Can You Wear Boots with Tapered Trousers? (8 Boot Options For Tapered Trousers)

Can You Wear Boots with Tapered Trousers?

Tapered trousers are one of the most formal trouser shapes. They taper into a narrow ankle and usually have no break – that’s when the fabric sits on your shoe.

Boots are less formal than shoes. So if we were to apply the rules of formality, it would seem like we shouldn’t wear boots with tapered trousers. But in truth, it’s a bit more complicated than that.

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The first thing to consider is the style of boot. A classic brogue or Derby boot is going to be completely at home with tapered trousers. So will a Jodhpur boot or anything else that’s relatively sleek and understated. If it has elaborate detailing, buckles, or plenty of decorative stitching, then it might feel too rugged for tapered pants and a tailored outfit.

The second consideration is the material of the boot. A smooth leather will always be more formal than something suede or nubuck. You can wear brown suede boots with tapered chinos, but they’re not quite as dressy as black calfskin boots with dark wool trousers.

8 Boot Styles That Look Good With Tapered Trousers

If you love a clean, fitted look, then you’ll love tapered trousers. These pants hug your legs from waist to ankle and look great when paired with a crisp white oxford or a classic T-shirt. They’re a polished alternative to skinny jeans and are comfortable enough for all-day wear.

If you’re looking for shoes to go with tapered trousers, boots are your best option, but not just any boots will do. You want something that looks sleek and sophisticated, not clunky or too casual. A good pair of boots should complement the streamlined shape of tapered trousers rather than competing with them or overwhelming your overall silhouette.

If you’re in the market for some new footwear, we’ve rounded up eight options that will look amazing with your tapered trousers.

1. Ankle Boots

Ankle Boots are by far the most popular option for styling tapered trousers because they’re so versatile and easy to wear. The universal appeal of these boots is that they are a transitional piece that can be worn in any season – and even on nights out in the summer months with cropped pants.

Ankle Boots will suit almost every type of trouser – from jeans to chinos or tailored pants. Due to their simplicity, they are also a good choice if you’re planning to wear two or more colors with your outfit.

When wearing ankle boots with tapered trousers it’s important that they are not too long in length as this will result in your legs appearing shorter and stockier than they actually are. To help achieve the best results try to select a pair that do not come above your ankle bone (this is the most flattering length).

wearing ankle booties with tapered trousers because they add a feminine touch that contrasts well with the masculine tailoring of menswear-inspired trousers. This look is perfect if you want to create an androgynous outfit that still has a feminine touch.

To create this look, pair your tapered trousers with ankle boots in either the same color or in a contrasting shade.

2. Chelsea Boots

Chelsea boots (Available at Amazon) are another great option for styling tapered trousers with their low profile and sleek silhouette they will dress up any casual outfit. They have a very clean line, which works well for skinny or tapered fit pants. This is an excellent choice when you want to upgrade your casual looks, but don’t want to wear dress shoes or boots.

These are sleek and easy to slip on and off. They’re perfect for wearing trousers because they’re made to be worn with them. That said, they can dress an outfit up quite substantially, so be sure to pair them with more casual attire instead of suits or blazers.

Chelsea boots go well with jeans as well as chinos and tapered trousers. They’re not the most hard-wearing type of boot out there (and certainly not the best looking), but they’re very comfortable and easy to wear with almost anything in your wardrobe.

It’s also a good idea to wear your Chelsea boots with a sports coat or blazer for a sleek and sophisticated look. They pair especially well with tweed jackets and trench coats.

3. Chukka Boots

Chukka boots (Available at Amazon) are another good choice if you want a dressier look. The shorter ankle height of chukkas makes them less formal than knee-high boots, but they’re still smart enough to wear with suits and other tailored clothing. For this reason, they’re a popular choice for business casual wear or office environments where jeans aren’t appropriate but dress shoes may be overkill.

One drawback to chukka boots is that they usually have open lacing, which can make the fit looser than most other styles. This isn’t necessarily a bad thing, though, so if you prefer more relaxed footwear, keep this in mind.

As for color, brown is the standard for chukkas because it’s a bit more casual than black and goes well with earth tones like olive green and tan or khaki trousers. If you’re just starting out with chukkas, you’ll probably want to stick with a darker shade of brown to be on the safe side — something in the range of dark brown to espresso or even black if they’re going to get a lot of wear.

