Finding the most flattering ankle boots that are also in line with the latest trends may seem like a daunting task, but with a few pro tips, it’s actually easier than you think. Discover how you can rock ankle boots, whether you prefer stilettos or chunky heels.

Learn how to wear ankle boots to complete your style in a flattering way. From the latest trends to the best ways to pair them with skirts, dresses, pants and leggings, here’s what you need to know about ankle boots this fall.

Choosing Your Trendy Ankle Boots

A classic option that can be flattering for most body types, ankle boots come in all shapes and sizes, but you should always pay attention to the latest trends. For Fall-Winter 2014/2015, chunky block heels, lace ups and animal prints are among the biggest trends. 

Don’t be afraid to go for embellished ankle boots that seem a bit over the top, since this season’s trends are all about being daring.

Ankle Boots Outfit
photo: Ruby_1203

Picking Flattering Ankle Boots

The most important thing to consider when you’re wondering how to wear ankle boots is the proportion of the footwear in relation to your ankles and legs. While chunky heels are really trendy, they won’t work well if you have very slim legs. Likewise, ankle boots with super slim stiletto heels are not a good choice when your legs are fuller.

Ankle Boots Casual Outfit
photo: Hannah A

Ankle Boots for Hourglass Body Shapes

If you’ve got curves and a well defined waistline, you can jump straight to the hottest trend of the season: chunky heels. Avoid embellishments and cuff details if you have thicker calves, since they’ll add extra volume. Going for a monochromatic look, with pants or leggings in the same color as your ankle boots helps create a flattering look.

Ankle Boots With Shorts And Coat
photo: Nina

Ankle Boots for Inverted Triangle and Apple Body Shapes

If you’re top heavy or have an apple body shape, you can go wild with animal prints or attention grabbing embellishments. The right answer to the question of how to wear ankle boots is with a touch of flair. So don’t be afraid of bold colors and big embellishments, whether you prefer chunky heels or stilettos.

Ankle Boots Party Outfit
photo: Catia Sousa

Ankle Boots for Pear Body Shapes

Go simple if you’re bottom heavy and try wedges or chunky heels when you’re looking for the perfect ankle boot. Avoid big hardware and go for visible vertical zips for a more flattering effect.

Ankle Boots Outfit With Leather Jacket
photo: Mariana CastroMoreira

See also: Best Pants for Your Body Type

Ankle Boots for Rectangle Body Shapes

When you’re wondering how to wear ankle boots for a rectangle body shape, go for detailing. Stilettos can help create a flattering effect, but chunky heels also work, as long as the ankle boots draw the eye downward.

Ankle Boots With Jeans
photo: Amy Bell

Ankle Boots for Petite Women

Whatever type of ankle boot you choose, tucking your pants in them is a must if you want to extend your legs. Go for higher heels and as monochromatic look for the most lengthening effect, and opt for pointy toes.

Ankle Boots With Mini Skirt
photo: Christy Jaldori

Wearing Ankle Boots with Skirts and Dresses

Even though midi skirts are a big fall trends, they don’t necessarily go well with ankle boots. Keeping the proportions right is important, so if you want a longer skirt, you have to pair it with shorter ankle boots. For knee-high skirts and dresses, avoid taller ankle boots, since they’ll just make your legs seem shorter.

Ankle Boots With A Line Skirt
photo: Konstantina Tzagaraki

A-line skirts and dresses work best with ankle boots, but if you’re wondering how to wear ankle boots with a pencil skirt or tight dress, opt for delicate boots with stilettos heels.

Wearing Ankle Boots With Leather Leggings
photo: Silvia P

Wearing Ankle Boots with Pants

If you want your legs to look longer, tucking in your skinny jeans is a must. However, you can also roll or double cuff your jeans for a cool effect. Just make sure that you’re picking the right pair of skinny jeans and not straight-legged denim. Exposing your ankle with a cuffed hem will slim it down and make for a more flattering look. You can also try asymmetrical half cuffs for a more casual look.

Ankle Boots With Leggings
photo: Britnie Harlow

More: 10 Most Common Fall Fashion Mistakes

Wearing Ankle Boots with Leggings

The monochromatic look is the perfect answer to the question of how to wear ankle boots with leggings, and black is slimming and works for every body type. Leggings should always be tucked in your ankle boots, and if you’re going for a monochromatic look on the bottom, be sure to compensate with a brightly colored top.