What Kind of Men’s Jeans to Wear with Chukka Boots

Men's Jeans to Wear with Chukka BootsPhoto by Karolina Grabowska


It’s almost impossible not to find a pair of chukka boots in a stylish gentleman’s shoe rack. But more important than owning these elegant pair of boots is knowing how to style them.

There are different ways to style your chukka boots and different kinds of trousers to match them with, but if jeans are your thing we can help you look your best with minimal effort.

What kind of jeans to wear with chukka boots? Loose fit, relaxed fit, tapered fit, slim fit, skinny fit and narrow fit jeans are some of the best jeans to wear with chukka boots.

To the newly inducted gentleman, you may be asking:

What Kind of Footwear are Chukka Boots?

Chukka boots are casual shoes. You can use them for your everyday wear. But this doesn’t mean they can’t serve other dress codes. They can. They can be used as dress shoes, smart casual and business casual.

We’ll soon see how we can style them to achieve a business casual and smart-casual looks.

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Types of Jeans for Men

There are different ways to categorize jeans for men, but in this sub-section we’re going to categorize them according to their fit.

1. Loose fit

These jeans fit loosely from the butt, down to your ankles. They don’t stick to any part of your legs, not even your thighs.

I love loose fit jeans because there’s room for enough air to flow around my legs, and I don’t feel restricted.

2. Skinny fit jeans

These are the opposite of loose jeans. They fit tightly right from the waist to the ankle.

Skinny jeans have  become fashion statements over the years. But here’s the thing, skinny jeans have negative health conditions. They can cause urinary tract infections, bladder weakness, twisted testicles, and more.

So we advise you wore them sparingly.

3. Slim fit jeans

Slim fit jeans are close fitting without being tight like skinny jeans. They have more space around the thighs (when compared with skinny jeans), with tapered leg opening.

4. Relaxed fit

Here’s the midpoint between loose fit and skinny fit jeans. Relaxed fit jeans are loose, but not the baggy kinda loose as is the case with loose jeans.

They give just the right fitting.

5. Tapered fit

Tapered jeans fit loosely around the waist and thigh, but narrows towards the ankle where they are tight.

6. Narrow fit

Narrow jeans are loose from the waist to the knees, then narrow from the knees down.

How to Style Chukka Boots with Jeans

Our style experts tell us we can style chukka boots with jeans and create 3 kinds of outfit:

  1. Business casual
  2. Smart casual and
  3. Casual

In this subsection, we’ll see how to achieve each of the looks stated above.

Business casual

For this look, go for narrow fit jeans or relaxed jeans. Choose a plain long sleeve botton-down shirt and pair with a casual blazer.

We recommend wearing black, brown, grey or blue jeans. These are widely recognized as business casual colours.

Of course, you’ll need to tuck in. Your shoes, belt and wristwatch should match in colour.

Smart Casual

Our jeans recommendations for this look are loose, narrow or relaxed fit jeans. Any of these can be worn with a polo or short sleeve button-up shirt.

To look smart, wear your shirt or polo with a jacket. You should tuck in as well.

On days when you need to wear a sweater, wear a button-down shirt (instead of a polo). Let the collars of the shirt rest on the sweater, not under. You’ll look cool.

Remember to take pictures for the gram


There are less rules for this. Let your imaginations come alive.

For a casual look, you can wear any trousers fit of your choice with a crew neck T-shirt and denim jacket.

Factors to Consider When Styling Jeans with Chukka Boots

1. Colour

A colour-matching trouser with shoes is a task of its own. The safest colours for chukka shoes are black and brown, while the safest colours for trousers are black and blue. But there are a plethora of other colours you can rock, so we’re not going to tell you to stick to wearing the same color of shoes or trousers daily.

Check out our table below for some colors you can pair.

