How to Style Bootcut Jeans This Fall

Greetings, friends! Yesterday I posted about what jeans are in style for 2021, and today we’re taking a deeper dive into how to style bootcut jeans this fall. Full-length straight and relaxed bootcut jeans are making a comeback, and I recently added this pair of high waist ripped bootcut jeans to my closet. I’m really liking this silhouette!

How to Style Bootcut Jeans This Fallwearing: sweater // jeans // boots // bag // sunnies // earrings // bracelet

These aren’t the bootcut jeans of the early 90s — low-rise and fitted through the hips and thighs. As much as I loved those at the time, this pair looks more modern and fresh to my eye with the high rise and relaxed fit. They have a 30 1/2″ inseam, so they require a bit of a heel or a seamstress, but I like the longer length with the relaxed fit because it’s slimming.

Also notice how they’re not as long as we were wearing them before. It used to be that bootcut jeans should end 1/2″ from the floor, with shoes on, and that’s still fine. But you definitely do NOT want to see them touching or dragging on the floor, and I actually think an inch or two off the floor looks a little more modern. I didn’t measure but I’d say these are somewhere in that range.

These are very subtle differences, I realize, but as they say, the devil’s in the details! Okay, maybe that’s not the right expression, but you get the point.

One of the best things about full-length bootcut jeans is that it opens up a whole world of shoe options. Almost any bootie works with these jeans because you don’t have to worry about the shaft height or width interfering with the hem of the jeans.

These are the Marc Fisher Gadri boots from the Nordstrom sale, but they’re back to full price for the time being. DSW has a very similar pair for under $100, and I’m sure there are other alternatives out there.

I prefer a bit of a heel with bootcut jeans, but it depends on your body type. If you have long legs, you can probably get away with a lower heel. You can also play around with the length of your top — a shorter top generally looks better when wearing a low heel because it lengthens the line of the leg.

In this case, I’m not wearing a particularly short top, but it’s not long and baggy either. This sweater vest (unfortunately low inventory) is about 24″ long. It’s also somewhat fitted, which is figure-flattering and helps off-set the extra volume in the jeans.

I also styled these jeans with a t-shirt and utility jacket. Because they have such a high waist, I front-tucked my t-shirt but bloused it out a bit over the waistband. The addition of the jacket on top helps keep the overall proportions in check.

These boots also have a 3″ heel, but with an additional 1″ platform, so the jeans are definitely a good 2 inches off the ground. I like how the hem of the front of the jeans barely touch the top of the boot.

How to Style Bootcut Jeans This Fall: with Lug Sole Chelsea Boots

And then I played around with these jeans in my bedroom a few weeks ago. Here’s how they look with a fashion sneaker. I don’t love the way the jeans buckle on top of the shoe in front, but they’re okay from the back — they aren’t dragging on the ground or anything. It’s definitely a sloppier look than with the boots, but it might work for casual wear.

And this is a bootie with a 2 1/2″ heel. They definitely work with these, so they will probably work with a 1″ or 1 1/2″ heel just fine. This 30 1/2″ inseam is pretty versatile!

It will be interesting to see how this trend plays out as we get into the fall season. I’m still seeing a lot of straight crops on the websites (see how to style crop flares for fall) but I think we may start to see the return of longer jeans when cold weather arrives.

What say you? Are you on board with this trend, or are you going to sit this one out?

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photos: Alison Cornell

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30 Responses

  1. Great post Jo-Lynne! I bought the NYDJ Marilyn and took it to a seamstress to shorten 1/2 inch. I look forward to wearing them. I think my dilemma is( I do like the straighter styles) I am a speech therapist in the schools so I am on my feet so I cannot wear heeled boots much even though I like that look. it’s typically lower heeled boot, shoe, or I can comfortably wear a comfort heeled sandal like Dansko, Ecco, ect. What do you suggest or how I can I pull off this great look without wearing high heel shoe/boots? Thanks!!

  2. Thanks for the posts from the past two days, I’m ready to shop for new jeans now. I love the utility jacket and am thinking of ordering. What size did you purchase? It looks like a loose, generous fit.

  3. I hope that you and Caroline have a great time today! I am all in for this trend in the style of our jeans. However, my challenge is that my bad ankles just don’t allow me to wear any shoe/boot that is over 1 1/2” high and there’s no seamstress in our neck of the woods. Surely I can find a pair of bootcut jeans that aren’t as long.

