With so many jean styles on trend right now, it can be confusing figuring out which bootie goes best with each pair. I recently watched a terrific in depth video on how to style ankle boots with various jean styles. Watch the video below:

Booties come in three basic shaft heights; low, medium and high. I recommend us BA50’s have at least one in each category for effortless dressing. Showing a bit of your ankle is always flattering and elongating, so low booties work well with most denim styles. Medium shaft booties, which often have a walkable low to mid heel height, work great with our skinny jeans. However, with more relaxed fit denim, the hem can get caught in the bootie. If the pant leg isn’t too wide, as in slim straight silhouettes, this problem can be solved by cuffing the jeans. High shaft booties, which are tight to the ankle, are very versatile. Chunky and combat boots are in this category, along with higher heel dressier booties. They not only look great with most denim styles, but also work well with skirts and dresses. Below you will find lots of choices for booties in all shaft heights to pair with your denim this winter.


Low Shaft

Available in 4 colors, these highly rated ankle boots from Sam Edelman have a low shaft and comfortable heel. At Bloomingdales.

Pryce Ankle Bootie $160

Go with leather for waterproof or printed calf hair for fun—both are new classics to style up any wardrobe with just-right height. From Vionic, a brand known for comfort and wearability. In 4 colors.

Cecily Ankle Boot $159.95

An alluring western-inspired bootie from Sofft crafted from ultra-soft Italian leather. In four colors with a walkable 2 inch heel.

Aisley Bootie $164.95

Mid Shaft


Sleek, uninterrupted lines upgrade the look of a water-resistant bootie from Aquatalia made in Italy for comfort and style, whatever the weather. On sale in navy suede and also in black in limited sizing.

Ulyssa Water Resistant Bootie $299.90


A low heel brings walkable elevation to this leather bootie from Aqualtalia that goes with everything. Also in black.

Carisa Bootie $450


This lace up bootie from Sam Edelman is versatile and on trend. Also in white.

Garret Bootie $160


A ribbed topline creates easy-on styling and comfortable wear in this treaded bootie from Blondo. I own these boots and they are oh-so comfortable.

Hallie Bootie $150

This versatile black bootie by Sam Edelman has a square toe shape and a 5 inch shaft.

Thelma Boot $160

High Shaft


Everlane’s popular Glove Boot just got a raise. Introducing the High-Ankle Glove Boot—it’s made of the same textured ReKnit fabric as the original—with a higher shaft. Easy to pull on and designed to fit your foot like a glove. Plus, it’s made from renewed plastic bottles. In 4 colors with a walkable 1.75 inch heel. In my cart now.

High-Ankle Glove Boot $130

With a 3 inch heel and a 6 inch shaft, this boot by Dolce Vita will dress up any look and match most denim styles.

Indiga Boot $130

With easy pull on styling and a comfy platform, these boots from Phillip Lim are hip and cool.

Kate Platform Combat Boots $595


From Aqua at Bloomingdales, this bootie has a 3 inch block heel with a 6 inch shaft. Also in black and olive in limited sizes.

Juno Square Toe Bootie $148


These combat boots from Stuart Weitzman are chic and super comfortable. 6.75″ shaft. On sale right now at Bloomingdales. Also in black.

Sondra Shine Combat Boots $486.50


Choosing the Right Ankle Boot for Different Jean Styles was last modified: by

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