4. Knee High Boots

Another popular boot style to wear with tapered trousers is the knee-high boot (Available at Amazon). This boot looks great when paired with skinny, peg-leg, or cigarette trousers that are tapered but not too tight in the calf area.

Depending on your personal style and the look you’re striving for, you can choose from a variety of heel heights, including flat, kitten heel, mid-heel, and stiletto. These boots can be worn with a variety of tops as well, including sweaters, blouses, and button-down shirts.

Knee-high boots are typically designed with a slimmer cut than mid-calf boots, so they look great with tapered pants because the proportions will be well balanced.


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If you opt for a pair of knee-high boots in a neutral shade like black or brown, you’ll create an elongating effect to your legs; so you’ll look taller and leaner. The only drawback to this type of boot is that they may appear too bulky around the ankles if they fit too loosely.

To avoid this problem, choose either a flat pair of boots that fit snugly around your ankles, or select a pair in stretch fabric that hugs your skin.

If you have thicker calves, avoid knee-high boots that feature a lot of detailing at the top, such as heavy embellishments and ankle straps. These details bring attention to your calf area and will make them appear larger. Instead, choose a simpler design that features smooth leather and a slim silhouette.

5. Mid Calf Boots

Mid Calf Boots (Available at Amazon) are good to wear with tapered trousers because they have a sleek and polished look that compliments the style of the tapered trouser. They have a classic look that flatters the leg, making it great for men who are taller.

The color of your ankle boots can be black or any dark neutral color like dark brown or grey. If you want to wear a different color, ensure that it’s a darker version of your trouser color. For example, if you’re wearing navy tapered trousers, then you can wear dark blue mid-calf boots.

Mid Calf Boots are good to wear with tapered trousers because they will provide a nice balance between the volume of the pants and a shoe that is too small. The shaft on mid-calf boots is larger than that of ankle boots but smaller than knee-high boots. Mid-calf boots are especially great for winter, as they will cover your calves and keep you warm.

6. Flat Boots

Flat boots (Available at Amazon) go well with tapered trousers, especially when they are paired with a slim-fitting jacket. A pair of flat boots can add an elegant touch to the outfit while also looking quite contemporary and stylish.

Flat boots come in several different types, including Oxford and brogue styles. Brogues are particularly effective for adding some flair to an outfit that includes tapered trousers because their signature perforations create visual interest without detracting from the overall neatness of the look.

Boots in black, dark brown, or another dark color can be worn with most forms of dressy attire, including suits, blazers, vests, sweaters, and button-down shirts. Flat boots can also be a good choice for casual outfits such as jeans and T-shirts. If you’re wearing a shirt in a plain color such as white or blue, choose boots in a bold color like red or yellow to add eye-catching appeal to your outfit.

7. Desert Boots

Desert Boots (Available at Amazon) look good with tapered trousers because they are slim in design and they have rubber soles that provide traction when walking on uneven surfaces.

They also come in different colors like brown, green, or black so they will go well with any shade of pants or jeans! You can choose from leather or suede material depending on what type of finish you want for your boots.

With their simple construction and lack of embellishment, Desert Boots can be paired with almost any outfit. But they look particularly good with tapered trousers, as the casual styling of the boots provides a nice counterpoint to the more formal silhouette of the trousers.

8. Derby Boots

Derby boots, also known as Blucher boots, are ankle-high boots made from leather and often have brogue details. Derby boots are the most formal type of boot you can wear with tapered trousers, which is why they’re the favorite choice of sartorialists in their high-end tailoring. If you want to look slick and trim, you can’t go wrong with a pair of derby boots.

With their cap toe and sleek, unadorned profile, they have the same kind of clean lines as Oxfords and other dress shoes, which means they’ll coordinate well with almost any suit.

They’re also extremely comfortable once you break them in, so you’ll be able to wear them all day long without discomfort.


In summary, Tapered trousers are a standout piece this season, and what better way to wear them than with a pair of boots? The key to nailing the look is making sure the length of your trousers and boots complement each other.

For example, if you’re wearing slim-fit chinos that end at the ankle, then it’s recommended to wear a chukka boot or Chelsea boot that has an ankle height.

You may also be interested in… What Can You Wear With Timberlands? and What Boots to Wear with Skinny Jeans?