What Pants to Wear with Boots? (We Look At 9 Different Boot Styles)

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What Pants To Wear with Boots?

Pants to wear with boots are a huge topic of discussion, and in this article, we’ll cover the most popular pants to wear with boots. The first question that comes to mind when you think about how to style boots with pants is whether the pants are going to go over the top of the boots or you’re going to show off your beautiful pair of boots.

Trying to find out what pants to wear with boots can be a bit complex. There are so many factors involved, including your own personal style and the type of boot that you are wearing.

You might like wearing boots, but you don’t want to look like you just came from a construction site. So it is a matter of balancing your style and comfort while trying to figure out what pants to wear with boots.

  • Now, if you want a boot that has an already established style, then it’s better if you wear it with a pant that shows off that style. For example, if you own Chelsea boots, then they are supposed to have a slim look so if you pair them with slim-fit chinos, then it will make your legs look even slimmer in comparison.
  • On the other hand, if you do not like how your boots look on their own, then you might want to purchase a pair of chinos or jeans that matches the color of your leather shoes and then lace up your shoes for a casual look. Include different accessories such as rings or belt buckles to add more flair and personality.
  • Another thing that you can do is try out different shoe-leg combinations by matching your pants with different leg-cut styles.

Let’s look at what pants are best for each style of boot…

What Pants To Wear With Chelsea Boots?

The Chelsea boot is a versatile shoe that works perfectly with almost any casual outfit. However, wearing the right pair of pants with them is important in order to achieve a more polished and modern look.

When it comes to trousers, skinny jeans or leggings are the most suitable option. This gives an edgy look which is perfect for the Chelsea boot. Skinny jeans or leggings will also enhance the length of your legs which is essential when you are wearing these boots.

These are probably the most versatile option and will enable you to dress them up or down as necessary. Chinos are more formal while jeans are more casual so if you are unsure what the occasion requires, play it safe and opt for chinos.

The key to wearing jeans with Chelsea boots is wearing slim-fit jeans that hug your body without looking too tight and restrictive.

If you’re not sure what kind of jeans to wear, there are several classic styles that work perfectly with the Chelsea boot.

  1. A pair of dark-wash jeans will look great with Chelsea boots, as will light blue jeans.
  2. The best way to determine what pants will look good with them is to envision yourself wearing them together before you leave the house. Try on different outfits such as a t-shirt, button-down shirt, and other options until you find one that complements each other well.
  3. Another important element in choosing the right pants for Chelsea boots is finding ones that don’t make you look shorter than you actually are.
  4. Make sure not to wear overly baggy or loose-fitting pants, as this tends to shorten your appearance and make the shoes appear even longer than they already are. Loose-fitting pants also tend to make your legs look shorter because there isn’t anything holding them close to your body.

What Pants To Wear With Cowboy Boots?

There are many different kinds of pants that will look good with cowboy boots. The most basic way to match your pants to your cowboy boots is simply by choosing a pair of pants that have some kind of decorative stitching down the sides.

Regardless of what color the stitching is, this will give the appearance that you have a skinny pair of jeans on, even if you don’t.

  1. Jeans: When it comes to jeans, you should stick to darker colors that match better with your boots. Wash them out so they aren’t too stiff and don’t have a lot of extra material at the bottom that would be hanging past your boot tops. If you go with skinny dress pants, you will probably consider them more formal than jeans but less formal than tuxedo pants and as such, wearing them with cowboy boots would be a perfect in-between option.
  2. Casual Pants: Casual pants are an excellent option for men who want to wear cowboy boots because they tend to have more of a tapered leg which will give your legs a more streamlined look and make your legs seem longer. They also typically have less material around the calves and ankles so they will not add any additional bulk to your lower body when you’re wearing your boots.
  3. Chinos: If you’re wearing chinos or khakis that are supposed to look like denim, it’s important not to wear them in a lighter color or they will stick out like a sore thumb when you’re wearing cowboy boots.
  4. Dress Pants: Dress pants are one of the hardest items of clothing for men who want to wear cowboy boots because the fit is often too baggy at the bottom and there is more material around the calves than straight-leg jeans or chinos. Your best bet here is to wear dress pants that have a seam running down the outside of each leg. This means they should be slimmer and more tailored at the ankles.
  5. Tailored Slacks: Tapered and tailored slacks, in a darker color, will make your cowboy boots look even better than they already do. The slack should be form-fitting on your legs so that your boots can stand out more.

