How to Wear Chukka Boots

Last Updated: December 3, 2021 References

Chukka boots are a classic and timeless type of shoe, but you might be wondering how to wear them and what kind of outfits chukka boots go with. These ankle-length boots usually have thin laces and tend to be made from suede or leather. Wear the chukka boots with a pair of long pants and a shirt. Chukka boots are incredibly versatile and can be dressed up or down depending on what you wear them with. Be creative and express your unique style!

Method 1

Method 1 of 3:

Pairing Chukka Boots with Pants

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Wear your boots with jeans if you want to create a streetwear outfit. Chukka boots look best with slim or skinny fit jeans as they match the tailored style of the boots. Choose a pair of light denim jeans for a more casual street look, or opt for a darker shade of denim if you want a slightly dressier streetwear look. If you want an on-trend option, pair the boots with a pair of ripped jeans.^{[1]
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Expert Source

Kathi Burns, CPO®
Fashion Stylist
Expert Interview. 31 December 2019.}
- A pair of light grey chukka boots, pale blue skinny jeans, and a white linen t-shirt would make a great outfit for going out to brunch with friends.
- If you don't like jeans, opt for chinos or linen pants instead.
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Pair the boots with dress pants if you want to style a formal look. Chukka boots are the perfect way to modernize a classic suit or formal outfit. Wear the boots with dress pants or suit pants and put on a long sleeved shirt and blazer to create a sharp and on-trend outfit.^{[2]
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- Wear dark colored chukka boots to achieve a dressier look.
- Avoid rolling up your dress pants. Simply let them hang over your boots.
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Rock drawstring pants with your boots if you want a casual outfit. The pants you wear with your chukka boots will play a big part in dictating how formal your outfit looks. Choose a pair of casual pants, such as drawstring trousers or chinos, to achieve a comfy yet stylish look that is perfect for casual outings.^{[3]
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- Wear a loose fitting t-shirt to complete this casual outfit.
- Opt for a light colored chukka boot to complement this casual look.
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Roll up your jeans if you want to draw extra attention to your boots. This on-trend style is an easy way to change up your look and draw the focus down to your shoes. Fold your jeans up to your ankle bone and leave your ankles bare. Wear a pair of ankle socks to keep your chukka boots smelling nice and fresh.^{[4]
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- This option works best with jeans and chinos. Avoid folding up suit pants as this makes the outfit look less formal.
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Wear shorts to dress up a summer outfit. Chukka boots are a great way to make a simple summer outfit look a little smarter. Wear a pair of ankle socks under your chukka boots so that your socks can't be seen. Throw on your favorite pair of cotton or denim shorts, pop on a shirt, and you are ready to go.^{[5]
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- Avoid wearing board shorts with chukka boots as this looks a little goofy.
- Navy blue chukka boots, dark denim shorts, and a white linen shirt would be a great outfit for attending a low-key summer birthday party.

Method 2

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Choosing Shirts to Wear with Chukka Boots

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Wear a long-sleeved dress shirt if you want to create a smart look. Long-sleeves shirts are a great way to make a simple outfit look a little more formal and have the added benefit of providing extra warmth on chilly evenings. If you want a smart but relaxed style, let your shirt hang loose. If you are looking for a more formal option, tuck your shirt into your pants. Complete the outfit with your favorite pair of chukka boots.^{[6]
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- Vary your outfits with different textured shirts. Experiment with cotton, linen, and silk.
- Iron your shirt before you wear it to make it look extra sharp.
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Opt for a t-shirt if you want a more relaxed look. Short-sleeved t-shirts are much more comfortable on a warm day and give your outfit a more laid-back feel. Wear your favorite pair of chukkas, a pair of casual pants, and throw on a t-shirt. If you want a minimalistic look, wear a plain t-shirt, and if you want a more creative look, choose a patterned t-shirt.^{[7]
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- Let your shirt hang loose for this relaxed and casual style.
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Pick a short-sleeved button-up shirt if you want a smart casual option. This style works well for occasions where you want to look smart but not too dressed up. If you want to create a hipster look, do up your top button. If you're going for a more relaxed look, leave it undone.^{[8]
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- Pick a shirt with a subtle pattern if you want to add flair to your outfit.
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Throw on a sweater if you want to look sharp. Sweaters are the perfect choice for cold winter days. They also help to make any outfit look extra smart. If you're heading to the office, opt for a plain sweater made from a wool, such as cashmere or merino. If you're looking for a sharp but casual option, pick a cotton knit or polyester sweater to complete your outfit.^{[9]
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Method 3

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Picking Chukka Boots

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Pick a pair of leather chukka's if you want a durable and versatile boot. Leather chukka boots look great with both formal and casual outfits, making them a versatile choice. Leather is incredibly durable and lasts longer than suede. The material doesn't tend to show marks which helps these boots to look new for longer.^{[10]
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- Use a waterproofing leather spray to protect your boots from moisture.
- If your boots show any signs of wear and tear, polish them with a shoe polish that matches the color of your boots.^{[11]
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Choose a pair of suede boots if you want a stylish and casual option. These boots are very on-trend, making them a great choice if you want to create a stylish outfit. This material is best suited for casual or business-casual outings rather than formal occasions.^{[12]
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- Suede boots can be marked by water. Use a suede waterproofing spray to keep them looking their best.
- One of the added benefits of suede is that it molds to the shape of your feet making the boots really comfortable.
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Pick a darker shade if you want to create a formal look. Darker colors are a great way to make an outfit look classier. Pick a black, dark grey, or navy shoe if you want to wear it to a formal occasion. These shades work well with almost any colors, making them a versatile choice.^{[13]
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- The added benefit of these colors is that they don't tend to show the dirt.
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Opt for a lighter shade if you want a more casual option. Lighter colors tend to create a more casual and laid back look. Pick chukka boots in creams, tans, light-browns, and light-greys. These colours are versatile choices as they work well with most colours.^{[14]
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- These colors get dirty quickly, so use a suede protectant spray to help stop the shoes from getting stained.
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Look for shoes that fit snugly around your ankle. A shoe that fits you well will look sharp and tailored. Slip your foot into the boot and check that it covers your ankle. A snug, but not uncomfortably tight, fit will look flattering on your foot and be easy to move around in.^{[15]
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Expert Source

Kathi Burns, CPO®
Fashion Stylist
Expert Interview. 31 December 2019.}
- If the shoe feels a bit loose, try tightening the laces. If it is still too loose, try on some other brands of shoes to find a tighter fit.