How to Wear Cropped Pants for Men

Pants, trousers, and any type of bottoms seem to evolve more and more as the years go by. Different lengths, fits, styles, and colors are continuously innovated into modern styles. Things that were deemed to be unacceptable at some times, due to social norms, are now seen everywhere. Different ways to wear them also pop up here and there. One of the more stylish pieces that we have all grown to love are cropped pants for men. These pants are now a style staple that every man should consider having in their wardrobe.

Men’s cropped pants are cut a little bit above the ankle. This gives a clean look that adds a bit of edginess compared to your usual regular pants. Whether you want to show off your ankles or you want to make your outfit standout with a playful pair of socks, it is all up to you on how you style and rock your cropped pants. We’re here to help you out by giving all the ins and outs of how these pants should fit, how to style them, the different kinds of folds to style pant legs, important rules to follow, and what shoes to wear with them. But before anything else, its always good to take a look back and see where this style came from to better understand how to style them.

History of Cropped Pants

So, let’s cut to the chase – how did cropped pants even begin? Just like most fashion pieces, these pants have evolved throughout history and actually started out by being worn in a very different way. Cropped pants originated or at least were inspired by women’s capri pants. These capri pants started being worn shortly after World War II. The designer and genius behind these pants was Sonja de Lennart. Her first design started as cropped, close-fitted trousers.

Since de Lennart designed capri pants, they became very popular and the trend of wearing cropped bottoms rocked the world of fashion. It became so popular that shortly after, even men started opting for this look. Hence, that was when man’s capri pants started to be worn. This look has become popularized and made its way as a classic style staple in the fashion crowd.

How Should Cropped Pants Fit?

At first glance, anyone would assume that when it comes to cropped pants, it would be appropriate for beach trips and other outdoor activities. After all, who wants soggy or muddy pants? Cropped pants, however, are not just for beach trips. This versatile piece can be worn in different ways and occasions as long as the fit is perfect and your styling is on-point.

No one also wants to wear awkward oversized or overly tight pants. For a good fit, think of skinny or slim-cut jeans. They hug close to the body but leaving some space to move. Nothing too tight to the point of difficulty in breathing or too loose that it looks borrowed from someone else’s closet. Given the cropped style of the pants, the fit must be something in between skinny and baggy; just the perfect balance.

How to Style Cropped Pants

We all have to agree that one of the best parts of living in the 21st century is the openness and freedom to wear whatever we want as long as we feel comfortable. The fashion scene has been more accepting of new trends. But you also have to admit that there are simply some pieces that you need to style properly to pull off.

Cropped pants are one of the most versatile pieces out there. You can wear them almost anywhere! Different colors, patterns, and finishes are available in the market for cropped pants. As long as the cut and fit are perfect for your body, you can rock these bad boys in different ways. For those who’d rather go for more traditional and basic styles, you can go with navy, black, or white cropped pants. These are perfect choices, as these colors never go out of trend. For those who are a bit bolder and more dynamic, colors such as royal blue, burgundy, and emerald are perfect.

We know what you are thinking next… “Do cropped pants have a place for dressier occasions?” Well, yes! Men’s cropped dress pants with a suit look effortlessly chic. If you’re the type to look more laidback, then this look might be perfect for you. As long as the pants are not too short, then this look is fine for work or smart casual events. It is also best to stick with plain colored suits as well to avoid looking too flashy and casual.

This Is How We Roll

With cropped pants, you also have to learn the different ways to roll up your pant legs and give them a proper fold. These are the different kinds of folds that you can do and what styles it goes best with.

Loose Fold

Take a pair of your favorite trousers and simply fold or loosely roll the hem about two to three times. This should give a stylish height without being too contrived. The no-fuss tapered edges to the normal length pants work well with lightweight cropped chinos for men or denim.

Tight Roll

As its name implies, this type of roll leaves less slack around the opening of your pant legs. This is done by taking a bit of fabric from the hem then folding it in before you start rolling it up. This style is a lot more casual, which makes it ideal for jeans. It is great when you want to show off your pair of pristine white sneakers and rock the streetwear aesthetic. This fold will go very well with men’s skinny cropped pants.

The Once-Up

The Once-Up is a classic fold that gives your outfit a clean and sharp look. You can pull this off with almost any type of pants, but we highly recommend trying it out with a nice pair of dress pants. Before you know it, you’ll be using your work pants out for a party or even a leisurely stroll in the park or along the beach. You can try using an iron to make sure that the folds stay in place. If that doesn't work, consider using a safety pin hidden under the fabric to make sure it holds. This fold works naturally well in the summer but can also do wonders in the winter. It exposes just enough to still keep you warm while showing off a little skin.

Basic Rules for Pants

As much as we want to promote acceptance in all forms when it comes to fashion, we can’t help but discuss the different rules when it comes to wearing these ankle length pants for men. Here are just a couple of basic rules to always take note of when you decide to take out your pair of cropped pants and other options for you to wear your pants.

Cropped above the ankle, wear with no socks

When it comes to this look, good tailoring is a must. The pants must be very slim, especially towards the hem. This look can be pulled off with or without a cuff. Because the length of the short pants can make the person wearing them look shorter, this is best for those who are a bit taller than average with a slim physique. The footwear best for this would be brogues or loafers. Make sure that your shoes are well polished and maintained cleanly. Wearing cropped pants without socks will draw attention to your shoes. Finish off the look by pairing the pants with a well-tailored shirt, a light jacket, and a pocket square.

Cropped at the ankle with socks

This is a slightly more formal and less daring look. The hem is slightly longer, resting just above the foot with no break line at all. The pants are very tapered towards the bottom of the hem and can be either cuffed or uncuffed. The best socks for this look would be basic or classics that match the color of your tie or pocket square. If you are feeling more daring, socks with classic prints such as maroon diamonds are a great choice. Avoid going overboard or crazy with the colors since these would not really be that visible.

