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5 Ways To Wear Ankle Boots

5 Ways To Wear Ankle Boots 2This fall, the ankle boot is a fun fashion trend to wear. There are so many cute styles to choose from and they can make any outfit pop.

For some reason, I hear women say they struggle with how to wear them. I don’t think there is a wrong way but it often depends on the style of the boot.

So let’s look at 5 ways To Wear Ankle Boots.

5 Ways To Wear Ankle Boots 11. You can tuck your boot into your jeans. Especially if your boot has a high shaft, then it’s perfectly fine to tuck them in. This boot is the perfect example of tucking your jeans in your boot.

tuck them in your boot2. You can also wear the ankle boot with a skirt or dress. If you want to create a long lean look (which I do!), wear black leggings or tights with black ankle boots.

wear them with a skirtYou can also pair boots with a skirt or dress, without tights. I think keeping the boot close to the color of your leg looks better. It will help to create that long lean look.


3. You can do one large cuff. A large cuff can shorten the line of your leg so if you’re petite, this might not work for you. Make sure the cuff is no larger than 3 inches.

one large cuff
4. A neat rolled cuff is a great way to wear your jeans with an ankle boot. When wearing it this way, you do want some of your leg to show between the boot and your jeans. From everything I’ve read about an inch of leg showing is the perfect look.

neat rolled cuff
5. The messy cuff is such a cute look but not everyone can pull it off. Kilee from One Little Mama makes it look cute and effortless!

messy cuff
For women over 40, this is a great way to look stylish and trendy for fall! So have fun and go for it!

5 Ways To Wear Ankle BootsWhat do you think about ankle boots? Have you tried them this fall?

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Beauty For the Heart~~One of the things we do as women is compare ourselves to other women. Many times we can look at someone else’s life and think their life is perfect.

It’s easy when reading blogs to think the people behind the blogs have perfect lives (I feel that way too!). Someone left a comment on my sister’s blog a few months ago after she wrote an honest post about what she was struggling with.

The lady said (I’m paraphrasing), “I’m glad you shared your struggles, sometimes it looks like you and your sister (me) have perfect lives.”

I almost gasped out loud! Believe me when I tell you that we DO NOT have perfect lives.

I have hurts, and disappointments. My husband and I could write a book on all the hurts we’ve had in ministry and in our personal lives. Life is not perfect for any of us!!

Here is what I do know….I have a perfect God who loves me and understands all my hurts.

You keep track of all my sorrows. You have collected all my tears in your bottle. Psalm 56:8 (NLT)

Have a blessed day!

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  1. I just bought my first pair of ankle boots. It’s waaaay out of my comfort zone but I love how they look on others, so I wanted to try! Thanks for your tips! I especially love the cuffed looked but I’m 5’2 & I’m afraid my cuffs will be too bulky!! But I’m going to try anyway.
    Thanks again!

    1. Love, Love the ankle boot tips!! Thank you for sharing! Enjoy your blog and look forward to reading it each night when I get home from work. Always love reading your scripture messages and taking them with me daily.

  2. Love your message today Cyndi. ?
    You look great in all the bootie photos. Since I have short legs I prefer booties over taller boots but you are right about the cuffing. I roll my cuffs up just a tad so my legs won’t look any shorter.

  3. If you keep your faith in God everything else falls into place. I have to keep an orderly way of life and I know God is there at all times.

  4. I really enjoy your fashion tips especially for women over 40 as I am the same age as you 🙂

    As always, your scripture references are so inspiring.

  5. Thank you Cyndi for this post…wish I could talk a walk with you…you put so much in perspective…a very poignant message.

  6. Hi, Cyndi!

    I noticed in todays entry that you spoke about your sister’s blog. Could you give me the link to that? I really enjoy seeing your ideas with outfits and love the beauty for the heart! Thank you for posting!

    God bless!

