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Boots with Jeans on women
images: Pinterest

What a mistake! I purchased one size too big and picked the wrong style of boot to fit over my skinny jeans or under crop flares!

Standing in line at the Post Office, feeling hot and agitated, while returning my bitter failed online purchase. There must be an easier way for me to know which styles of boots work with my jeans? A Personal Stylist would be nice, HOLD ONI am a personal stylist!

It was then I realized that I needed a plan to visualize ( I do love creative visualization) the different styles of jeans and boots that would work well together as I wanted to avoid being in line here again!

 This simple checklist will empower you to shop for new season boots with a clear, no-fail plan…

Checklist to follow on wearing boots with jeans

Below is where you can virtually try lots of different styles of boots with similar jean styles you may have in your closet.

boots in the sky

Sit back and enjoy sliding the ‘boots and jeans’ below to see which combinations you like the best. Imagine it as a carousel in your walk-in wardrobe showing you all the options to go with your jeans. Feel free to get a snack!

Slide & Click to Shop 

Loose & Baggy Jeans

Loose & baggy styles are so on-trend right now! They’re often paired with a sneaker but ankle boots can be an option to elevate this look.

Slide & click to look at this selection of boots and jeans that work with Loose & Baggy Jeans

Straight Crop & Kick Flare Jeans

I get asked this question a lot ” how do you wear crop jeans /flares in Winter without getting your ankles cold?”

So, the way to wear straight crop jeans in the Fall is to opt for an ankle boot that kisses the hem of the jean or tucks under neatly. Kick flares look best with an ankle boot tucked under the flare not showing any leg.

An ankle boot that sits close to the ankle is ideal so you don’t get any bulkiness in this area. The tall Chelsea ankle boots are perfect!

Slide & click to look at this selection of boots and jeans that work with Straight Crop & Kick Flare Jeans.

Skinny, Slim & Straight Jeans

If you’ve stopped wearing skinny jeans ( I have a pair on as I type) you may want to think again, as nothing looks nicer than a Tall Boot worn over jeans. Ankle boots pair well with straight-leg jeans with a turn-up.

Did you know, if the ankle boot is the same color as the jeans your wearing it makes you look taller? Try it and let me know in the comments below.

Slide & click to look at this selection of boots and jeans that work with Skinny, Slim & Straight Jeans


Boot Cut & Flare Jeans

Boot Cut & Flared jeans are similar when it comes to which boots to match them with.

The difference is:

  • Flares kick out from under the knee.
  • A Boot Cut kicks out from the calf area.

In the 1850s sailors wore boot-cut trousers that fitted over their boots with ease. Cowboys followed suit paring a cowboy boot to the boot cut jean. Fashion has changed the original cowboy boot and as you can see below the Western-style takes on many guises.

Slide & click to look at this selection of boots and jeans that work with Boot Cut & Flare Jeans


The Reveal – What worked for me!

I took my own advice (always a cocktail after shopping) and the boots (below) are the style that seems to work with my skinny jeans (over jeans), crop flares (under jeans – showing off the boot), and flares or bootcut (under jeans – showing the toe & heel).

Moda in Pelle has a great selection of boots with different heel heights for Fall.

Can’t choose between two styles? Buy both and send one back. At least this time you’ll line up at the post office proudly wearing your perfect choice of boots.


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Print out / screengrab this Boots  + Jean's quick guide:
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Now you know which boots to wear with your jeans check out which shoes to wear with your jeans.

Get more shoe & jeans inspiration – Free Printable

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I’d love to hear what you think about this post! Any questions please comment below & I’ll be happy to reply!


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