over the knee boots, fall trends, how to wear over the knee boots, how to style over the knee boots, how to wear flat over the knee boots, winnipeg fashion blogger

Grey Sweater Dress and Over The Knee Boots

In Fashion, Outfit of the day by wR23Fs2Sqi47 Comments

Happy Halloween! I hope you had a great weekend. As I sit here tonight writing this post, I find my mind is a bit scattered. My heart is with my brother and his family. This past week, he underwent surgery to have a cochlear implant put in his right ear. The procedure went well but while they were running some tests, they discovered he has another tumor (benign) growing behind his left eye. It will have to be removed and there is a risk he might lose his sight. Needless to say, our family is praying that this doesn’t happen. It breaks my heart to think he may not be able to see his boys grow up. But we have faith and we trust in the power of prayer. And even thou we might not see a way right now, we know God has a way💗

On a much lighter note, I’m on the hunt for the perfect pair of over the knee boots. One thing I really love about over the knee boots is it’s a style that you can wear both day and night. And they’re perfect for chilly fall days and nights. Anyhow, I bought these last year from an online clearance sale. At the time, I didn’t take in to account the fit. To be honest, I think I was blinded by the crazy cheap price point. Lol! In hindsight, I wish I had taken the time to look for a style that was more snug and less baggy. I find that these boots keep bunching at my knees which is super annoying. I should have pick a style with a back lace up closure so they wouldn’t slide down so much. Or maybe a stretchy style which works better for those of us with smaller calves.

Dress: Style Bar (similar)   Necklace: Hush   Boots: Shein (similar)   Bag: Rebecca Minkoff (similar)  Watch: c/o Jord  
Ring: Lia Sophia  

If you have a go to brand for over the knee boots, let me know because the hunt is still on 🙂

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Have a great week!

xo, Jackie

Linking up with: #HowIFall/ Classy Mondays/ Hello Monday/ Oh Hey Girl/ Style Me Wednesday/


  1. Jackie hon, first of all I’m very sorry to hear about your brother, I hope and wish him the best with regards to the outcome of the surgery. Life…as for your boots, I love this Puss n Boots look, but you know what, I never get why people buy shoes online- nooooOOOoooOO! I have a ritual when I buy shoes- I walk up and down, I do a lil’ dance, I do all that jazz to make sure the fit is right. Luckily coz of your slim frame the boots have a cool lil’ slouch appeal. Have a good week ahead. x

  2. I’m so sorry to read about you brother! I’ll be keeping you and your family in my prayers. Also, you look really lovely in this dress!

    By Lauren M

  3. I am so sorry to hear about your brother. I can only imagine that must be difficult and scary news to digest. Prayer is so powerful though! On a lighter note, I really love this sweater dress. So perfect with your boots. I think your pair looks great, but I totally know what you mean about the fit.

    Amy Ann
    Straight A Style

  4. Good morning! You look beautiful and you made the boots work even with an unpleasant fit:) The results were beautiful portraits. I encourage you and your family to let God be the ultimate picture straightener in your brothers life by continuing to have faith and believe in his promises. I will continue keeping him in prayer. Blessings & Love to you


  5. I am very sorry to hear the sad news about your brother. I hope everything will work out well and keep faith!

  6. I will keep your brother in my prayers, Jackie, and believe with you and your family that he will not loose his vision and most importantly, that the tumor will dissolve (I’ve seen this happen!). As for your outfit, I love it! I love the way OTK boots look paired with dresses, I always feel like there’s a bit of a ’60s mod vibe the duo create. Perhaps you can opt for a style that has a draw string in the back, so you can adjust it to your leg size? I hope you’re having the best day, beauty, and thanks so much for sharing!



  7. I am so sorry for your brother my dear Jackie! I wish for him to be strong and to have the quickest recovery!
    As for your look, I really like how effortlessly chic it is and the otk boots with sweater dress! Your bag is fantastic, what a great color!
    Wishing you and your family all the best and a great November! <3

  8. You are so right about styling OTK boots day or night. I love them for both day or night and you can pair so much with them. I am on the look out for boots just like these. I love the ones you have and the ones I have right now are heels and I just want a flat comfortable cute boot.
    This fall look is perfect, Jackie.


  9. Shoutout to the small calve movement!
    But no one can tell you were having bunching issues, your pictures are flawless as usual.

    And very sorry to hear about your brother. On one hand they found the tumor before it had a chance to cause any problems, but on the other hand you have this terrible risk to face as part of removing it.

    I’ll keep him in my thoughts girl but you guys stay positive <3 <3

  10. I love this jumper dress, it looks so great paired with the knee high boots! Have a lovely weekend 🙂


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