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Article: Ways To Wear Boots With Jeans For Men

Ways To Wear Boots With Jeans For Men

Ways To Wear Boots With Jeans For Men


If you are here, you are probably a fashion-forward person with a pair of trendy jeans and sturdy boots in search of inspiration for making these timeless classics rock the streets. It’s hard to imagine a pair that matches better than these two. It may seem that it’s relatively simple to make jeans and boots work together, but due to the numerous variations of shapes and colors, there is a lot of room for missteps. Inaccurate pairing of the models and styles can have some unpleasant consequences, like a disproportionate figure, a sloppy shape, or a styling mismatch. Alas, that possibility discourages a lot of men from experimenting with this particular combination and keeps them away from boots. Sneakers are much easier to wear, after all. But you shouldn’t let it put you off! Powered by some fashion tips and tricks and inspired by a couple of ready-to-go ideas, there is no reason why you couldn’t possibly make a great combo by yourself. In this article, we are going to discover how to wear boots with jeans for men. We will provide you with some can't-fail menswear combinations and share some styling secrets. Black or indigo jeans? Chelsea or Derbies? To tuck or not to tuck? You will find all the answers below!

Fundamentals Of Styling Jeans And Boots

The key to styling jeans with boots is to strike a balance. If you manage to make a well-proportioned fit for your garments, then you've done the most tricky part. Rough military boots will never work with skinny jeans; on the other hand, neat Chelsea boots are not going to match wide-leg bottoms.

Another obvious rule is to always make sure that the shape of your jeans harmonizes with the style of your boots. A slim-fit pair of jeans is a must-have staple; it will suit most of the fashionable combinations. But if your winter boots are a bit too voluminous, you may use a straight or relaxed fit. The sweet spot is the best — not too sleek or too wide, but just in the middle. If your jeans fit on top of your boots, then you’ve coped with the task. We know it might sound a bit complex, but we are here to find out how to style men's boots with jeans in the best way possible. The bigger the challenge, the more satisfying the result.

Hooded down parka FIREBAG

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Light-wash slim-fit jeans

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Choosing the Right Boots

Choosing a pair of boots that will match your style and personal preferences is an effort you have to make if you want your outfit to be exceptional and comfortable. There are different names for boots that resemble the type of lacing, the type of stitching, or the general shape of the boot. Depending on your ideal look and vision, you should consider not only shapes but also the material and color of the footwear. Let's browse through the main names you will encounter while searching for an ideal pair.

Depending on the type of lacing, there are two main styles of boots: Oxfords and Derbies.

  • Oxford boots: a relatively rare option, but worth considering. They feature a closed-lacing system on the shoe, resulting in a tighter shape and a more formal appearance. Balmoral boots are the most common subtype of Oxfords, with the Vamp that goes all around the shoe in a horizontal line.
  • Derby boots: a trendy piece that is currently in full swing of popularity. They feature an open-lacing design, meaning they have a more relaxed and comfortable fit. Usually, they have a rounded toe and a low heel. Chukka and military boots have Derby-type lacing, whereas Brogues can be both Oxford or Derbies.

Depending on the type of styling, there are five main categories of boots that are worth mentioning:

  • Chelsea boots: slim and polished, they have a slight rock-ish vibe with an attitude of subtle rebellion. Featuring elastic side panels for effortless slip-on and off, these boots don’t have any stitching or lacing.
  • Chukka or desert boots: versatile pieces that match well with casual outfits and serve perfectly for everyday outings. They are unlined ankle-high boots with open-lacing and two or three pairs of eyelets.
  • Brogue boots: also called dress boots, are well-known for their decorative perforations, either on the frontal part of the shoe or covering the whole body. Can be both open and closed laced, this type of boots has numerous different variations. They differ in perforation patterns, materials of the skin and sole, stitching shape, color, etc.
  • Jumper or military boots: originally designed for paratroopers, this footwear made its way to the fashion world and became an undeniable trend. Generally featuring calf-length lacing and rigid toe caps, they can also differ in height, materials, hues, etc.
  • Winter boots: they are a little bit off the structure, but even if they are an outsider on this list, they are still our must-haves for the winter season, and we should know what they are about. Generally waterproof and weather-resistant, they have a high side to keep the snow from entering the boot and a rubber sole to keep the water out.

Cargo cotton trousers

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Highneck merino wool sweater

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Choosing the Right Jeans

When it comes to those particular outfits, where jeans and boots have to match and enhance the look, the type of jeans is as important as the type of boots. There are some most popular cuts in jeans, like straight or slim ones, and most common hues, like dark or mid-wash denim. Certainly, there are endless variations when it comes to something as basic and widely used as jeans, but for boots, we should consider some special fits.

As we mentioned before, your jeans shouldn’t be too wide or super skinny. That’s why we recommend having a look at straight and moderately slim cuts. Straight cuts give a relaxed, laid-back ambience to the whole look and work well with Chukkas and winter boots, while slim cuts are perfectly matched with Chelseas, Brogues and some delicate-looking winter boots. The slim cut looks more polished and refined; it adds a formal and elegant hint to the appearance.