Trouser Chukka boots
Black Grey, navy
Navy Burgundy, grey, navy, white
Blue Beige, burgundy, grey, orange
Light grey Burgundy, navy, white, purple
Dark grey/ charcoal Burgundy, grey, navy
Brown Burgundy, grey, navy
Tan Beige, burgundy, green, navy
Olive Beige, burgundy, white
White Beige, burgundy, grey, navy, orange
Beige Burgundy, green, navy, orange

2. Season/ weather

When the weather is warm or hot, consider wearing loose fit trousers. You need all the air you can get even while wearing trousers. Skinny fit trousers come in handy when the weather is cold. They are tight-fitting, so there’s no room for cold breeze to harass you.


3. Occasion

What event would you be going for?

Tapered jeans and skinny fit jeans could be appropriate for a walk or hang out with friends or anything not formal. But loose and relaxed fit jeans, are better suited for business casual.

4. Body type

There are 3 body types: endomorph, ectomorph and mesomorph.

Ectomorphs are leaner and skinnier. If you fall here, wear slim fit jeans. Slim fit jeans enunciate your curves, without highlighting your lean frame.

Mesomorphs are broader and muscular. A relaxed jeans will look good on you if you fall here.

Endomorphs are stockier and chubbier. They are big-boned. Our jean recommendation? Loose fit jeans.

How to Measure Yourself for Jeans

Last Christmas, I had a date with my crush. So I walked into a store and bought myself a pair of really nice jeans. I already had a thousand and one ideas on how I’d style my new jeans.

Long story short, those jeans didn’t fit. They were smaller. I felt really sad because those jeans were my passport to securing a spot in her memory.

To avoid a repeat of such, I had to learn how to choose the right jeans size. To do this, I had to learn how to measure myself for jeans.

Let me teach you.

Measurements to take

Waist: Mark the point you’ll like your waistband to lie. It could be a little above your waist, on your waist or below your waist

Inseam: This is the distance between your crotch and the hem of your trousers. Measure the inseam of a trouser that gives you the fitting you like.

Hips: To measure, wrap the tape around the widest part of your hips

Thigh: Wrap your tape around the fullest part of your upper leg to measure

Rise: measure the distance between the waistband to the fork of the trousers.

Compare your measurements with the size chart provided by your seller when buying your next pair of jeans.

How to Care for Your Jeans

Spot clean

When you notice a stain on your jean trousers, clean the spot(s) with sponge and mild washing soap then air to dry.

But where spot-cleaning won’t be enough, wash them.

The Best Way to Wash Jeans

  1. Turn your jeans inside out before putting them in the washing machine. Use cold water and mild detergent.

If you’ll be hand-washing, soak the jeans for about 15 – 20 minutes before washing. This will break down the dirt.

Turning your jeans inside out, using cold water and mild detergent helps your jeans retain their colour.

  1. Rinse

While rinsing, don’t wring the jeans! Just fold them up and press firmly on them to release excess water.

  1. Air dry

You can air dry by laying them flat or hanging them on a line.

How to care for your Chukka Boots

Chukka boots are usually made with leather or suede.

How to Care for Suede Chukka Boots

Do the following to remove stains or scuffs:

  1. Use a suede brush or cloth to brush off dirt
  2. Mix water and vinegar in the ratio 2 : 1
  3. Dampen a clean cloth with this solution then wipe the shoes gently
  4. Leave to dry

Use suede protector to restore colour and protect from dirt.

Alternatively, after using a suede brush to brush off dirts,

– Generously spray a suede cleaner on your boots.

– Brush again

– Let the boots dry for about an hour

– Use the rubber part of your brush to erase stains

– Then spray a suede protector and leave to dry for about 30 minutes.

How to care for Leather Chukka Boots

To remove dirt from leather boots, you’ll need a horsetail brush, saddle soap and a damp rag.

– Brush off loose stains with the horsehair brush

– Use the damp rag over your saddle soap to create a light lather

– Rub the lather over the boots and leave to dry

For your leather boots to last longer, you need to ‘lock’ them so it becomes water-  and crack-resistant.

You do this by conditioning the boots with a good leather conditioner or balm.

You should also polish periodically with quality polish to maintain the shine of the boots. Please, don’t use liquid polish for leather boots. They reduce the quality of the boots.

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