Can You Wear Cropped Trousers with Ankle Boots? (10 Ways To Style This Look)

Can You Wear Cropped Trousers with Ankle Boots?

Cropped trousers are the perfect transitional piece to take you through the seasons. They’re great for layering at this time of year, and when paired with boots, they look effortlessly polished.

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Cropped trousers with ankle boots are a great combination because they show off the boots and make your legs look longer. They also look great with a range of accessories from scarves to backpacks and everything in between.

You are free to choose any style you want, starting from boyfriends and skinnies to flares and wide-legs. In other words saying, every pair of trousers will look awesome with ankle boots.

Cropped trousers are great because they come in all shapes, colors, and lengths. Whether they have a cuff or are straight-legged, there are always ways to wear them off-season. Even though they may not seem like a fall or winter trend, they can definitely be worn in the colder months if styled correctly (and on those warmer-than-usual days).

However, if you don’t choose the right style and length of boot, the look can fall flat. To avoid any fashion faux pas, we’ve put together 10 ways to wear cropped trousers with ankle boots that will help you nail this tricky trend.


10 Ways To Wear Cropped Trousers with Ankle Boots

Cropped trousers are the perfect match for ankle boots, as they show off your shoes and make you look taller than you really are. There are many different ways that you can wear this combination of clothing so let’s take a look at some of them…

1. High-Waisted

The high-waisted cropped trousers are a timeless wardrobe piece for women. They are versatile, slimming and the best thing is that they go with almost everything in your closet.

High-waisted trousers and ankle boots are a match made in heaven. The look is super-flattering and elongates your legs, which is always a good thing. You can wear them with a cropped or full-length pair of trousers – both look great.

A high-waisted slim-fit cropped trouser is a flattering and comfortable option for your everyday wear. For a more casual look, pair them with a chunky Chelsea boot but be sure to tuck in your top so as not to cover up the waistband. If you opt for a heeled Chelsea boot, it’ll elongate your legs and lengthen your frame without looking too dressy.

High-waisted cropped trousers can be worn with ankle boots to create a stylish and chic look. No matter the type of ankle boots you are wearing; be it heeled or flat, wedge or stacked heel, sneakers or booties, they can pair well with high-waisted cropped trousers.

2. Ankle Grazers

To create an on-trend look for the season ahead, pull on your favorite ankle grazers and team them with a pair of chunky heeled ankle boots. This season’s ankle boot trends will see you spoilt for choice when it comes to shoe options, but I’m particularly loving the chunky heeled boot style.

Ankle grazer trousers are cut at just the right spot on your ankle so they sit perfectly with all styles of ankle boots — from classic Chelsea boots to western-inspired cowboy boots — so they’re a great choice when you have several different styles in your closet. The loose fit makes them a comfortable option for wearing all day long.

What makes them so special is that they are several inches shorter than regular trousers. They are very flattering, particularly if you’re short. They give the illusion of a longer leg and they elongate your height, making you look taller and slimmer.

3. Skinny

If you want to underline your femininity and keep things boho-inspired, then I highly recommend wearing skinny cropped jeans completed with lace-up ankle boots in brown leather color. You can always add a touch of glamour by wearing a cool fedora hat in black color and an oversized statement necklace.

Skinny-fit cropped trousers are ideal for complementing ankle boots with a feminine heel as they create an uninterrupted line from hip to ankle, which elongates the leg and lengthens the frame. This will give you an ultra-chic look that’s perfect for work or weekend wear. Keep the rest of your outfit simple with a plain white shirt.

The key is to pick a pair of ankle boots that are sleek and minimalist in design – no chunky platforms here, please!

4. Baggy

Baggy cropped trousers are the most comfortable and cool items you can choose to wear on these hot summer days. Today’s fashion is all about comfort and functionality, that’s why you don’t need to worry about what to wear, as everything will look awesome on you.

A super-relaxed, baggy trouser is a fun option for cropped trousers — pair them with your favorite chunky ankle boots for an effortless look.

If you have short legs and a small frame, wearing baggy cropped trousers with ankle boots can be a challenge due to the fact that they make your legs look even shorter.

In order to avoid this, you should combine them with ankle boots that have heels or chunky heels in order to add height. Also, it would be better if your trousers were cropped at the ankles so that your proportion was lengthened.

5. Sporty

A pair of sporty cropped trousers works perfectly with a trainer boot — they come in a range of colors and materials so you can really have some fun with this look. A bright white top will really make the trousers pop.