As to the hue, the most versatile options are dark- and mid-washed denim, but there are other rare but modish shades. White jeans seem a bit problematic to wear, but they add such a fresh twist to the outfit that you shouldn’t neglect this alternative. Although black jeans are a must. A black slim-fit pair can be the perfect match for your black Chelseas. Complete them with a black tee and a sharp black blazer, and you will create a stylish monochromatic outfit that is, firstly, extremely trendy, and secondly, will suit your business and leisure lifestyle well.

Cuff Or Bust

There are many various styles of cuffing the jeans, but one thing is the most important to follow: they should be cuffed one way or another. Some stylists allow the hem loose in their jeans with boot outfits, but we consider it to be a clumsy way of dressing and highly recommend adding a few turn-ups to the mix. The only remark here is that you shouldn’t make a cuff wide if your height is below average, as it can shorten you generally.

Should You Tuck Pants into Boots or Not

Another crucial question about this specific combination is whether to tuck or not to tuck the jeans into the boots. And the answer is very short: don’t tuck. If you don’t plan to ride a horse or attend a punk concert, cuff your jeans at the hem and wear them over the top. Don’t try to break this rule, or you might end up with a very comical appearance.


Despite the endless variety of hues, both for jeans and boots, there are some combinations that play together better than others. As a rule of thumb, contrasting colors work better than nuanced shades. Try to avoid anything that matches too closely, except for the black hue. Black on black is a stylish monochromatic combination that has stood the test of time. The fashion world loves black looks not only for their versatility but also because of the bold ambient. So if you are about to be at the forefront of fashion, make sure to own some timeless closet staples to build an authentic fashionable outfit.

Check-pattern cashmere sweater

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Classic straight jeans GAGE

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The 6 Best Jeans With Boots Outfits

Now that we have gone through the key points of wearing and styling boots with jeans, we will give you some inspirational outfit ideas, and we hope that they will help you create a unique and impressive look. Let’s dive in!

Brown hiking boots with black classic jeans

A comfortable combination that will be to the point during the cold season features fur-lining leather hiking boots alto bear and a pair of tapered classic jeans adler. Sometimes less equals more, and this simple yet smart combo will add a hint of a laid-back mood to your apparel. Match this ensemble with warm, trendy knitwear and throw a dark-hued, versatile parka on top to stay toasty and chic this winter.

Brown hiking boots with straight-fit jeans

A must-have combination if your winter weather calls for serious protection against the cold features fur-lining leather hiking boots alto bear and straight-fit jeans marty. The rinse-wash denim hue perfectly matches the brown boots’ leather and makes a strong base for a fashionable street style outfit. Pair them with a comfy puffer, toss an oversized scarf over your shoulders, and complete the look with a neat beanie hat.

Basic white T-shirt with dark blue jeans

A combination that is basic and simple serves perfectly for numerous stylings and occasions. A white eagle-embroidered T-shirt in a mix with a pair of dark blue tapered classic jeans adler makes a base for any type of outfit. Try to combine them with dark-colored Chukka or winter boots to make the look sing. When the in-betweens are so casual, footwear and accessories play the most crucial role in elevating the appearance. Choose the classics, and you will never fail.

Hooded bomber jacket with straight jeans

Another timeless ensemble to unwind at the weekend or run your everyday errands combines hooded bomber jacket stagg with relaxed-rise jeans finn. Street style is our favorite to feel comfortable and look chic, and to take this combo to an even higher level, we suggest adding a pair of winter or jumper boots to the picture. Go with the brown or black leather to add some bold vibes, or take a suide variation if you want your look to have a neat and polished appeal.

Quilted wool coat MAJOR

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Leather bomber jacket with slim-fit jeans

This is simply the coolest combination to appear at the forefront of fashion. A black leather bomber jacket paired with light-wash slim-fit jeans can be bent to suit most social settings and seems to be incredibly trendy. Complete the look with black leather Chelseas to create the most dazzling appearance possible, as the black leather of the jacket will definitely support the boot style and enhance the whole ensemble. Add some cool accessories, like sunglasses or a beanie, to take the outfit to another level.

Relaxed roundneck pullover with slim tapered jeans

If you are searching for a versatile outfit to use both for formal and casual events, go for this one. A gray relaxed roundneck pullover mixed with a pair of dark blue slim tapered jeans is a flawless base to build an outstanding look. Slim-fit jeans can be successfully worn with any type of boots: Chelsea, Chukka, Jumpers or winter boots are equally well-matched for this jeans cut. Choose classy black or brown hues for your boots to make the most of this combination. Throw a stylish jacket on top, and you are ready to rock the street!


As you may see now, with a bit of effort and some specific knowledge, you are able to combine and create extraordinary outfits with jeans and boots. Follow some simple rules, add your unique vision, and always remember to cuff your jeans.