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How to Style the Best Pair of Shoes for Skinny Jeans

March 4, 2025 by TheChristianMamaMemoirs 3 Comments

If you are a millennial mom like me, you are more than likely still rocking the best pair of skinny jeans. As of March 1st it has come to my attention that skinny jeans are being brought back by Gen Z ( I didn’t know they went anywhere) and are considered Y2K fashion. What? I guess as millennial mom that still wear skinny jeans, we are probably part of this community. However, it is a bit nerve wrecking to me that my favorite skinny jeans are now considered Y2K fashion. To be honest, I am not even sure when these tight jeans went out of style. They have always been a great choice for me, and I cannot remember the last time I wore wide leg jeans or straight leg jeans or bootcut jeans or baggy jeans any other jean style. However, I do opt for the controversial “leggings as jeans” style on occasion. Anyways, let’s get to the point.

By the way, I will have shoppable links available for you in this post. Everything will be available on the infamous Amazon.

The Classic Choice: Skinny Jeans

Okay, so maybe you haven’t been rocking skinny jeans since 2008 or maybe you took a short break and are ready to dive back into the sleek silhouette that skinny jeans are known for.

So, my absolute favorite skinny jeans at this stage in life are actually Jeggings. That still counts right? They’re also Amazon brand and less than $20. After having my first cesarean section, I bought these jeans in every single color, and I still wear them while pregnant with my second son. They look just like jeans, but unlike denim styles they allow for more movements–which is essential when chasing around a toddler. Additionally, I just find the fabric to be more comfortable than denim and they still give me the support I need around my mom belly. Also, they are available in Plus Size. That being said this is of the most universal choices today when it comes to shopping for a skinny jean.

Dark Skinny Jean (Dark Wash)

Black Skinny Jeans

Khaki Brown Skinny Jeans

Light Wash Skinny Jeans

Medium Wash Skinny Jeans

White Skinny Jeans

Indigo Wash with White Pola Dots Skinny Jeans

Let’s Talk About Shoes for these Slim Jeans

Now, many women love to wear a kitten heel with these jeans & yes that is a great choice. However, the purpose of this blog is to empower moms, and typically the best shoes for moms that are out and about with their kids does not have a heel, unless it’s a chunky heeled boot.

Here are some of my favorites to pair with skinny jeans while maintaining little ones.

  • Ankle Boots
    • Ankles Boot are 100% my staple choice when wearing skinny jeans. I have three different pair that I love to wear on a regular basis, and I will link them below or similar versions.
      • Calvin Klein Women’s Dhara Ankle Boot (Brown)
      • Calvin Klein Women’s Dhara Ankle Boot (Black)
      • Michael Kors Rory Flat Bootie (Brown)
        • My personal Favorite
      • Michael Kors Women’s Carlisle Flat Bootie(Black)
      • Michael Kors Women’s Carlisle Flat Bootie (Dark Brown)
      • Michael Kors Hamilton Flat Bootie
  • Ankle Rain Boots
    • I wear ankle rain boots almost all winter long & yes I wear them with my skinny jeans. I will link similar options to what I have below, or the exacts pairs.
      • Hunter Women’s Original Chelsea Boots
      • Lands’ End Waterproof Rain Boots
      • Micheal Kors Mac Rain Boot
  • Knee-High Boots
    • I do love a good flat knee-high boot. There was a time in my life where that is the only thing I would wear out of the house.
      • SUEDI Slouchy Knee High Boots
      • Lucky Brand Women’s Calypso Boot (Dune)
      • Lucky Brand Women’s Calypso Boot (Black)
      • Lucky Brand Women’s Calypso Boot (Falcon)

Ankle boots are my absolute favorite shoes to wear with skinny jeans. I personally love the overall look and not having to worry about them untying on me. They are such a great option for anyone.

Some other styles of boots that you may consider could be combat boots, cowboy boots or western boots, chukka boots, or even a sock bootie. I personally do not own any of these pair of boots so I could not give you an honest recommendation. My suggestion is just finding one that you like, you cannot go wrong with skinny jeans and a pair of boots.

Some other options would be ballet flats.

  • Amazon Basics Knit Ballet Flat
    • These flat shoes come in many different neutral colors and some prints, and they are less than $15.
  • Lucky Brand Emmie Flat
    • These flats come in even more colors and prints than the Amazon version. They range from $30 to $55.

Another popular choice of flat are the Mary Jane Flats. The difference between a Mary jane flat and a ballet flat, is that the Mary jane flat option has a strap over the top of your foot. This could be a useful feature when chasing down kids.

  • Rothy’s The Square Mary Jane Slip-On Shoes
    • Rothy’s are a great choice as they are made from recycled materials, making them fashionable and eco-friendly.
  • Lucky Brand Millit Mary Jane
    • These would be super cute in the summer with skinny jeans or dresses.
  • Cushionaire Woven Mary Jane with Memory Foam
    • Another super cute option for summertime. These ones do have a pointy toe. Honestly, I live in Michigan so anything that is not a boot is a summer shoe. I am not walking through snow or mud without boots.

Some people also love tennis shoes with skinny jeans, I am not one of those people so I will not be recommending any to you. We strive for full transparency on this side of the internet.

However, a flat campus sneaker does make a good pair with skinny jeans.

  • Rothy’s The Lace Up Sneaker
    • Again, eco-friendly and a pair of sneakers! Do the world a favor. They come in blonde, black, or as the classic white sneakers.

And those are all the recommendations I have for you.

I swear this list feels like it goes on forever, but I wanted to make sure I gave you awesome readers all the best recommendations that I have in order to create helpful content.

Click Here for the New Mom Outfit Checklist!

Click Here for Tips on Finding the Best Walking Shoes for your Infant or Toddler!

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Filed Under: Mom Health & Style Tagged With: fashion, mom, pants, postpartum, shoes, sneakers

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The Christian Mama Memoirs Blogger Kaitlyn King About Me

Hi, I am Kaitlyn. I am a single stay-at-home Christian mom of two boys, one of which is still baking in the oven. I am the owner and operator of a Licensed Home Family Daycare in the state of Michigan where I teach children about Christianity, in addition to preschool skills. I am a Domestic Violence Survivor and Advocate with a passion for Homemade Food and Health. Follow along with me for Tales & Tips from a Christian Mama every single week!

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