25 Days of Fall Fashion: Styling Bootcut Jeans for 2018

Hello, friends! Happy Saturday! It’s T-I-M-E for 25 Days of Fall Fashion!!! This is when I team up with my fashionable friend, Cyndi Spivey, and we each style a new fall outfit every day except Sundays for the month of September.

If you’re here visiting for the first time, welcome! I’m Jo-Lynne, a wife of 23 years and mom to three kids — one in middle school, one in high school, and one in college. We live in the suburbs of Philadelphia, and I’ve been sharing my life and style here on this blog for over 12 years. I love doing these style collabs because they force me to step out of my comfort zone and style looks I might not otherwise try.

Today is a great example. My regular readers know that I love my skinny jeans, but I realize they’re not the best silhouette for every body type. I’ve been getting requests to show other denim styles, so today I’m styling a new pair of bootcut jeans that I recently discovered along with a gorgeous wear-everywhere scoop neck sweater.

These jeans are from Express, and I love the fit. They’re incredibly flattering, and they also have a really nice looking wash that’s hard to find in jeans at this price point. You can see more of them in this try-on haul I posted last week. For size reference, I usually wear a 6 or 8 in pants, and I’m wearing an 8 regular.

I paired them with this gorgeous purple scoop neck sweater from Loft. I discovered this sweater when I was in the store last week, and I was drawn to the color first and foremost, but it’s also got a super soft tight knit weave and a flattering scoop neck.

V-neck and scoop neck tops help minimize a larger chest and wide shoulders, so they’re my favorites, but I sometimes make exceptions. Fortunately in this case I didn’t have to!

It also has raglan sleeves and a shirttail hem, which I left untucked. I usually wear a small at Loft, and this sweater is true to size.

I also picked up this necklace when I was in the store. Doesn’t it fill the neckline perfectly? It’s adjustable, which is really nice.

I’m of the opinion that bootcut jeans look best with a heel, and conveniently, these Express bootcut jeans are the perfect length for me when wearing a 3¾ — 4″ heel, which is often what I end up buying in pumps and booties.

The heel on these sandals is 4 1/4″ (although they don’t feel that high at all.) I wouldn’t want these jeans any further off the ground, but they work.

These sandals were an #NSale purchase, and they’re perfect for this transition season. With the slingback heel and open toe, they keep my feet cool in warm weather but they look like fall.

They’re incredibly comfortable for a 4″ heel, the inside is smooth and soft, and the chunky heel provides stability. I actually sized down a half size in these, and I recommend trying that if you have narrower feet.

While they’re dubbed “sandals” on the Nordstrom website, I’d call them open toe booties, but whatever you call them, they’re super cute and on trend with the ruched cuff and pinpoint perforations. Pairing bootcut jeans with a modern shoe like this helps keep the look current.

Finally, I carried my taupe crossbody (similar here.) I don’t always match my bag to my shoes, but in this case, I thought it made sense.

I love the combination of grey and purple, and it keeps the whole look more streamlined than if I’d introduced another color.

This outfit is really quite simple — a sweater, jeans and booties/sandals, but the jewelry dresses it up and the block heel sandals keep it current and on trend.

shirttail sweater // bootcut jeans // booties // handbag // necklace // earrings

photo credit: Alison Cornell

Don’t miss my Labor Day Weekend Sale Roundup, and be sure to visit Cyndi to see the fall outfit she’s styling today!

Lower Heeled Bootie Options:

More Bootcut Jeans I Like:

Don’t miss a post!

Subscribe to get email updates! In addition to my most recent blog posts, you’ll receive exclusive newsletter content like special sales, my newest favorite finds, and an occasional peek behind the scenes — all delivered right to your inbox. PLUS you’ll be automatically entered for a chance to win a $50 gift card each month, so don’t miss it!

This post contains affiliate links. When you shop through my links, it helps support my business (at no additional cost to you) so thank you!

Join The Conversation

37 Responses

  1. Fabulous outfit! I love the fall fashion series. I started reading this at the gym and it totally threw off my whole workout lol
    Fashion and fitness are two of my great loves (there’s also my awesome husband and kids and God, but fashion and fitness are high on the list too)

  2. Yay! My favorite series of the year. Love this outfit! The sweater is such a pretty color and looks great with the grey.

  3. Love this look, Jo-Lynne!  Question: what size are the jeans & sweater?   I’ve never worn express jeans and wasn’t sure if I should size down/up. Thanks  for taking the time to have the fall fashion series in the midst of everything else going on in your life.  I have enjoyed seeing all the updates to your new home .  Would love to see a rug update whenever you have time – i’ve been scouring the Wayfair website trying to figure out some rugs for my home as well .  Hope you and your family have a terrific Labor Day .  There’s nothing quite like having them all under one roof. 😊

  4. Thank you for styling bootcut jeans! I can’t wait to start wearing mine again. And I also wondered if they were ok to wear with open toe booties, and you showed that they are. Thank you! 

