Naturalizer Jessie Women’s 100% Leather Knee High Boots

Last updated: September 11, 2023

Naturalizer Jessie Women’s 100% Leather Knee High Boots

Our Review Process

Don't Waste Your Money is focused on helping you make the best purchasing decision. Our team of experts spends hundreds of hours analyzing, testing, and researching products so you don't have to. Learn more.

Don't Waste Your Money Seal of Approval
Look for the DWYM seal for products that are the best in the category.
Show Contents

We looked at the top Women's Boots and dug through the reviews from some of the most popular review sites. Through this analysis, we've determined the best Women's Boot you should buy.

Overall Take

In our analysis of 21 expert reviews, the Naturalizer Jessie Women's 100% Leather Knee High Boots placed 21st when we looked at the top 21 products in the category. For the full ranking, see below.

From The Manufacturer

Riding boot silhouette with elasticized panel and buckle details provide style, while Naturalizer N5 comfort provides the extra padding that you require.

Expert Reviews

User Summarized Score

2,024 user reviews

What experts liked

These black buckle boots knee high style from Naturalizer are 100% leather with cushioning and a flexible sole to handle walking. And the neat looking buckles add some panache.
- Travel Fashion Girl
With a short heel, they’ll give you the look of height but you won’t be tipping around.
- Hello, Taee
It has an extra cushioned insole that is highly breathable; these boots ensure that your feet do not die inside them, and you can enjoy your flattering look with these beautiful pair of boots while your feet also live their precious life inside them.
- Guard My Shoes

What experts didn't like

A bit tight around the ankle
- Guard My Shoes


Booties can stop right at the ankle, below it or above it. Other boots hit at the mid-calf, below the knee or over the knee. Choosing the right pair of women’s boots starts with a purpose. Are they to match a certain outfit, for long periods of walking or just to look great?

If comfort is a priority, look for boots with memory foam footbeds or other kinds of arch support. Those that do not offer either may have room to accommodate separately-purchased arch support.

Be picky about heel height if you worry about comfort. Wedges can be great for high arches, while lower styles work well with flatter feet. Usually, the lower the heel, the more casual the look. If you choose 100% leather boots, they will last longer than man-made materials, but they also typically cost more.

Buying Advice

  • Be good to your boots and they will be good to you: Waterproofing leather boots can make them last longer, and if you avoid wearing your boots in wet or snowy weather, they will also stay in better shape.
  • Take fashion risks! Sure, ankle boots look great with jeans, but why not try wearing them with skirts or shorts? Look online for inspiration.
  • Look for features like side zippers and pulls on the backs to make the boots easier to get in and out of. If you have wider calves, you can find styles that have sizes to accommodate that.