How To Wear Ankle Boots and Booties With a Dress: 10 Chic Ways

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Wearing dresses with boots has been a trend since the 1970s when over-the-knee boots and mini skirts were all the rage. While boots now come in every shape and size, ankle boots are a go-to style for pairing with skirts of every kind.

This look can be adapted to be made appropriate for wearing all year round. While ankle boots are most often paired with denim jeans, we think a dress is the most versatile way of wearing your favorite booties.

Dresses with ankle boots are a celebrity-approved style that’s been seen on the likes of Taylor Swift, Kendall Jenner, and Hilary Duff.

To give you some inspiration for how to style ankle booties with dresses, we’ve put together a list of our top ten styling tips.

1. Contrast Your Dress and Ankle Boots

Take a leaf out of the ‘70s fashion bible and contrast your dress with your booties.

Pick up a pair of ankle boots in a fun color like white that can be easily styled with different dresses. A pastel dress will make the white boots pop even more.

Stacey Solomon, Sophie Hermann, and Kendall Jenner wear mini dresses with white bootsStacey Solomon, Sophie Hermann, and Kendall Jenner wear mini dresses with white boots

If you want to let your boots do the talking, choose a dress in a classic color and timeless silhouette. You can put a modern twist on a little black dress by adding a pair of baby blue ankle boots.

Gwyneth Paltrow, Kelly Brook, and Christie Brinkley team LBDs with contrasting ankle bootsGwyneth Paltrow, Kelly Brook, and Christie Brinkley team LBDs with contrasting ankle boots

2. Pointed Black Ankle Boots Match Every Dress

If you want to invest in only one pair of boots, it has to be a pair of pointy black ankle boots.

These boots are the supporting act to your outfit, allowing your dress to take center stage if you chose a solid jewel tone color or animal print.

Chloe Paige, Sophie Porley, and Paris Hilton in animal-print dresses with pointed-toe ankle bootsChloe Paige, Sophie Porley, and Paris Hilton in animal-print dresses with pointed-toe ankle boots

If you are looking for a more minimalistic outfit, then nothing beats a pair of black ankle boots. These shoes can be paired with midi-dresses for formal events or mini dresses for a girl’s night out.

Throwing on a black dress with black tights, cute booties, a great coat and throw a scarf over it. I think simple accessories and, if you want to make a pop, a great red lip – Meghan Markle

This style of shoes is a staple in the closet of legendary Vogue Editor in Chief Anna Wintour, who is one of the biggest advocates for wearing ankle boots with a dress.

Alexa Chung, Karen Gillan, and Nicole Scherzinger wear dresses with black pointy ankle bootsAlexa Chung, Karen Gillan, and Nicole Scherzinger wear dresses with black pointy ankle boots

3. Chunky Boots Add An Edge To Any Dress

With this style of ankle boots, you can take a simple white pleated dress and make it street-style ready.

Chunky ankle boots with rubber platform soles or lace-up military-inspired ankle boots are a great seasonal addition to your closet and are perfect for colder months.

These boots have a big personality and should be paired with more minimalistic dresses to balance out your look.

Taylor Swift, Gabby Allen, and Fearne Cotton wear minimalist mini dresses with chunky ankle bootsTaylor Swift, Gabby Allen, and Fearne Cotton wear minimalist mini dresses with chunky ankle boots

4. Maxi Dress & Ankle Boots = The Dream Team

This duo is the ultimate autumnal chic look and is a favorite of celebrities like Rosie Huntington-Whiteley and Katie Holmes. Ankle booties can make any of your favorite summer maxi-dresses more wearable for autumn and winter.

The key to carrying off this look is to choose ankle boots in monochrome or earth tone colors.

Ankle boots with a high heel achieve a sophisticated vibe, whereas flat ankle boots can help dress down this look to make it everyday appropriate.

Myleene Klass, Emma Roberts, and Kristin Cavallari in maxi dresses and ankle bootsMyleene Klass, Emma Roberts, and Kristin Cavallari in maxi dresses and ankle boots

5. Embrace The Western Look

For the bohemian fashionista, cowboy ankle boots can help create a laid-back retro-inspired look. For a fashion-forward look, choose a dress in an electric color like yellow or purple, and add a matching belt to fully embrace the modern western aesthetic.

