How to wear chukka boots

How to wear chukka boots

If you like to play around with different outfit ideas, there is a high chance that you are a fan of boots. Boots just add a lot of character to your overall look. And with different outfits, you want to match with boots of different styles and lengths. Many of you may be familiar with ankle boots and knee-high boots. In this blog post, I’m going to talk about something else: the chukka boots. For those of you who are new to the field, chukka boots refer to lace-up boots that are usually shorter than ankle boots. Now let’s look at some of my favorite chukka boot outfit ideas.

Chukka boots with an oversized gray tee and leggings

Chukka Boots Gray T-Shirt Leggings

Since chukka boots look 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 gray t-shirt and leggings with chukka boots for a slightly tougher look than you would normally do with a high-top converse.

Wear it with a long-sleeved t-shirt and a white down vest

white down vest chukka boots women

For a casual winter look, pair your chukka boots with a long-sleeved t-shirt, white down vest and skinny jeans. This is a lovely outfit idea especially on one of those slightly warmer winter days as it doesn’t make you look chunky at all. Instead, you look slim and smart.

Wear it with a black trench coat and skinny jeans

black trench coat jeans chukka boots

This is an adorable outfit that is perfect for fall and winter. Pair a white t-shirt 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 as all the pieces have to be balanced or you’ll end up looking chunky instead.

Wear it with a gray slip dress with a sheer overlay

Gray Slip Dress Shear Overlay Chukka Boots

For a beautiful spring look, you can wear a gray slip dress with a sheer overlay and pair it with tonal chukka boots. This is such a minimalist and chic outfit that it’s actually quite easy to take off.

Wear yours with a cropped t-shirt and a black leather jacket

short t-shirt black leather jacket chukka boots

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

Wear it with a leather jacket and a gray and white striped scarf

gray 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. Wear gray desert boots with a gray and white striped scarf to complete the look.

Charcoal short sleeve knit sweater and black mini skirt

Mini skirt gray short sleeve knit sweater chukka boots

Most often, chukka boots are paired with socks that either hide inside the boots or protrude about an inch beyond the boots. With this outfit I show you that they can also be worn with black stockings. Just wear a gray short sleeve with a black mini skirt for a smart casual outfit. Pair it with black stockings and black chukka boots.

Wear it with a polka dot shirt and a high waisted skirt

Polka Dot Shirt High waisted shirt Chukka Boots

This outfit is just fun. I really like it, mostly because it’s one of the coolest things in a polka dot shirt. The shirt isn’t easy to mix and match with other pieces, but this outfit shows you how to do it just right. Wear a black polka dot shirt with a gray high waist skirt for a youthful and glamorous look. Add a layer by wearing a cardigan. And finally, the chukka boots and socks go perfectly with the outfit. If you like this outfit idea, you might be interested to read our blog post about polka dot outfit ideas.

Wear with Black Tie Waist Shift Dress

black tie waist shift dress chukka boots

Here’s an understated, pretty outfit to wear to work. Wear a black tie shirt dress with black chukka boots. You might want to wear a gray zip coat over it and carry a tonal bag for a more balanced look.

Sweater with a colorful pattern

colorful sweater jeans chukka boots

For a causal and stylish spring or fall look, you can still wear a sweater with a 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 Pointed Top Chukka Boots

As expected, chukka boots look wonderful paired with jeans. If you want to try something different, pair the boots with cargo pants. For a chic casual outfit, you can wear a white lace top and cargo pants with a black leather jacket. The chukka boots go perfectly with cargo pants and the rest of the outfit.

Wear it with a gray windbreaker and skinny jeans

gray windbreaker skinny jeans chukka boots

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

Oversized Printed T-Shirt & Leggings

oversized shirt leggings chukka boots

For a young and energetic casual look, simply wear an oversized printed t-shirt and leggings with chukka boots.

Polka Dot Black Shirt & Black Knit Jumper


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

I hope you enjoy this list of my favorite chukka boot outfit ideas. I’m sure you’ll look great in some of these outfits and you’ll probably like chukka boots as much as other types of boots. Before you go, please read our blog posts for all kinds of outfit ideas.

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