  5. Ha… I love how you and Cyndi styled the same sweater… it’s nice to see just how versatile the sweater is seeing it styled both ways, and two  beautiful colors. Sorry it’s raining again.. that hadn’t been our problem here this summer very hot dry and humid weather.., and very little rain. I hope we don’t pay for it in the winter… 
    have a great Labor Day weekend 😀

  6. My new favorite color for fall
    Never really thought of it as fall color!
    Enjoy your weekend raining in Chicago also!

  7. Way to knock it out of the park on the first day! I love everything about this outfit!! Even the boot cut jeans that I swore I would never do again!

  8. I got 2 pair of barely boot jeans on sale a few weeks ago from Talbots. I love how they are not too wide but not straight. Can’t wait to wear jeans, sweaters & booties. Still hot here but it’s Sept so cool coming. I hope.

  9. Beautifully classic! I just ordered two pairs of the Express jeans thanks to your blog. I remembered I had a pair several years ago that I wore until they fell apart. They fit my hourglass to a T. You look great!

  10. Beautifully classic! I just ordered two pairs of the Express boot cut jeans thanks to your blog. I remembered I had a pair several years ago that I wore until they fell apart. Skinny jeans just do not flatter me; but boot cuts do! They fit my hourglass to a T. You look great!

  11. Beautifully classic! I just ordered two pairs of the Express boot cut jeans thanks to your blog. I remembered I had a pair several years ago that I wore until they fell apart. Skinny jeans just do not flatter me, but boot cuts do! They fit my hourglass to a T. You look great!

  12. Jo-Lynne you look so cute in this outfit. This is one of those that could be dressy by amping up the jewelry and shoes or more casual. I like the bootcut on you. I am traveling for 2 months so gotta figure out how to get some orders in! Have a lovely weekend! ( would love to see more of your house as you go along). 

  13. Love the color combo of purple with grey – looks fantastic on you! The booties are a nice touch. On my wish list.
    Fall fashion series, pumpkin spice latte and College Game Day tv show – I’m one happy lady this morning! 😉

  14. The sweater is a beautiful color on you.  Fun to see you and Cyndi wear a different color and style it different.  I never would have thought of either color for Fall, but need to think outside the box.  I’m still not ready for bootcut jeans, but sure I will get use to them.  I learned to never say NEVER with cuts of jeans. You look great in them.  Great start to the Fall series. I’m so ready for Fall.  But, sounds like we are going to get hot again.  We live in an area like yours, but the opposite coastline and we’ve been drier than usual this summer, so hate to say but I’d love a rainy day. 🙂  

    1. I never say never either! At least not in matters of fashion. 🙂 Sometimes rainy days are nice, but we have had far too many of them this summer. Fortunately it cleared up yesterday and we had a really nice night last night in the pool with friends.

  15. I love this outfit and how you put things together. I’m looking forward to the rest of your 25 days of fall! I have also enjoyed the posts about your new home!!

  16. Great way to start off the Fall series! I love the color of the sweater and the bootcut jeans. I used to wear bootcut but seeing them trending again makes me think I need to buy a new pair! 

  17. I really like how you styled all of the elements into one great outfit. I’m looking forward to the gorgeous weather that September often provides. This summer has been so hot and humid most of the time….my least favourite weather. Enjoy the long weekend with everyone under one roof.

  18. Finally my iPad is cooperating so that I can comment.  I read the post this morning and have been looking for low heeled peep toe booties with arch support.  I have found one pair, so I just might have to give them a try.  You look nice in the bootcut jeans!  Way to go on giving them a try!  I hope that the rain will stop soon, especially in the flooded areas.  Hope you’ve had a good day!

  19. Do you know if it is possible to order at Nordstrom and request delayed shipping? We are leaving town for 3+ weeks and there will be no one here to pick up packages. Thanks!

  20. Yay bootcuts! Getting a little tired of the skinnies all the time (not you styling them – me wearing them ;0). I ordered these jeans and the Kut from the Kloth lighter wash ones. Love the sweater, too. Thanks for the bootcut outfit!

  21. Great outfit! Loving the top in that color and excited to see a raglan sleeve. I’m seeing dolman sleeves everywhere on sweaters but to me they seem a bit sloppy and emphasizing my upper arms with a seam is not what I need. Loft has such great range of sweaters this season.

  22. Love this new fall outfit and the color blend. Clicked on the sweater link but the color you’re wearing doesn’t even show as an option in any size so I’m hoping your post as least sold it out!

  23. Love this sweater! It seems to be more of an orchard color in your photo and more of a darker purple online – which would you say it’s like in person?

  24. I wear boot cuts all the time and had been doing it since they first came out regardless of trends. I think they give you a better silhouette than skinnies and I like to have more than one choice in jean cuts. You demonstrated that flares and boot cuts can look nice and they are a staple that never really went out of style and it is the choice of many to wear anyway.

Leave a Reply

Your email address will not be published. Required fields are marked *

Close this search box.