The Ultimate Guide to Styling Men’s Ankle Boots: Trouser Pairings for a Fashionable Winter Look

Compared to tall boots, ankle boots are easier to style and have lower requirements for body shape. They can meet the diverse styling needs of men’s daily life in various occasions, allowing you to look dashing, gentle, and handsome at the same time.

Smart individuals have already gotten their hands on a pair of ankle boots for the winter, but boots can be a magical item that “eats up” your legs. They cover the slimmest part of your ankle, making it easy to appear as if you have shorter legs.

Today, we’ll discuss the best trouser partners for several common types of ankle boots, as well as the most suitable trouser length for creating the illusion of long legs. Even in the coldest months, we mustn’t be careless.

1: Chelsea Boots + Dress Pants

Compared to the cool and stylish mid-calf boots, Chelsea boots are more suitable for business casual occasions, paired with semi-formal menswear.

They’re also a good choice to replace traditional dress shoes during the year-end party season. The grip and warmth of Chelsea boots are incomparable to derby and Oxford shoes, making them stress-free even on snowy days.

When wearing Chelsea boots with elastic gussets, it’s best to choose dress pants with a simple and clean overall design.

If you want to stand out more, you can play with the leather texture of the boots, such as multi-layer hand-dyed, patent leather, or suede. A brogue toe design is also a good choice.

2: Hiking Boots + Jeans

The rough texture of cowhide creates a rugged feel, while the riveted metal parts at the lacing area strongly align with the popular workwear style. Additionally, the comfortable fit makes them one of the most favored styles in winter.

When it comes to outdoor activities, comfort and practicality are paramount. The best way to showcase this style is to retain its inherent beauty without the need for too much decoration. Jeans are undoubtedly the most suitable choice, easily paired with windbreakers, cotton coats, down jackets, and even parka coats, all while maintaining a sense of style.

3: Desert Boots/Derby Boots + Smart-Casual

The rough and warm texture of desert boots has always been the single most fashionable item in the city, while the intellectual and elegant character of derby boots makes them the easiest to possess a retro and refined style.

Derby boots, needless to say, in classic black and brown, can match almost all the pants in your wardrobe, except for sweatpants. Desert boots, a type of soft leather ankle boots, are very comfortable to wear and more suitable for men with wider feet compared to zippered ankle boots.

You may think they are most suitable for spring and summer, but in fact, winter is the best time to show off your skills. If you’re smart enough, wearing a turtleneck sweater and wool dress pants creates the most elegant office look. Desert boots are not picky; paired with the must-have khaki pants and Oxford cloth shirts for straight men, they are also a good combination for playing mahjong with parents during the Spring Festival.

4: Brogue Boots + Wear with Anything

Escaping from various trendy points and small details, a pair of classic brogue boots is undoubtedly a must-have in your winter shoe cabinet. Avoid delicate sheepskin and overly eye-catching patent leather; tough and elastic cowhide is the first choice.

Seven-hole or eight-hole brogue boots are an essential basic style among boot options. Not only are they fashionable and durable, but they also look better with wear and can easily handle various winter trouser styles. Whether it’s wool dress pants, jeans, corduroy pants, plaid pants, or striped pants, as long as they’re not wide-leg pants, brogue boots can handle them all.

Having discussed the best trouser partners for common ankle boots, let’s talk about trouser length.

Generally speaking, the safest method is to pair them with slim-fit trousers and tuck the trouser legs into the boot shaft, which looks neat and sharp without any sense of redundancy. If your legs are not long enough to pull off pants with a slimming effect, you might want to try folding the trouser legs. Depending on the height of the boots, adjust the width of the fold to be between 2-5cm, naturally covering a bit of the boot upper. This way, when walking or sitting, not too much skin or socks will be exposed.

▲ Ankle Boots with Suit Pants

When pairing ankle boots with suit pants, it’s best to choose casual styles and avoid being too formal. Tucking loose suit pants into boots, if not done well, can be suspected of being preppy. Regardless of whether the trouser legs are folded or not, they should just touch the top of the boot upper for a seamless connection.

▲ Good Partners for Ankle Boots

Don’t be surprised. As long as it’s not an overly strict office environment, a well-chosen, fitting pair of ribbed sweatpants can also become a good partner for your ankle boots. A good fit is still the premise. As for those wide and dragging styles, it’s best to stay away from them unless you want to be regarded as a hip-hop dude. In terms of length, it’s a personal preference whether to connect with the boot shaft or slightly cover the boots. Just avoid shiny patent leather boots.

▲Men’s Boot Styling Methods

Tucking pants into wool socks, with the socks exposed outside the boot shaft, is the most hardcore way to style men’s boots. However, if you have naturally short legs, please don’t try this. Bulky ankles will only make the already unfavorable proportions worse. What can be inadvertently exposed can be the skin on the legs or socks with a bit of thoughtfulness. To give people a refreshing feeling, socks are very important. The same color scheme as the clothes or eye-catching contrasting colors are both good. Those who pursue uniqueness can put more effort into the patterns.

Compared to the casual and lazy loafers and the energetic sneakers, a pair of handsome ankle boots can better highlight the unparalleled fashion sense of men this winter. Everyone, go and try them on!