  7. Love your truthful post. The only perfect life on earth was Jesus. And, then he suffered so much for us so that we may have the perfect life ever after. God’s grace. Gerri

  8. I love your message today. You never really know what’s going on in someone else’s life. Sometimes people think that someone with a smile on their face and a happy demeanor has a perfect life. Nobody has a perfect life. These people have learned to smile through the tough times knowing that it will get better. I feel that if we can be faithful and trusting during the tough stuff that we all go through and happy with the simple pleasures in our lives then we’ll always be content. Here’s a favorite quote: “The smile on my face doesn’t mean my life is perfect. It means I appreciate what I have and what God has blessed me with”. Don’t you love that?

  9. Great tips Cyndi. Being short, I do try to make my legs look longer with the tips you provided. Your “heart” tip is so true. Women can be so hard on themselves when we compare ourselves to others. I always love it when you and your sister share with us…even though you don’t have to. It’s very sweet and helps keep it real. You both are doing a great job !! Have a blessed day 😉

  10. I think I’m inspired to shop for ankle boots! What kind of socks do you wear with them? Something thin and invisible? or no socks?

  11. Cyndi, I just bought a pair of Frye ankle boots in a red color. Now I am not sure how to wear them since they are not black (tights) or tan (skin color). Also, I wear ankle jeans but not skinny jeans. Can I still tuck them in? How d I keep them from coming out of the boot? Thanks!

  12. I bought fringe ankle boots from Glamour Farms. Haven’t worn them out and about yet. I plan to wear them with a dress next weekend to our nephew’s rehearsal dinner. I’m 5′ 1, but I decided a long time ago if I like something and feel comfortable and confident I wear it! I’m 55, and excited about the 70’s influence in fashion this Fall!

  13. Thank you for your message today! I’m a work in progress, and won’t ever have perfection on earth…but so blessed 🙂
    Thanks for the ankle boot post…I struggle with how to wear them. I’ve been looking for a black pair of ankle boots. I have 3 pair of shooties & 3 knee boots…time to branch out 🙂
    Have a blessed day!

  14. Thanks for the tips on wearing ankle boots. Is it okay to wear your pant leg over your boot also? I like the look with my skinny jeans on my 5’2” frame. I think I read somewhere there is no wrong way to wear ankle boots. Would you agree? Anyway, I DO love them.

  15. Hi Cyndi, thank you for today’s words, they really helped me put my day in perspective. I enjoy your blog and reading the responses of other readers.
    Love the tips for wearing booties! I have one pair and am trying to decide what color to buy for a second pair!

  16. I love them, just bought a pair from Marshall’s in gray suede and I can’t wait to wear them!


  17. Love ankle boots and have a few pair of them that I try to create different looks! It’s fun! I love fall and the fashion associated with it- I live in Southern CA so I don’t get to wear some of the items I’d like all the time due to our weather.
    Thank you for your inspiring blog and posts. Always look forward to opening my inbox and reading what you’ve written.

  18. Thinking other ladies are perfect is this strange illusion that appears only to ladies. Men do not seem to compare, and determine they fall short, so easily.
    Currently I have 5 teenage children, work full time, and my parents are facing health issues , the best in my home I can do to lookl like I have it all together is: make sure the clothes are clean!! Lol..heck my husband did last weeks laundry!
    Another teacher said a ‘you seem perfect’ comment to me…I said honestly, ” I only washed my hair twice last week, we had grilled cheese sandwiches 3 nights straight, and I bought pumpkin spice candles because that is easier than washing the dog!
    But to end this long post, daily life is about showing Christ’s redeeming love at every blessed opportunity we are given, the rest is just the silly details:-)
    Cyndi rocks the short boot!!

  19. Im having trouble with my ankle boot look, as you said above I am only 5’3 so the rolled cuff makes me look even shorter, I’ve tried putting my jeans over the boot and tucking the jean in and it’s better but seems like you really can’t showcase the cute boot this way. I may try with skirt and tights all one color. I’ll keep experimenting but think I like my high boots with skinny jeans or leggings to be a bit more flattering for my height, I just got so excited about the ankle boot looks posted for fall.