How To Wear Men’s Dress Boots with Jeans

Wearing a pair of casual jeans with the more formal dress boot might seem like a tricky thing to achieve but fret not – we’ve compiled a list of the best dress boots to team with denim, along with how to wear them.

Men’s Chukka Boots

Let’s start with the basics. The Chukka boot (also known as the desert boot) was introduced in WWII by British soldier Nathan Clark as a lightweight alternative to the original military boots. Once the war ended, Nathan Clark presented his design to his father, who also happened to run a shoe company, and eventually became the Clarks retailer we all know today.

How To Wear Chukka Boots

Chukka boots for men come in a whole range of colours, each one providing a slightly different vibe and style to your outfit. Black desert boots go with most things, so if you’re looking for something that doesn’t require colour coordination, they might be a good choice.

If however you prefer a warmer look, then a pair of brown chukka boots will help to give a softer finish. Chukka boots for men tend to be made from a light suede, so they’ll give off a more relaxed look than other boots. Match them with a pair of blue jeans and a light top, like a simple white T-shirt, for a classic, flattering style.

Men’s Chelsea Boots

If you’re looking for dress boots to wear with a suit then Chelsea boots are a safe option. Their smooth, slip on design gives them an elegant finish that’s perfect for complementing, rather than overpowering, a classic suit. Their close fit also ensures that your feet are kept secure and protected, and makes them perfect insulated dress shoes. 

Men’s Chelsea boots can be paired with an endless array of outfits, smartening up a casual jeans and T-shirt combination, or adding an unconventional twist to a formal suit. Because of their simplicity, they’re generally ideal for a range of looks, and if you choose a pair in a dark brown or black, they’ll go with most colour combinations.

How To Wear Chelsea Boots

While traditionally made from leather, men’s suede Chelsea boots are now a popular design, with the matte texture of the suede helping to tone down the overall look of the boots. Men’s suede boots are therefore a good choice if you’re looking for something to wear with a casual outfit and give a less polished finish.

Of course, leather Chelsea boots are a classic for a reason, and if you want to create a more striking look, then a pair of high shine Chelsea boots will help with this. A pair of black skinny fit jeans with a muted top paired with them will help to emphasise the shine of the boots without creating too much of a contrast.