This style of ankle boot tends to feature a low and wide heel, making them ideal for wearing for hours on end while you’re running around town.

If you want to stay true to the heritage of these boots and embrace your inner cowboy, chose a pair of western-inspired ankle boots in a tan brown or distressed black.

Rachel Stevens, Karina Smirnoff, and Katharine McPhee go western in printed dresses and western bootsRachel Stevens, Karina Smirnoff, and Katharine McPhee go western in printed dresses and western boots

6. Nude Boots Make You Appear Taller

One of the greatest fashion myths is that short people can’t wear ankle boots. The opposite is true.

Nude boots are the perfect way to elongate your legs and give the illusion that your body is leaner and taller as it creates the perception of a longer line.

Blake Lively, Kendall Jenner, and Ashley Tisdale pair their tiny dresses with leg-lengthening nude ankle bootsBlake Lively, Kendall Jenner, and Ashley Tisdale pair their tiny dresses with leg-lengthening nude ankle boots

7. Midi Dresses & Ankle Boots All Year Round

Ankle boots and midi-dresses are a perfect transitional outfit that can be worn all year round, and easily adapted for the season.

Choose light-weight dresses with cap sleeves for spring and summer, and then chose knitted dresses and heavier fabrics for autumn and winter.

You can make this look work even during the coldest of days by layering up with thick tights and your favorite coat to bundle up in.

Midi dresses allow for a flash of skin, and you can even show off a quirky pair of socks or an embossed pair of tights.

Agyness Deyn, Elle Macpherson, and Ever Carradine wear midi dresses with ankle bootsAgyness Deyn, Elle Macpherson, and Ever Carradine wear midi dresses with ankle boots

8. Combat Ankle Boots Can Completely Change a Look

If your style is more rock chic then combat ankle boots are your new best friend. These shoes instantly add a masculine twist to even the most floral of dresses.

The combat booties are a go-to style for celebrities such as Hailey Baldwin, who juxtaposes rose-printed dresses with oversized men’s jackets and black leather combat boots. This style is ideal for the woman who mixes both men’s and woman’s fashion.

Olivia Palermo, Kaia Gerber, and Irina Shayk toughen up their feminine dresses with black combat bootsOlivia Palermo, Kaia Gerber, and Irina Shayk toughen up their feminine dresses with black combat boots

9. Tall Ankle Boots Are A Must-Have

If you plan on pairing your ankle boots with dresses, then be on the lookout for booties with a taller shaft.

This not only helps to elongate your legs, but they are the most versatile type of ankle boots to wear with different lengths of dresses.

They can be styled with everything from a mini-dress for a night at the club or with a maxi-dress for a winter day out.

Adriana Lima, Nesta Cooper, and Christie Brinkley team their dresses with tall ankle bootsAdriana Lima, Nesta Cooper, and Christie Brinkley team their dresses with tall ankle boots

10. Wide Ankle Boots Create a Slimming Look

Dresses, in general, are the perfect garment to accentuate your natural silhouette and to help you to appear slimmer. In the same way, wide ankle boots can give the illusion of your calves being slimmer, which also creates the appearance of longer legs.

These two items are a perfect combination together and will give you the confidence you need to tackle whatever the day brings.

Their versatility means that ankle boots can be worn with any style of dress, and they can fit seamlessly into any woman’s wardrobe.

Michelle Williams, Jessica Alba, and Roxy Horner wear dresses with wide ankle bootsMichelle Williams, Jessica Alba, and Roxy Horner wear dresses with wide ankle boots

I always feel the most comfortable in a breezy short summer dress and a pair of ankle boots – Keltie Knight

Credit: Lia Toby / Avalon / Mario Mitsis / Lia Toby / Steve Searle / Rocky / 
VALPO NNEWs / Tical / JFXimages / Michael Wright / Adriana M. Barraza / 
Ivan Nikolov / Instar / WENN

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