What Pants To Wear With Ankle Boots?

The key to wearing ankle boots is all about proportions. If you’ve got a pair of thin or small calves, you can wear skinny jeans with ankle boots or booties! But if you have bigger calves, you may want to avoid pants that are too tight.

Trying to figure out what pants to wear with ankle boots? The rules are simple – keep it slim and narrow. If your lower leg is bigger than your upper leg you may want to avoid pairing ankle boots with wide-legged pants like cargo or chino styles.

As for the length of the pants, if your boots are shorter it’s best to stick with pants that hit right at the top of your boots, but if your boots are taller than 2 inches, you can go with cropped jeans or high-rise pants.

Here are some things to consider when choosing what pants to wear with your ankle boots:

  1. Casual/Street Style – If you’re looking for a casual or street style look, then wear your jeans or colored denim with ankle boots. You can even wear tights underneath your jeans if you wish.
  2. Length – Depending on the length of your legs and what style of jeans you prefer, you’ll want to go with pants that fall about an inch or two above your ankle. Pants that fall just below the ankle will not work as well as pants that fall about an inch or two above it because ankle boots tend to be higher up on your leg than regular shoes and you don’t want to create an awkward look by having one high and one low point on your outfit.
  3. Skinny jeans are great for wearing with ankle boots because they elongate your legs. The skinny fit also works well with ankle boots because it’s nipped in at the ankle. This creates more of an optical illusion that you have longer legs and a more proportionate body frame.
  4. Boot-cut jeans are thick enough to make your legs look longer and slimmer, and they provide comfort as well as style. Boot jeans come in many different styles, so you can find a pair that fits your preference one way or another. They look best with ankle boots or other tall boots because they will balance out your body proportions better than flats would do if paired together.
  5. High-waisted jeans are also good to wear with ankle boots. The high waist part of the pants makes sure that the pants do not fall down. High-waisted pants are perfect for those who want to highlight their legs by covering the upper part of their legs.

What Pants To Wear With Doc Martens?

Docs look great with rolled-up jeans or cuffed skinny’s. The length of the pants does not matter, but the jean size does…the smaller the jean, the smaller the cuff on your Docs. This look is pretty easy to pull off as long as it isn’t too bulky on your ankles or if you’re wearing ankle boots.

Another way to wear Docs with jeans is to cuff them once or twice and leave some room in between the cuff and boot. This is an easy way to show off your style without having something so tight looking.


Dr. Martens Women's Chelsea Boot, Black Nappa, 7


Length of the pants. You have to have enough room in the pants so that you can walk comfortably but if your pants are too long then your Docs will just look weird and like they’re covering up the boots, which defeats the purpose.

  1. Pair of Docs + jeans. The main thing here is to try a slimmer pair of jeans, cropped pants, or a regular pair of jeans that you roll-up. The main thing here is you don’t want to cover up the boot and just let a big chunky toe shoe that doesn’t match anything else in your outfit.
  2. Doc Martens are also great with cropped pants! It gives off a really cool and fresh vibe (if done right). You can either go for shorts, ankle crops, or capris depending on how short you want to go in the summer months!
  3. A third option for styling these shoes is to wear them with regular jeans that are not rolled. This will help you create a more rugged and tomboy style, which is loved by many women who are looking for a change from their everyday girly look.

What Pants To Wear With Combat Boots?

Combat boots are great because they can be paired with almost any type of pants. Whether you’re wearing skinny jeans or leggings, the combat boot look works.

Jeans in general are great to wear with combat boots because they are such a classic item and there are so many different styles and cuts you can choose from.

