Fall is here and the time is right for ankle boots. What should you wear them with? Here’s how to wear ankle boots with any outfit and pull it off.

With fall weather comes pumpkins, red and orange leaves, mugs of hot apple cider, and our favorite, boots! Believe it or not, boots are actually a very versatile shoe option and can look great with nearly all your fall and winter outfits.

What boots go well with what outfit though? The answer is just about all of them. A nice pair of ankle boots can add a finishing touch to most outfits from a nice dress, to your favorite pair of skinny jeans and tights.

If you can wear an outfit with sneakers, you can probably wear it with booties too. Here are a few tips on how to wear ankle boots to create the cutest fall looks.

1. Tuck Them In

Tucking your pants into your ankle boots can make your legs look way longer than they actually are. You just have to make sure you get the right kind of pants.

Most pants don’t look right with this style. You’ll need to get a pair of leggings, jeggings, or skinny jeans. The ankle boots that make it easy to tuck are are high blocked heels and wedge heels.

High blocked heels look great with the jeans, and wedge heels are a good match for jeggings or leggings. It’s just a matter of what style of heel you want, and how tall you want to feel.

2. Rolled Hem

Rolled or even double cuffed jeans look really cute with booties and will allow for a little ankle to shine through. Showing that little bit of ankle will keep them from looking wide.

Enjoy this look with skinny jeans. Straight-legged and wide-legged pants will only shorten your leg line when they’re rolled. Again, the high block heel booties look great with these as will the low block heeled ones, and flats.

3. Cuffed

When wearing cuffed jeans, the key is the exposed ankle. You want your ankles to look as slim as possible and they can do that. You should try it with longer skinny jeans rather than pants that stop at the ankle.

The most flattering cuff is one that’s about 2-3 inches tall. As far as what style of booties you should wear with it, high blocked goes well with most jeans as does low blocked.

4. Half Cuff

A half cuff is a fun, effortless ankle booties outfit option that pairs well with an oversized t-shirt and sunglasses.

The point of this look is to look effortless so for the best effect you want to cuffs to not match. Keep them at the same height mind you, but roll them at slightly different angles and widths to make it look haphazard.

5. Layered Socks with Leggings

Despite how much we’ve told you that you want to make your ankles look skinny, you’ll need to bend the rules a little bit for this adorable Winter look. You do want to go for a fairly neutral colored sock though so as not to bring to much attention to your ankles. All you do is tuck your socks into your leggings and slap on your warm, comfortable ankle boots.

You want to wear the ankle boots over shorter socks rather than longer ones. They’re a lot less bulk that way. Never layer socks over jeans when pairing them with your booties unless it’s a very thin material like jeggings. Jeans will just make your ankles look fat.

6. Monochromatic

If you have trouble styling your taller ankle boots than this look is the answer for you.

Taller ankle boots cover up your entire ankle but a pair of black leggings and a black pencil skirt will create a long, sleek line that will make that irrelevant. Really bring this look home with a bright pattern top to contrast against the monochromatic bottom.

This doesn’t just work with black, you can do brown tights with brown boots, gray with gray, or mustard with light brown.

7. Wear Them With a Dress

Wearing booties with a dress is a choice that you might not gravitate towards at first when putting together your ankle booties outfit. It’s actually a pretty cute look if you wear a dress that stops above the knee.

The reason why you want it to stop further up is to give the illusion that your legs are longer. If you need a formal look that stilettos heeled ankle boots will work great.

Try wearing an all-black dress with these studded boots for example. Studs will actually add a touch of elegance to your outfit.

8. Socks and Bare Legs

Socks are really in lately, and they are a match made in heaven with ankle boots. Before we said you could wear them over your leggings, but the look actually works pretty well if you take out the leggings.

Again, make sure the socks are a neutral color. If your skin is light and your socks are dark it will give you some pretty strange proportions. Keep your dress above your knees to show off your legs and make them look longer.

Learn How to Wear Ankle Boots with All Your Favorite Outfits

Chances are, there aren’t many outfits in your closet that your ankle boots won’t pair nicely with. These are just 8 ways on how to wear ankle boots to get you through the beautiful Fall and Winter months It almost boots season!

To get more ideas for cute Fall looks, visit the fashion section of our blog.