The sporty version is ideal for athletic bodies, as well as for women who want to add some eye-catching details to their everyday outfits.

To make the look work, wear sporty cropped trousers with a thick fabric and pair them with chunky ankle boots. Ankle boots with a heavy sole are perfect for adding some edge to a feminine shape, so this is a great look for anyone who wants to avoid looking overly girly.

6. Paper Bag Waist

A paper bag waist trouser looks great when worn with a slim ankle boot — it provides a perfect balance between looseness and sleekness. Consider pairing this look with a mid-heel for a truly classy look.

  1. Wearing cropped trousers with ankle boots looks best when your ankles are showing. So, opt for a pair of paper bag waist cropped trousers that are 2-3 inches shorter than your favorite ankle boot. This creates the perfect hemline and shows off your ankles.
  2. Paper bag waist cropped trousers with a fuller cut leg look best teamed with a pointed toe ankle boot, as the two shapes work well together.
  3. To create a high-end look, wear your paper bag waist cropped trousers with a pair of black suede ankle boots and team with a silk blouse and tailored blazer. Finish the look with oversized sunglasses and a designer handbag for added luxe appeal.

7. Classic

Cropped trousers look so chic and polished when they are styled with ankle boots or booties. If you are a fan of classic looks, then I recommend trying on ankle boots in black color teamed with cropped pants in a black hue.

If it’s too monotonous for you, then I suggest adding a pop of color via a colored bag or blazer. For instance, you can go for a red handbag and a printed scarf.

A simple, classic look with your favorite cropped trousers, a crisp white tee, and a pair of ankle boots. The perfect outfit for running errands or meeting friends for lunch.

8. Boyfriend

Boyfriend cropped trousers have been a big trend for a little while now, but this season the look has been updated with ankle boots.

A boyfriend trouser looks amazing paired with a chunky heel ankle boot — the loose fabric is casual yet still very chic. Try cuffing your trousers slightly to create a more polished look.

This combination is great for those days when it’s too warm for jeans but too cold to go bare-legged. Cropped trousers provide a little more coverage than shorts, but because they end above the ankle you don’t get that suffocating feeling of your calves being enclosed in fabric.

Ankle boots work well with cropped trousers as they stop before your foot – if you wore them over the top there would just be too much material!

9. Straight

This might seem like the obvious option, but straight-leg trousers and leather Chelsea boots are an absolute classic. A black leather jacket will keep things edgy while still allowing you to feel feminine and chic.

The key to wearing straight-leg trousers cropped trousers with Ankle Boots is to make sure that your trousers sit just above the top of your ankle boot, so you can see a glimpse of skin between the two items.

If you’re wearing skinny jeans, we’d recommend sticking to a simple pair of ankle boots without laces or buckles. As for colors, black works well with blue and black denim. For more color and character, opt for tan or brown.

If you would prefer something smarter than skinny jeans but still want to wear straight-leg trousers cropped trousers with Ankle Boots, then consider opting for a chino instead, which is just another name for a trouser that has less structure than a suit trouser. You can wear chinos in any color you like but if you want to play it safe then stick to neutral colors such as beige or grey.

What about cropped chino trousers?

A great alternative to jeans, a pair of chinos are the perfect option for cropped trousers — pair with your favorite ankle boots, an oversized sweater and you’re good to go! A super-cute outfit that’s both comfortable and stylish at the same time — what more could you ask for?

The chinos-with-ankle-boots look is a perfect and easy way to pull off the chino pants trend. Whether you’re looking for a polished and professional look or a more casual ensemble for a day in the office, this is one outfit that would work as both.

For an elegant look, wear your straight-leg pants cropped pants with ankle boots and an oversized blazer or poncho-style coat.

10. Tailored

If you are into office-style outfits, then you might like to try on cropped trousers in beige color worn underneath a classic tailored blazer in navy color teamed with a white blouse. Complete this look by adding gold jewelry, a black leather handbag, and knee boots.

A tailored pair of cropped trousers will look ultra-sleek when worn with heeled ankle boots — if you’re going for a corporate look, try this combo. For an extra touch of polish, wear your hair up or add a statement necklace.


In summary, Cropped trousers are an incredibly easy way to stay comfortable on your commute, but after that, it can be tricky to know how to wear them. Luckily, the combination of cropped trousers and ankle boots is one that’s easy to pull off and will keep you looking stylish all day through.

You may also be interested in… What Are Ariat Boots Good For? (Working, Riding, Night Out) and Why Do Your Boots Squeak When You Walk? 11 Reasons Why Boots Squeak