  1. You can wear your nice dress pants with your newly purchased combat boots. Dress pants are great for work and play. Pair them with a nice blouse and cardigan for work, and for fun pair them with some cute jewelry and a trendy top for date night.
  2. Skinny Jeans – Skinny jeans are one of the most popular types of pants to wear with combat boots. This is a great look for girls who want to look edgy, but still girly at the same time. You can pair your combat boots with just about any shade of blue, black, or red skinny jeans. The only downside to this look is that you’ll have to be very careful how high you wear your pants. If they go too high on your waist, they might not show off your shoes!
  3. Leggings – Leggings are another great option for combat boots. Unlike skinny jeans, leggings usually stop right at the ankle, so you don’t have to worry about showing off too much skin when you wear them with combat boots.
  4. All black – If you’re looking for something basic that goes well with your combat boots, all black is a great choice! This iconic combination can be worn in nearly any situation and will always look stylish. Make sure to select a pair that’s skinny enough to show off your figure and fitted enough to keep things interesting. Bootcut jeans are too loose-fitting to be paired with combat boots; instead, choose straight-leg jeans or cigarette jeans instead.
  5. Navy blue skinny jeans – Another option is navy blue skinny jeans! These pants go great with combat boots because they’re an easy color match. When purchasing these pants, make sure they fit snugly around your hips in order to accentuate your curves! A baggy fit will only make you look frumpy and dull when paired with combat boots; avoid this by choosing the right size.

The key to pulling off this look is wearing your combat boots with the right pants. You want to avoid wearing your combat boots with pants that are too short because it will make your legs look shorter and stumpy.

What Pants To Wear With Hiking Boots?

You can wear pretty much any type of pants you’d normally wear, as long as they aren’t too tight and they’re long enough to cover your knees. Tight pants will restrict your movement and make hiking much harder.

  • First, you must remember not to wear pants that are too heavy. Hiking boots already add a lot of weight to your feet and legs; you don’t need the extra weight from your pants. You want to choose lightweight fabric for this reason. Also, if the material is too thick, it will make your hiking boots feel very hot and uncomfortable.
  • Next, you want to choose plants that do not have a slim fit. If the pants are too tight on your legs, they will restrict blood flow in your legs and cause them to become tired more quickly than they would otherwise. You want to choose jeans or khakis that fit comfortably without being too loose or baggy.

Chinos or cargo pants are good choices because they have a tighter fit without being skin-tight. They’ll be more comfortable than regular jeans, but you can still move around easily in them.

If you’re heading out on an overnight hike, then pack a pair of lightweight sweatpants or hiking pants. They’ll keep you warm at night and also provide a bit of padding for when you’re sitting on the ground.

For summer hiking, cargo shorts make a great choice. Not only do they have plenty of pockets for storing necessities like food and water, but they also allow for cool air movement around your legs and down into your hiking boots.

For spring or fall hikes, consider some lightweight cargo pants. They’re made from lightweight materials that will keep you cool while hiking in warm weather. They also have the same number of pockets as their summer counterparts to store snacks or other belongings while you’re on the trail.

These pants will also work well in winter months if you pair them with thick socks and a warm base layer underneath. It’s important to always dress in layers when heading out during winter.

What Pants To Wear With Chukka Boots?

Tall boots are okay, but they’re not very versatile. Chukkas are the perfect alternative: not too tall, not too short, and with just enough personality to make a statement without being overbearing.

They’re also incredibly comfortable – there’s a reason so many high-end brands make them – and they look good with practically anything.

You should choose pants that match the color of your boots, are the same material (or close), and have similar styling. Slim jeans, chinos, and wool pants all work perfectly well with chukka boots. But if you’re going to wear chukka boots with jeans, make sure they’re not too baggy—you don’t want them to swallow your shoes up.

No matter what color chukka boots you end up buying, you should go with neutral-colored pants. This means that the pant color can be worn with any color of shirt and will always look good.

