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How To Wear Chukka Boots

If you enjoy 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 want to combine 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 t-shirt and leggings

Chukka boots gray t-shirt leggings
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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 just wear an oversized gray t-shirt and leggings with chukka boots for a slightly tougher look than you normally would with a high-top Converse.

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

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

Wear it with a black trench coat and skinny jeans

black trench coat jeans chukka boots
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This is an adorable outfit that is perfect for fall and winter. Team 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. However, you need to be very careful as all the parts need to be in balance or you will look chunky instead.

Wear with a gray slip dress with a sheer overlay

gray slip dress shear overlay chukka boots
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For a nice spring look, you can wear a gray slip dress with a transparent overlay and combine it with color-coordinated chukka boots. This is such a minimalist and chic outfit that is actually quite easy to take off.

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

short t-shirt black leather jacket chukka boots
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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 it with a leather jacket and a gray and white striped scarf

gray white striped scarf chukka boots leather jacket
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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. Just 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.

Dark gray short-sleeved knitted sweater and black mini skirt

Mini skirt gray short-sleeved knitted sweater chukka boots
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Most of the time, chukka boots are combined with socks that either hide in the boots or protrude about an inch over the boots. With this outfit I will show you that they can also be worn with black stockings. For an elegant casual outfit, simply wear a gray short sleeve with a black mini skirt. 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
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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 put together with other pieces, but this outfit shows you how to do it just right. Wear a black polka dot shirt with a gray high-waisted skirt for a young 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 may be interested to read our blog post on dotted dress outfit ideas.

Wear with Black Tie Waist Shift Dress

black tie waist shift dress chukka boots
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Here is a low key lovely outfit that you can wear to work. Wear a black tie-waist shirt dress and black chukka boots. You might want to wear a gray zipper coat over it and carry a color-coordinated bag for a more balanced look.

Sweater with a colorful pattern

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

Wear with Cargo Pants & Black Blazer

Cargo Pants White Pointed Top Chukka Boots
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As expected, chukka boots look wonderful in combination with jeans. If you want to try something different, pair the boots with cargo pants. As 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
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For a really casual look that still looks decent, you can just 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 t-shirt leggings chukka boots
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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 Sweater


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As a business casual work outfit, this shows a beautiful layering technique with which you look intelligent and professional. Just 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 elegant and chic look.

I hope you enjoy this list of my favorite chukka boot outfit ideas. I am sure you will look great with some of these outfits and you will likely like chukka boots as much as you like other types of boots. Before you leave, please read our blog posts for all sorts of outfit ideas.

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