20 Stylish Winter Looks With Ankle Boots

Tall brunette wearing a dress with a sweater tied around her waist, a hat, and black ankle booties with socks
This adorable look is perfect for the girly girl (photo: whowhatwear.com)

Ankle boots aka booties are an absolute savior when it comes to winter temperatures. They look chic, they keep your feet warm, and they’re insanely comfortable! The best part about them is that unlike taller boots which can overwhelm short women, ankle boots look fabulous on everyone. They come in so many fun styles that you can choose from including flats, heels, wedges, cut-outs, and in so many different materials. And let’s face it, what woman doesn’t love variety?

How to wear booties stylishly

Let’s now talk about a few dos and don’ts when it comes to ankle boots.

  • Do tuck in skinny jeans into your booties but don’t do the same with looser fitting pants because you could end up looking stumpy. You can roll your looser pants such that they end about half an inch over your boots.
  • Gladly wear them with pencil skirts and midis but avoid them with very short skirts.
  • They’re also great for maxi dresses and skirts as long as you show some leg.
  • They can also work with office pants when worn right.
  • Lastly, don’t be afraid to rock ankle boots like there’s no tomorrow.

Here are a few winter outfits with ankle boots to inspire you.

1) Rolled up Jeans

Roll up your denims such that they end right above your booties.Photo: lifestuffs.com

High waisted jeans hide “problem areas” and look adorable on everyone. Rolled up or “cuffed” jeans looks so amazing if worn properly! Channel the 90s by pairing your blue denims with a black coat and sexy black ankle boots. Break the monotony with a printed tote and voila!

2) Straight Jeans

Woman in straight jeans and ankle boots (photo: chicisimo.com)Photo: chicisimo.com

You can’t go wrong with ankle length jeans and ankle boots. They’re the perfect length to show off your boots without having to worry about whether to tuck it in or roll them up.

3) A pop of color

Here is one way to make sure you never look boring.Photo: thefashiontag.com

This one is for all the girls who believe that fashion should be about having fun with your look. If you must go for a neutral outfit, don’t be afraid to pick shoes that will make heads turn.

4) Perfect for Work

Ankle boots are great for work and play.Photo: glaminspire.com

If you think ankle boots can’t be worn with formal clothes, think again. Black ankle boots are a great replacement for you regular work ballet flats. Wear them with cropped khaki pants, a white top, and a gray coat and get ready to dazzle at work.

5) Skirt it up

Skirts with leggings go great with ankle boots.Photo: fustany.com

Just because it’s winter, doesn’t mean you can’t throw on a skirt. This is exactly what tights were invented for! We love the contrast of the white top and skirt against the black leggings and booties. The entire look is very feminine and ultra-chic.

6) It’s all about the layers

You just can't go wrong with layers.Photo: theverygirl.com

While it’s more common to see dark ankle boots, especially during winter, white ankle boots are just as fabulous if not more. Wear yours with some smart layers and you’re ready for a casual winter brunch with the girls.

7) Have fun with it

This adorable look is perfect for the girly girl.Photo: whowhatwear.com

If winter is mild where you are, you can simply take a summer dress and make it winter-worthy by throwing on a cute jacket and black ankle length boots with white socks. Add a playful touch to the look by tying a sweater around your waist and throwing on a hat. Hats are always fun!

8) Matchy Matchy

This style is fabulous when done right.Photo: freshdesignpedia.com

While current trends advise against matching your coat and bag to your shoes, rules are always fun to break. Even more so, when they involve a beautiful bright color like this one. Our only word of advice: keep the rest of your outfit as simple as possible.

9) Silver Fox

Make a statement with silver ankle boots.Photo: wheretoget.it

Sometimes it’s all about making the right statement and these boots do just that. They scream quirky and fun. We love that the rest of the look is relatively somber, allowing the shoes to get all the attention they deserve!

10) Fabulous Office Look

This office look is both comfortable and stylish.Photo: theeverygirl.com

Patent leather booties work great as office wear. They have an air of sophistication and are extremely versatile and wearable. Pair your patent boots with gray ankle length trousers and a gray sweater. A white pea coat will keep you warm and add some extra flair to the look.

11) Simple and Sexy

A camel coat complements black ankle boots beautifully.Photo: us.shein.com

Sometimes, it’s all about classic pairings that work together unfailingly. Keep it simple with a camel coat, sheer leggings, and black ankle boots.

12) Keep it Short

Now this is a cute winter outfit!Photo: freshdesignpedia.com

Who says you can’t wear shorts when it’s cold outside? Just layer it with some fleece lined leggings and throw on some block heeled ankle boots and last but not least, don’t forget the chunky scarf.

13) Printed Pants

Boho chic girls will love this look!Photo: seconds96.rssing.com

If you’re bored of regular jeans, throw on a pair of skinny military pants with your ankle boots. Add a feminine touch with a fluffy coat. It’s unusual yet chic and will really bring out your inner fashionista! Can you say wow!

14) Get down and funky

A funky look that will make you the center of attention.Photo: pinterest.com

As they say, monotony is the mother of all deadly sins. So, break the monotony and dare to be different with a look like this. Throw on a statement top with boyfriend jeans and flat ankle boots. Don’t forget a sweet little pink coat. Comfortable and fun!

15) Animal Print

Get adventurous with a pair of python ankle boots.Photo: pinterest.com

Everybody needs to take pointers from this cool cat’s (or should we say python’s) ensemble. On one hand, it’s a regular outfit with the white turtleneck sweater and boyfriend jeans but she absolutely takes it to the next level by throwing on a suede coat and python ankle boots. Love!

16) Haute Couture

Woman wearing a statement coat faux fur and patent ankle boots.Photo: frenchstyle.com

The fact of the matter is that not everyone can pull off this exaggerated haute couture look but where’s the fun in being “safe”? We love this look for a dreary winter day!

17) Rocker Chic

This modern rocker chic look is such a cool option for winter.Photo: fashiongum.com

There’s just something effortlessly chic about this look that we love so much! It’s simple, well put together, and so edgy!

18) Wedge Boots

Wedge ankle boots add just the right amount of drama to your look.Photo: fashiongum.com

Wedge shoes are a blessing for girls who have a love-hate relationship with heels. The draped gray coat adds a lovely contrast to the geometry of the wedge ankle boots. All in all, this is a gorgeous winter look.

19) Metallic is the way to go

Draw all the attention to your feet with this look.Photo: whowhatwear.com

The metallic trend can go very wrong, very quickly, if you go overboard but of course, Alexa styled her metallic ankle boots perfectly by keeping her ensemble simple and chic.

20) Classic looks never fail

This is a great go-to look for every woman!Photo: fashiongum.com

Now here’s a look that literally any woman can pull off. We love that this look can be dressed up or down depending on where you’re going and we love the pointy toed boots. So sassy!