Half Break

This is probably the most recommended style for most people this year. This is perfect for slim or regular fit pants since the hem sits just over the rim of the dress shoes, and one bump of the hem fabric at the front. This is a modern but safe style which suits a lot of people, especially those who are a bit on the shorter side. This length covers the ankles fully and shows well-paired socks when sitting down. There are some men who choose not to have breaks, but still prefer the pants to cover their ankles. On these occasions, the trousers can be slanted to be slightly shorter at the front, thereby reducing the break.

Full Break

The full break is the classic length and is perfect for any man who prefers the more traditional look. It works perfectly with straight or wide-leg pants. The back of the pants comes right down to the end of the heel, and there are at least two bumps or breaks at the front. Hem tape is sometimes used to make sure the fabric won’t get damaged from rubbing on the shoes. This is a perfect look for dressier events that require tuxedos and work suits.

Not cropped

Just like a lot of things in life, cropped pants also come with exceptions. If you feel that your legs are very muscular, then cropped pants might not be the best choice as these tend to make you look a bit shorter than usual. Instead, go for pants that are at least a half break, and slightly tapered towards the hem. If the cut also is off or too awkwardly done, then this will ruin the whole look like the most important part of cropped pants would be the cut. The cut must be fully tapered towards the bottom of the hem. If the pants are a straight or wide cut and flaps around at the ankles, it will only make the man look as if he had accidentally outgrown the pants. Again, when it comes to almost all clothing pieces, fit is everything.

The 21st century is an open and accepting fashion world. If you have any hesitations about cropped pants because of your height, your muscular legs, or any other possible insecurities, then the best thing to do is to just make sure that your cropped pants fit you perfectly. They must be hitting at the right angle, which is around the ankle. If needed, get them tailored to fit perfectly. With the right top and shoes, the look can look seamless.

Some of the basic rules most men swear by when it comes to cropped pants would be to always balance out your outfit. Cropped pants tend to look best with a slimmer top. If the pants are already wide and you go for a wide top as well, you might end up looking too baggy. Neutral tones work best on almost any occasion. When in doubt, go for basics and avoid anything too loud. Footwear with a bit of heel looks good with cropped pants as these add a bit of height and make the look put together overall.  

What Shoes Do I Wear with Cropped Pants?

There are so many different things to consider when pairing your cropped pants with a certain pair of shoes. If you really think about it, with cropped pants, your shoes are really accented in your overall outfit. Eyes will go straight to the cropped area and take a look at what kicks you end up rocking that day. And as they say, “good shoes take you to good places”. This is especially true when it comes to dressing up well. Wearing the right shoes can make or break your look when paired with cropped pants.


This term may sound a bit strange but it simply means wearing shoes without wearing socks often look awkward or out of place in most situations. Not a lot of men are comfortable with this style since not a lot can pull it off. However, with cropped pants, this style works wonders. When you’re in cropped pants, showing off your ankles usually doesn’t cause a big fuss. This style works best for beach trips since it’s very convenient to just kick off your shoes and head straight to the waves. If you’re not heading to the beach and you think socks are a must, some opt to go for invisible socks or “sockettes.” These keep the dainty look that perfectly covers the feet while still leaving the ankles exposed.

Sneakers and cropped pants

Low-cut, white sneakers are a favorite partner for cropped pants. These are best worn with light cropped trousers or wool cotton trousers. Together with a collared shirt and some vintage sunglasses, this look is perfect for casual mornings. If ever you insist on wearing socks that would be visible, dark-colored socks without patterns are best worn with dark cropped pants. However, if you’re not the minimal type, bolder colors are also an option.

Espadrilles and cropped pants

For summer days, espadrilles and cropped trousers are a match made in heaven. For a smart-casual look, go for white or khaki cropped pants and a long-sleeved jersey shirt with the sleeves nonchalantly pushed back. Complete the look with some sunglasses and you are definitely good to go!

Dress boot and cropped pants

Colder days are inevitable and as much as you’d want to keep those ankles exposed, the frostbite might not be worth it. These boots sit nicely under rolled denim jeans or casual trousers. Dress boots that come in dark town or brown suede work well with raw denim jeans for an easy and casual day out.

Loafers / Oxfords and cropped pants

Cropped smart trousers have been an emerging trend in menswear during the past winter season. Its clean and natural fabrication makes it the perfect transitional trouser – day-to-night dressing has never been this easy. This is also perfect for weather changes as it adapts well to a lot of seasons.

Because of the cropped style of the pants, certain shoes do not really work well with them. An example would be boots or any footwear that are high-cut or tall enough to cover the ankles since this would defeat the whole purpose of the cropped pants. This minor limitation is not that big of a deal compared to all the other available footwear perfect for cropped pants.

According to a lot of gents out there, slip-ons or leather shoes are among the favorite footwear for cropped pants since these give the cropped pants a bit more character. Sneakers, such as laced canvas shoes, also work as long as the silhouette remains low cut. When it comes to footwear, it all depends on the occasion since these make an impact on the overall look.

Why You Need Cropped Pants

If you are still hesitant about cropped pants, just think that they are truly versatile pieces that you can wear almost anywhere with almost any kind of footwear and top. Whether you plan to go for a sunny day out at the beach or it is just another day at work, cropped pants can be your best friend. After all, they are not going anywhere and are just starting to be trendy once more, with new ways to style them showing up here and there. Cropped pants are light, breezy, but also perfectly put together, which make them perfect for an effortless good impression anywhere and across all seasons. If you are looking for a sign, now is the perfect time to put on those cropped pants and put yourself out there.

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