How to Style Ankle Boots With Bootcut Jeans

Welcome back to my 26 Days of Fall Fashion! I’m so excited to be collaborating today with not only Jo-Lynne but also two more “over 40” fashion bloggers.

Cathy is a Dallas based fashion blogger and shares her fashion at The Middle Page, Deborah is the writer and fashion blogger at Fabulous after 40.

I met both of these ladies through the RewardStyle Conference and they are as sweet as they can be! We have stayed in touch and I love both their blogs and their style.

If you are visiting from one of their blogs, welcome to Grace & Beauty!  I’m Cyndi and I style fashion for women over 40 with reminders that true beauty begins on the inside.

So without further ado, we are sharing 4 Ways to Style Ankle Boots for Fall.

Deborah // Jo-Lynne // Cathy // Cyndi

Typically I style ankle boots with skinny jeans but today I’m styling ankle boots with bootcut jeans. I have branched out and started wearing bootcut and flare jeans and I love styling them with my ankle boots.

Bootcut jeans are named that because they flare out a tiny bit at the bottom to make room for a pair of boots to be worn underneath. That makes sense!

I think you can wear any style boot with bootcut jeans but I am partial to pointy toe ankle boots and these ‘Lettie’ ankle boots from Nordstrom work great with my baby bootcut jeans from Gap. (Gap is having a 40% off sale with code Fall4it but these jeans aren’t included.)

If you like bootcut jeans, you really need to give these baby bootcut jeans a try. I love them!

I’m also a huge fan of bell sleeves so when I saw this blouse from Loft, I knew I was wanted to style it. It’s a trendy blouse and would look great with dress pants too.

My crossbody handbag was in my recent Stitchfix box. It’s an Octavia Brooklyn Crossbody Bag.

bell-sleeve-top-16Ankle boots are a “must have” for me whether it’s peep toe booties, pointy toe booties or a round toe ankle boot. I love them all!


What I’m Wearing

Bell Sleeve Blouse (I’m wearing a small but I kept the tag on and I’m going to exchange it for an x-small)//Cami (I’m wearing a medium)//Baby Boot Cut Jeans (I’m wearing a size 28)//Pointy Toe Bootie//Necklace//Earrings//Handbag

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Make sure you visit Jo-Lynne, Cathy and Deborah and see how they are styling ankle boots!

I’m so honored that you have taken time out of your day to stop by my blog. If you don’t want to miss a post, you can sign up to receive my daily emails and you’ll never miss a thing. I’m also on FacebookPinterest and my favorite one, Instagram.

Beauty For the Heart~~The Lord doesn’t see things the way you see them. People judge by outward appearance, but the Lord looks at the heart. 1 Samuel 16:7b

Whatever you are pursuing externally will fade away. Your hair will gray, your waist will grow, and your skin will wrinkle.

But the inner beauty, the beauty that’s found in a relationship with Christ will not fade. This kind of beauty will grow as we pursue a relationship with Him.

What is your heart focused on today? The external or the internal?

Have a blessed day!

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  1. The whole outfit is perfect! I’m going to have to look into the boots, jeans and the bell sleeve top! Have a lovely day Cyndi!

  2. I just ordered those jeans as I had Gap Rewards and I decided using it on jeans that never go on sale is the best use! I am on the fence with the top, as I am not sure how in the way the sleeves would be during work (work at a computer all day)? But the outfit looks awesome on you!

  3. Good Morning Cyndi! I really like the bell sleeve top and the jeans. Question: When the top is a bit see through, requiring a cami, do you wear a strapless bra so that only one set of straps is evident? Thank you!

    Have a blessed day!

  4. I just purchased boot cut jeans at a Loft outlet. I am very petite & the 0P fit perfectly, even the length. Great dark color & they were on sale 50% off.

  5. Hi Cyndi

    You always look beautiful but I especially like this outfit!! Thanks for telling us about the 1969 Gap Baby Boot jeans – I’m loving them!!!

