There is no more ubiquitous fall fashion trend than jeans and a pair of boots. While the specific trends and styles may change from year to year, the pairing of the two is an enduring combination for women of all fashion genres. However, the details on how to actually execute the jeans and boots combo can leave many women scratching their heads and wishing for a fashion fairy godmother. Your wish is granted today, because I am here to shed light on this mysterious subject and provide you with foolproof guidelines on how to wear your jeans with many different types of boots!

Jeans with Short Booties

I have amassed a large collection of short booties this season in a wide array of colors, heel heights and styles. From sock boots to ankle boots, I just can’t get enough of this versatile shoe choice. They are the perfect compliment to the 90s jeans styles that have made a major comeback and they also pair perfectly with my beloved skinnies. But, I know that it can be challenging for many women to decide how to wear a short bootie with jeans. Let’s take a closer look at how to style this fall fashion trend!

Skinny jeans bunched above a pair of ankle boots gives you the dreaded cankle!

Top Tips for Jeans with Short Booties

  • Skinny jeans should be cuffed right above the top of the bootie
  • Jeans with a cropped, cut-off hem that ends above the top of a bootie are a great choice
  • Wider leg girlfriend or boyfriend jeans look great layered over a sock boot that hugs the leg
  • Skinny jeans should not be tucked into the booties or bunching up around the top of the bootie
  • Contrary to what the name might suggest, bootcut jeans are not meant to be worn with short boots!
Green Cardigan Tan Booties

Skinny jeans cuffed right at the top of the bootie. This particular pair has a higher flap in the front that lays nicely over the top of the cuff.

Skinny jeans cuffed right at the top of an ankle boot creates a smooth, even line.

Sock boots hug the bottom of the leg and fit perfectly under the wider leg of a pair of girlfriend jeans.

Green Sweater Black Booties


Jeans with Tall or Over The Knee Boots

Over the knee boots and riding boots that end below the knee are extremely practical and trendy footwear choices for fall and winter. However, this is an area where I see so many women make big mistakes. Your regular boot cut jeans were not meant to tuck into a riding boot or over the knee boot and will end up looking sloppy and unflattering if worn in this way. A quality pair of fitted skinny jeans are an important investment to make when buying a pair of tall boots.

Baggy jeans that bunch around the knees or above your boots are a no-no!

Top Tips for Jeans with Tall Boots

  • Wear skinny jeans that are fitted throughout the leg with tall boots
  • Wear black jeans with black over the knee boots for a leg lengthening effect
  • Jeans should not be baggy or bunched up above the boots for this look to work

Light wash skinny jeans that are fitted throughout the leg create a smooth silhouette when tucked into over the knee boots.

Dark wash skinny jeans with over the knee boots.


If you want more info on boot trends, be sure to check out my post on sock boots!


All the ❤︎,