Learn how to wear ankle boots with pants to make a trendy fashion statement

Learn how to wear ankle boots with pants to make a trendy fashion statement

A boot that extends to the ankle and no further is an ankle boot. They come in all shapes, styles, colors, materials and can be very casual looking or elegant. It can be tricky to style this style of footwear successfully, unless you are clear on how to wear ankle boots with pants, skirts and dresses of varying lengths.

This footwear is sometimes referred to as a bootiesIdeally, it is worn with skinny jeans or slim-fitting pants. When wearing them with skinny jeans, you may find a pointy-toe shape with a tight fit around the ankles is the best look for you. Try various versions and see which is more flattering before buying a pair. 

Avoid the Balloon Effect

If worn with boot-cut jeans, flared or wide-leg pants, the bottom of the pant is going to bump into the top of the footwear, creating a bunched up effect, particularly if the wearer tries to tuck her pant leg into the boot. Do not attempt tucking the pants into the shorter boot unless the pants are very tight or straight-legged. You want to avoid the ‘balloon effect’ at all costs.

You can wear them with leggings/jeggings if you look good in this type of apparel. If you don’t, and you know who you are, the footwear isn’t going to help. 

Some fashionistas recommend wearing this type footwear with light colored/skinny jeans. They believe the shorter version footwear is much more flattering to the wearer than knee high boots coupled with light jeans because the latter tends to shorten leg length while the shorter shoe elongates the leg.


This style of footwear goes well with printed skinny jeans. A taller boot tends to divert attention away from the printed pants or the combination of the print and tall footwear is too busy whereas shorter footwear allows the focus to be on the pants. 

Starting Out

If you are new to this look, start out with a dark color. Consider a cowboy style, featuring a pointy toe. If you are going for the urban look, choose a lower heel. 


For those of you who are hipsters, a flat, slumpy round-toe version is a good choice. Out on the town on Saturday night? Put on white, black, gold or silver high-heeled low-cut boots, pairing them with skinny pants or a skirt or dress. You can’t miss with this look.

Other options include wedge or stacked heels, which give you some additional height but don’t require the balance of a ballerina that stilettos do. 

Keep in mind, this type footwear can be flat, or possess a low heel or a very high heel, which makes it a good choice when selecting shoes. Ankle high moccasins are one version of this look as are low-rise cowboy boots. If you like the rock star look, wear a studded, blinged up pair, the higher the heel, the better.

If the boots and skinny/tight pants are worn in the same color — for example, brown footwear with brown pants — this is slimming and lengthening. There is no line of demarcation between the pants and the footwear because they are the same hue. This helps maintain the leg line and makes the leg look long and unbroken. 

Not Bulky

One of the best perks of this type footwear is you get extra height (if it has a heel), coverage, warmth and protection in the winter, but you do not have to deal with the inherent bulkiness of the taller version.

Essentially, this is going to be one of the, if not THE, most multipurpose pair of shoes you have ever purchased. You can wear them year around and wear them casually or when you are dolled up to the max. 


Avoid buying wide-topped footwear because the excess width cuts the wearer off at the ankle.