14 Best Tips on How to Wear Chukka Boots for Women

best chukka boots outfits for women

If you like playing around with different outfit ideas, there is a high chance that you are a fan of boots. Boots simply add a lot of character to your overall look. And with different outfits, you would like to pair with boots of different styles and different length. Many of you may be familiar with ankle boots and knee high boots. In this blog post, I am going to talk about something different: the chukka boots. For those of you who are new to this, chukka boots refer to lace-up boots that are usually shorter than ankle boots. Now, let’s check out some of my favorite chukka boots outfit ideas.

Chukka Boots with Oversized Grey Tee and Leggings

chukka boots grey tee leggings

Since chukka boots are kind of like high top shoes, you can wear them to replace the high top converse for your casual street look. For example, you can simply wear an oversized grey tee and leggings with chukka boots for a slighter tougher look than you would normally look wearing high top converse.

Wear with Long Sleeve Tee and White Down Vest

white down vest chukka boots womens

For a casual winter look, you can wear a long sleeve tee, a white down vest, and skinny jeans with the chukka boots. This is a nice outfit idea especially in one of those slightly warmer days in winter because it doesn’t make you look clunky at all. Instead it makes you look slim and smart.

Wear with Black Trench Coat & Skinny Jeans

black trench coat jeans chukka boots

This is an adorable outfit that is perfect for the fall and the winter. Pair a white tee and slim fit jeans with an oversized black trench coat and chukka boots. This is a good demonstration of how a slightly oversized coat can make you look slimmer. You have to be very careful though because all the pieces have to be in balance or you will look clunky instead.

Wear with Grey Slip Dress with Sheer Overlay

grey slip dress shear overlay chukka boots

For a beautiful spring look, you can wear a grey slip dress with sheer overlay and pair it with color-matching chukka boots. This is such a minimal and chic outfit that is actually quite easy to pull off.

Wear with Cropped Tee & Black Leather Jacket

cropped tee black leather jacket chukka boots

For a stylish and creative look, wear a green cropped t shirt with cuffed jeans and a black leather jacket. Pair your chukka boots with ankle boots for a more complex look with more layers.

Wear with Leather Jacket & Grey and White Striped Scarf

grey white striped scarf chukka boots leather jacket

This is another outfit idea that involves the black leather jacket but this one looks very different from the previous one. It has a darker tone with more elegance. Simply wear a white t shirt with a black leather jacket and black skinny jeans. Match the grey chukka boots with a grey and white striped scarf to complete the outfit.

Dark Grey Short Sleeve Knit Sweater & Black Mini Skirt

mini skirt grey short sleeve knit sweater chukka boots

Most of the time, chukka boots are paired with socks that either hides within the boots or extends about an inch beyond the boots. With this outfit, I am going to show you that they can be wore with black stockings too. For a smart casual work outfit, simply wear a grey short sleeve with black mini skirt. Pair with black stockings and black chukka boots.

Wear with Polka Dot Shirt and High Waisted Skirt

polka dot shirt high waisted shirt chukka boots

This outfit is just fun to wear. I really like it mainly because it involves one of the coolest item in the polka dot shirt. The shirt is not easy to put together with other pieces but this outfit shows you how to do it just right. For a young and adorable look, wear a black polka dots shirt with a grey high waisted skirt. Add a layer by wearing a cardigan. And finally the chukka boots and ankle socks match the outfit perfectly. If you like this outfit idea, you may be interested to check out our related blog post on polka dot dress outfit ideas.

Wear with Black Tie Waist Shift Dress

black tie waist shift dress chukka boots

Here is a low key beautiful outfit that you can wear to work. Wear a black tie-waist shirt dress with black chukka boots. You may want to wear a grey zip coat on top and carry a color-matching bag to look more balanced.

Sweater with Colorful Pattern

colorful pattern sweater jeans chukka boots

For a causal and stylish spring or fall look, you can still wear a sweater with colorful pattern and cuffed skinny jeans. Wear chukka boots and a watch to complete this slightly tough look.

Wear with Cargo Pants & Black Blazer

cargo pants white lace top chukka boots

As expected, chukka boots look wonderful when put together with jeans. If you want to try something different, try to pair the boots with cargo pants. As a smart casual work outfit, you can wear a white lace top and cargo pants with a black leather jacket. The chukka boots match perfect with cargo pants and the rest of the outfit.

Wear with Grey Wind Jacket & Skinny Jeans

grey wind jacket skinny jeans chukka boots

For a really casual look that still looks decent, you can simply wear a grey wind jacket and skinny jeans with the chukka boots. I can see this outfit as a good one for things like grocery shopping.

Oversized Printed Tee & Leggings

oversized t shirt leggings chukka boots

For a young and energetic casual look, just wear an oversized printed tee and leggings with the chukka boots.

Polka Dot Black Shirt & Black Knit Sweater


As a business casual work outfit, this demonstrates some nice layering technique that makes you look smart and professional. Simply wear a black polka dot shirt with a slim fit black knit sweater layering over it. Wear cropped skinny jeans and pair with the chukka boots to complete this smart and chic look.

I hope you like the list of my favorite chukka boots outfit ideas. I am sure you will look good with some of those outfits and you will probably like chukka boots as much as you like other kinds of boots. Before you leave, please check out our blog posts on all sorts of outfit ideas.