Men’s Casual Boots to wear with Jeans

Written By Bakes

Avid writer on Men's Hair, Grooming, and Lifestyle!

Today we have an abundance of great quality boots to select from different brands and retailers, some boots have been designed to be styled with trousers & then there’s Men’s  Casual Boots to wear with Jeans which we are going to focus on in this article.  

A great pair of boots is not only an investment which will return 10-fold but are also the foundation of your outfit which communicates style, class & masculinity. Therefore, you will need the right men’s casual boots to experience these benefits which is why we have curated a list of the best boots to get you started.


Here are the best Men’s Casual Boots to wear with Jeans


Chukka Boots

chukka boots

The Chukka boot is similar to the Chelsea boot due to the design & structure with the difference being that the Chukka boot features neat secure lacing. Low Block heel, round toe and great design, the chukka boot is a great option for your denim jeans.

The Chukka is mainly described by its ankle height length and minimal eyelets giving it a clean simple finish.

How to wear: For more formal looks select leather chukka boots while reserving suede options for casual entire.


Dessert Boots

boots for men 2021

Dessert boots are a particular kind of Chukka boot which is that there normally formed with a suede fabric.

Both the chukka and dessert feature an ankle height length and minimal eyelets; however, the dessert is made with light leather or light suede and rubber soles. These differences are marketed by brands, so consumers are aware of the differences between the 2.

You can also consider dessert boots being the more informal of the 2 and a great option for casual settings.

How to wear: Pair your dessert boots with a plain t shirt, dark slim jeans and shirt. The most stylish off-duty choice for those still wanting to communicate masculinity and style.


Chelsea Boots

Casual Boots to wear with Jeans

Chelsea boots are one of the most recognizable silhouettes due to the absence of laces, ankle length, rounded toes and low heels.

To quote ourselves

“Today the boot has become a fashion item with credit to the Beatles for its revival in the 60’s. Not to mention most Chelsea boots have elastic gussets making them easy to put on and slip off, a simple feature which ranks them as a favourite amongst men “

How to wear: Visit our How to wear Chelsea boots expert guide which details all the different outfit options, guidelines and practices to avoid.


Monk Strap Boots

Monk Strap Boots

Monk strap boots are sold in multiple variations from 1, 2 or 3 straps while also coming in leather and suede fabrics. 

For men wanting a dapper look thinking about men’s casual boots to wear with Jeans then monk strap boots are your answer. The straps easily capture attention and its sophisticated style is easily a favourite amongst men.

This is a staple piece for men as high-quality monk strap boots have been crafted with premium leather and lining which complements your dapper style.

How to wear: The monk strap boots are best worn with jeans to convey a smart casual look. Pair the leather boots with a shirt, blazer & slim fitted jeans.


The Brogue Boot


Most notable for its distinctive pattern and detailed perforated wingtip ending, the brogue boot will serve its purpose as a stand out casual boot.

The boot features stitched upper, mid, in and out soles resulting in a sturdy look while still comfortable enough for men’s casual outfits.

  • Detailed patterns
  • Solid Construction
  • Laced Up Closure (Some variations have hiking eyelets)
  • Premium Leather

What’s there not to love? 

How to wear: As the nature of the brogue boot is bold and different from other boots its best to treat it in this manner. Opt for colours such as tan or brown to bring even more attention to the boot, finish off with dark navy jeans and a white shirt.


Combat Boots

Combat Boots

The combat boot is a prime example of a utility-based garment designed with soldiers in mind taken from its initially purpose and made into a fashion item.

Much of the appeal surrounding the boot today is due to its military-inspired history, smooth crafted leather, Lace up feature & Leather pull tabs.

The resurgence of the combat boot can also be credited to 90s with brands such as Dr Martens being a focus in fashion.

How to wear: To pull of combat boots the right way you have 2 options, formal or casual. Going for a formal look pair the boots with a shirt, over coat and jeans. For a casual look, jeans and a sweat shirt will just fine.


Lace Up Boots

casual boots for men

Lace up boots as the name suggests are boots which focuses on the lace detail. Some lace up boots will feature brogue patterns, some metallic hardware and other defining features.

The main thing to remember is that lace up boots are designed in a simplistic way ideal for smart or casual outfits.

How to wear: You have the option to lace the boots all the way to the top or have them loosely done. Pair the boots with a plain t shirt, bomber jacket and jeans.


Timberland Boots

boots for men

While were covering different boots to wear and not brands we wanted to throw in the timberland boot as it’s a perfect example of men’s casual boots to wear with Jeans.

To quote ourselves

“Over the years what started as a work boot for construction workers has now turned into a fashion statement through the influence of hip-hop music and street culture. The boot is one of the most recognizable footwear’s worldwide”

While the timberland boot can fall under the lace up or combat boot section we felt this deserved its own section.

How to wear: Visit our How to wear Timberland Boots piece which details Outfit Ideas & guidelines.


Hiking Boots

Men’s Casual Boots to wear with Jeans

For men who enjoy walking long or short distances, hiking boots were created with you in mind.

Waterproof protected, comfortability, durability and improved foot support these boots are different from the rest on the list as it serves the purpose of providing comfort for long distance walking, something that won’t be achieved with Combat boots.

How to wear: As hiking boots are walking boots you’re going to want to be as comfortable as possible. Pair your hiking boots with soft denim jeans or cargo trousers, t shirt, windproof jacket and let the journey begin.


Cap Toe Boots

Men’s Casual Boots to wear with Jeans

Distinguishable by its simple design, minimal details on the toe cap ending, the cap toe boots are a great solution for smart and casual outfits.

It should be worth noting that these boots are the same as brogue boots with the difference in the pattern and detail.

Boots marketed as cap toe boots typically will not feature a design or pattern while Brogue boots will. Nevertheless, these are a great investment if your opting for a simple clean option.

How to style: Pair your cap toe boots with a shirt, trend coat and fitted jeans.


Tips to remember – Men’s Casual Boots

  • Invest in high quality Boots
    A great pair of boots is an investment therefore ensure that you purchase high quality boots which will include premium leather, durable fabrics & comfortable insoles.
  • Care for Boots
    If your boots are leather purchase a simple leather hydration cream. This will ensure that you prevent dry cracks, scratches and stains while increasing your shoes lifetime.
  • Rotation/Options
    Having options not only allows you to increase the lifetime of your boots but will also allow you to pair with multiple different outfits. Start of with different colour boots such as black and navy boots.
  • No Shorts
    Shorts should be reserved for sneakers only and boots for full length pants. The combination of boots and shorts looks disorganized and tacky.


Final Word

Use our curated list of Men’s Casual Boots to wear with Jeans as a reference point and guide to help inform with your future purchasing decisions.

All boots above are perfectly paired with jeans, just ensure the boots are appropriately aligned with the occasion.

We have grouped the boots for you

Long Distance Walking – Hiking Boots

Office/Formal – Monk Strap/Lace Up/Chukka/Cap Toe/Brogue/Chelsea/Most Leather Boots

Casual/Informal – Dessert Boots/Timberlands/Combat Boots/Chelsea/Most Suede Boots


To stay updated on everything happening in  men’s style/lifestyle, street culture & music follow @heartafact on Instagram