  6. You all are my favorite over 40 bloggers!!!

    You look adorable in the top but probably because I’m from the 70’s, it’s too “hippie for me.”

    I don’t think to use booties with long pants..but why not? Very fun post today!

  7. So the bell sleeves? I love the look but I’m afraid the big sleeves would drive me a little crazy, how are they to wear for any length of time? I’ve gotta check out those GAP jeans, they look great on you.

  8. Although I am a size 6-8 in most things, I don’t wear skinny jeans as much as boot-cut because I have heavy thighs and think the skinny jeans only accentuate them. I liked a straight-cut jean you styled in an earlier post, thinking it was GAP, and wondered if they might be a good compromise for me????

  9. Hi Cyndi, You look like an angel is those cool 70’s- inspired bell sleeves. Love the flared jeans and those elegant gray suede booties, So classy! Can’t wait to explore more trends with you! Cheers, Deborah

  10. Cyndi, I love those jeans. I’d love to know what length those jeans are. I can’t go try on so need to online order. Short, Regular, Long??

  11. I love bootcut jeans and the bell sleeve top, I have been watching this top for awhile, now that I have seen it on you, think I’m gonna have to but it! Have a great afternoon!😊

  12. What an adorable outfit! I love every piece of it. Based on your comments about the Gap baby bells, I bought a pair last weekend. Love wearing them. As an FYI regarding the sizing, I started off trying 29 and 30. this wonderful employee Patty helped me with the sizing. She had me try on the 28 then 27. Who knew! She said because of the stretch, I needed to go down in size. I was a little doubtful because they were sooooo fitted when I first put them on, but they then morphed into extremely comfortable jeans. They fit perfect and no bagging. Thank You Cyndi! I am off to buy the top and pocket book

  13. Cyndi,

    I love reading your blog! Thank you for sharing your life, fashion tips, and your love for our Lord! I’ve bought several pieces you have styled and I adore your fashion sense!!


  14. Love Gap’s bootcut jeans. I bought several pair at the Gap outlet, and I wear them all the time. So hard to find jeans that fit, feel good, and look great. Their bootcut and straight leg are great! Still need to think about ankle boots. I need to step (pun intended) out of my comfort zone and try on a pair.

  15. This is a cute date night outfit on you…I say on you because these items look waaayyy better on you than the models online. I would never even think of buying these from looking at the store sites. Keep up the great work and have a blessed day! God is good! 🙏🏻

  16. I bought that blouse on Saturday at 40% off. I got an extra small and plan on wearing it tomorrow! We get to wear jeans at my school on Fridays. Hopefully the sleeves won’t get in the way of my teaching;) Not ready for boots yet…you however look fabulous.

  17. Hi Cindy! As soon as I saw your top I knew I had to have it. Went to Loft on my lunch break yesterday and bought it and LOVE LOVE it! Thank you!!

  18. I love the ankle boots with the bootcut jeans. That is my favorite way to wear them. I’m so glad you’ve been styling some bootcut jeans lately. I think the bootcut jeans make me look more balanced, since my tummy is my problem area. I love the outfit you’re wearing here. The blouse is gorgeous.

  19. I love this outfit! I found your blog via the Fabulous After 40 blog. I bought the shirt and it came in today. I normally wear a small, but purchased the XS and am glad I did. It fits perfectly and is so pretty. I already have boot cut jeans, similar booties and a cute purse that will go great with it. Thanks!

  20. Hi Cyndi, I have straight length jeans that go over my wedge booties and I don’t like the way they look. I’m 5’1″ and my weight is 170. What is the best way I can wear my Jean’s with my wedge ankle booties. Thank you so much and hope to hear from you soon. Merry Christmas.

    1. Monica I would probably need to see a picture. I think that is the only way to wear straight leg jeans. Maybe try a pair of boot cut jeans. They are universally flattering on all shape and sizes.