  4. Love this look. I’ve always liked a nice boot cut, flattering to most and looks classy with the right top. I need to find a mid-rise boot cut. These high rise cuts are not comfortable for me. Hoping I already own an appropriate boot or two or three in the closet arsenal. Thanks for the crystal clear tips. Enjoy your special day with Caroline. We’ve done this with 3 kids. Painful each time. Hugs to you.

  5. Yay! my favorite type of jeans! The website says those have a 13″ rise–wow that’s high. Particularly for short-waisted Gals, although I know you fit that body-type, and it appears you are okay. Thanks for the tips on length etc. That helps

  6. I love straight leg and boot cut jeans, so I am thrilled to see these returning! I ordered the NYDJ Marilyn and they should arrive today. I love the pair you are wearing in this post, but needed a shorter rise and longer inseam. I agree with the others that I would love to see these styled with a lower heel, especially since I have long legs.

  7. When running errands I find I’m more comfortable in a sneaker. Any idea how these jeans will pair with a sneaker for the gals on the go?

  8. I am on the hunt for a non distressed jean with a higher rise (around 10”) that have an inseam of 30 to 30 1/2”. So far I have ground the NYDJ in the Marilyn straight leg that has a short inseam (not petite) that works, but they are very hard to come by. Any help would be appreciated.

  9. No one else has mentioned this, but the link in my email this morning took me to yesterday’s post. I had to go to your website directly to find this post.

    You look great in these jeans. Sadly, I’m several inches shorter than you and can’t wear heels, so they won’t look nearly so nice on me. That “may” not stop me from trying them!

    1. If you wear a pointy toe flat bootie, you will get the same look Bonnie. Bootcut lengthens the leg so I think you’ll be pleased.

    2. Bonnie….I had the same issue. It linked me to yesterdays post and I just now went to find it. I emailed Jo-Lynne to let her know.

  10. I’m just not ready for the bootcut style. I am too short to wear them with a low heel and I don’t want to run around in a heel all the time. They still look dated to me right now. I live in a small conservative town, so still can get away with my skinny jeans, but when I go an hour to the city, I see more of the straight leg or crop flare for sure. I decided when the bootcut went out of style and the skinny jeans came in, to save 2 of my bootcut in the back of my closet to just see when they came back if they’d be the same or change. I just threw them out. They were very low cut, tight in the thigh and very long and too big. LOL Just trying them on again made me NOT want them to come back in. You however look really good in these and the Kut from the Kloth that Cyndi styled with the shacket were cute on her too. I think if you are taller, you can pull them off better.

  11. I’m seeing longer length everywhere..so much so that ankle jeans seem more like a summer thing.
    and…..COWBOY BOOTS. Yes, even with shorts. I do like them with a boot cut..I’m not sure I could pull off the look though.

    1. Oh my gosh the cowboy boots – yes! We have several brand new teachers at my school this year and they’ve been wearing cowboy boots with short dresses and skirts! They look so cute! (But they’re also 25 years old.😉) I’m wear flat shoes now everyday (sandals or sneakers) and can’t imagine teaching now in any shoe that isn’t super comfortable.

  12. Thank you for the post Jo-Lynne! I am close to San Francisco and I’ve been seeing highvwaist crop flares or what I think is the younger girls wearing the new mom jeans. The shoes are a close fitting lug sole boot, either Doc Martin style in look or a hidden zipper on a rounded toe boot. It looks really comfortable and modern. Have you got a grown up version in mind for us readers? The best example is the post of your daughter Becca with the white boots and plaid top and shorter jeans. Is there a mom version?

    1. That look is tough to pull off for ladies of a certain age. It can be cute if it fits your personal style, but it’s way too rugged for mine, plus I prefer jeans that are more fitted through hips and thighs or more streamlined like the bootcuts I styled in this post.

  13. Thanks for this post – so helpful! I have cigarette jeans (black and medium wash) which I wear with leather sneakers on repeat thanks to your encouragement. You helped me nudge onto the sneaker trend and found a cute pair of Roxies beige sneakers with a leopard detail that works with everything. Thank you for helping me stay current and nudge me out of my fashion ruts! Have a fab Mom/ daughter day getting mani-pedis and lunch. You have a lot on your plate right now with moving Caroline and your husband’s upcoming surgery. Thinking of you and praying for you. ” This too shall pass” as my Mom says.

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