  1. Trousers can be paired with chukka boots but there are times that it may look better without them. The key to wearing chukkas with trousers is to balance its ruggedness with something more elegant. This means pairing your chukkas with slacks instead of jeans or cotton khakis for a more refined look.
  2. Chinos, cords, or flannel trousers all pair well with chukkas because they contain some form of decoration or pattern to break up the solid color that the chukka creates when worn together.
  3. Cords are perfect if you want to wear chukkas with trousers because they bring out the brown tones in the leather and create a very classic look that will never go out of style.

Here are some things to keep in mind when pairing it with your pants:

  • Keep It Relaxed: Chukka boots are casual and easygoing, so don’t get too fancy with the pants you wear with them. No one wants to see an overly accessorized outfit (not even from the best-dressed man in the room). If you want to wear jeans, hew closer to the classic variety (not a designer or distressed style) and make sure they’re cuffed to show off your shoe without being too crazy about it.
  • Stick With Solid Colors: The chukka boot was designed for outdoor wear, so there’s nothing wrong with wearing it with shorts or other casual styles, but if you’re going to wear your chukkas with pants, stick with solid colors and avoid trendy and bright designs. The last thing you want is a brightly colored plaid shirt showcasing your footwear!

What Pants To Wear With Black Boots?

Black boots are one of the most versatile pieces of footwear a person can own. They match well with jeans, dresses, skirts, and many other outfits. When you wear them with the right pants, it makes you look more stylish and sophisticated.

  1. Tight black pants or leggings look great with these boots.
  2. If you’re going to wear jeans, dark wash skinny jeans look fabulous.
  3. Black velvet pants or even black leather pants will also look amazing when paired with these boots.
  4. Skinny jeans are a great choice for those who want to go for a more sleek and sexy look. This outfit is perfect for nights out in the club or for going to dinner on the weekend. It’s trendy and sexy without being too over the top.

What Pants To Wear With RM Williams Boots?

RM Williams boots are an extremely classy and expensive pair of boots. Trying to find the best pants to wear with them is also a difficult task, as you want to make sure that your pants go well with the boots as well as complement your overall outfit.

Trousers made from fine wool, cotton, and linen blends are ideal for wearing with RM Williams boots. However, you will also want to ensure that they fit properly, which means they should be straight-leg trousers, rather than boot-cut trousers or jeans.

Fortunately, there are quite a few options available and you can wear any combination of pants that you like with your RM Williams boots. The type of pants, the occasion, and the type of boots all come into play when deciding what pants to wear with RM Williams boots.

Trouser Pants

Trouser pants are the most versatile type of pants to wear with RM Williams boots. Some people will look at you funny if you wear them, but they are certainly much more casual than most other types of dress pants. They can be worn in almost any scenario that you would normally wear your RM Williams boots.

Cargo Pockets

A cargo pocket is another type of pant that looks good with RM Williams boots. They are great for warmer climates because they offer much more ventilation than other types of pants. Cargo pockets are also very popular among men because they have so many different uses.

If you want to look really good, then cargo pockets may not be right for you and it might be better to go with another type of pants, like khakis or jeans. Wearing cargo pockets with RM Williams boots will give off a “rough” look


Jeans are one of the most popular pants these days and there is no doubt why people love wearing them – they look good. If you want to pair your RM Williams boot with jeans, make sure that they are blue jeans because they will match perfectly with your boots. You can also try khaki pants as well since they work great with RM Williams as well.

In summary, Boots can give your outfit the kick it needs, but pairing the right pants with them is not as easy as it seems. You want to make sure that the pants aren’t too long or too short. You don’t wanna end up looking like a 90-year-old who forgot to cut their pant legs before they left home.

Here are the different types of pants to wear with boots:

  1. Chinos: Chinos are great when it comes to versatility. They’re comfortable enough for work and they look great with most boots.
  2. Jeans: With jeans, make sure that the fit is snug, but not too tight or you’ll end up looking like a cowboy. If in doubt, go for a darker wash.
  3. Khakis: Khakis are another one of those versatile pieces that look great when combined with just about any type of shoes and boots. Plus, they come in an array of colors and styles, which means that you can make it work for any occasion.

You may also be interested in… Boots Similar to Iron RangerWhat Pants to Wear Hiking? and What to Wear with Camo Pants?