. All my ankle boots are packed away in the attic for now, but I have several similar to yours. I also have several pairs of demi boot or cropped flared jeans that I love to wear now and will continue to wear with boots. It’s fun to try different combinations. Hope you get to travel to the Jersey shore for a quick trip. I only live 1-1/4 hour from Ocean City, my favorite shore town! We make day trips frequently! Praying that Paul continues to improve and heal.

  3. I enjoyed this post because I was debating whether or not to buy another pair of crop flares in a light color and have decided that because my booties are all dark (I did order one pair in a light brown) I am better to wait and get a pair in a darker shade. I’m enjoying the light denim, but I know that my style is better suited to darker denim in the winter as I wear a lot of dark green, rust, and black sweaters. My first Nordy box arrives today and I can’t wait to start trying things on!

  4. I don’t get used to flare jeans… I’m a lost cause, I’m afraid. I’m an irretrievably skinny jeans lover😂.And since I am 1,63 cms tall, I don’t think crop flares would work for me!All my jeans and pants, except for one which is a boot cut,are skinny or semi skinny as we say here… Love all your posts, especially those regarding sweaters and jeans and Fall/Winter outfits!!! I’m a Christmas girl, literally born in Christmas,so autumn and winter are my favourite seasons ☺️

    1. I get you. They definitely don’t appeal to everyone. 🙂 I am actually surprised that I ended up liking them so much, go figure!

      My older daughter was born on Christmas Eve. It’s definitely a special time of year to have a birthday.

      1. Yes, absolutely! it’s the most magical time of the year! Christmas girls are the best!I shared that with Caroline!🥰

  5. Love how you’ve styled this whole outfit! Question have you bought the Zella joggers before? And if so what size do you tend to wear in their line? I’m looking for a good black option for fall and see Nordstrom has some in the sale… I’ve seen a lot of things I like … wish there was a way to give credit to our American friends when us Canadians shop our sale🤷‍♀️Thanks

  6. Thanks for this informative post on wearing crop flare jeans with boots. It brings me one step closer to thinking that I can pull off this look.

  7. I sure do wish I had paid for expedited shipping when I placed my order last Friday at 5a for the chunky booties. I may see if I can reorder them and then cancel the first order, since I’d also like to get the white tee you are wearing and the Caslon cardigan, in a color other than the olive green. Since I live in the southern part of GA, wearing cropped jeans all year long is not a problem. I hope you are having a great day!

    1. Yeah, I have a hard time paying shipping, but in this case, it’s worth it b/c those orders take precedence over the thousands of other orders. I hope you managed to snag those pieces – they’re all good ones!

  8. I absolutely love cropped jeans and will keep my eye on this pair with the hope it comes back in stock. Regarding the Vagabond boots, did you order an 8/38 or a 9/39? I had thought an 8 was a 39, so I am unsure what size to order. Thank you!

  9. You always give such great fashion advice! Iam more excited than ever about the Nordstrom Anniversary Sale after you got me thinking about how to pair this style of jeans with all the great boots in the sale.

  10. How does this combination look when sitting? I imagine there would be several inches of skin showing? I sit most of the day….

  11. Tell Paul he is in my thoughts and prayers. I had emergency surgery to resection my colon after it ruptured. I had been diagnosed a few days before at the ER but had issues the day of my follow up with my physician. Everything went well but I was in the hospital for 10 days. I love your practical fashion advice and hearing about your family.

  12. Thank you for all your great posts. My question doesn’t have anything to do with crop flare jeans, but I’d appreciate your input. Do you think over 60 is too old to wear a dress with a smocked bodice? The dress looks super cute on, but I don’t want to look foolish.

  13. Great post all around! What are your thoughts on wearing the looser fit/flares/bootcut jeans with the chunky lug sole boots I am seeing so much of?

    1. I prefer the lug sole boots I styled in this post to the flatter, clunky ones. I need to play around more with those. I just FINALLY got the Franco Sarto pair I ordered last Monday – https://shopstyle.it/l/bwtAn. Evidently Franco Sarto shipped all their products from their own warehouses, and the rush shipping did not apply. ANYWAY! They’re cute as can be, so I need to play around with them and see how they work with the different styles of jeans.

      1. The Franco Sarto boots you mention above are really cute. Are they TTS? Just wondering if the tab in the back will get caught up on pants. I love this post and they way you try different boots with the jeans to show the difference. Thank you!

  14. I love the fall outfit boot parings! I like how the outfits and colors match as the booties blend in. Do you avoid socks with the booties? I never saw socks as necessary with booties given how they’re made.

    1. I don’t usually wear socks with booties unless it’s super cold. I wouldn’t ever wear them with the Vince Camuto Welland booties, but I would with the Chelsea boots I showed in the mirror selfies.

  15. The Welland boots are so beautiful, but my knees can’t hack the 3″ inch (or higher) heel, particularly going up and downstairs at work & church. I’m so bummed.

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