This Is How You Should Wear Ankle Boots With Dresses

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The next time you're about to style your dress with sneakers, stop. The look was cool and easy for Summer, but come Winter, we're challenging you (and ourselves) to wear a dress with ankle boots. This outfit combo seems easy in theory, but putting together a look is actually a little hard. In my case, I always feel like ankle boots cut off my legs when I'm in a dress, which makes me look shorter.

Though I've since discovered that a heeled boot is my best friend, I have a feeling other fashion girls out there struggle with similar problems. To help us all out, I found 10 different ways to wear the two items together thanks to some street style inspo. I included a few shopping picks, too, just in case you can't wait to test out the looks.

Getty | Daniel Zuchnik

To make your outfit stand out, don't go for that simple pair of boots. This street style star took a chance with her multicolored and embellished shoes, which happened to perfectly match the floral details on her sheer dress. And that sequined jacket? It added a nice, glittery touch.

Getty | Christian Vierig

If your dress has an interesting print or cut, go for ankle boots with a similar texture or feel. Nadia Ali nailed the look in her black MSGM dress and Lala Berlin boots.

Getty | Vanni Bassetti

Hanneli Mustaparta kept her look glossy from head to toe. Find a color in your dress that you'd like to match to your shoes. Bonus points to this street style star for styling her boots with a pair of black socks that matched back to her dress.

Getty | Christian Vierig

One way to pull off the matchy-matchy look if your dress is not the same color as your shoes is with accessories. Saheedat's cream-colored belt coordinated with her chunky ankle boots for a fun, festival-ready outfit.

Getty | Edward Berthelot

If you're wearing a colorful dress, consider wearing an equally as colorful boot. The pink and green hues in this outfit work because they're in the same color family aka pastels. This street style star is giving us the ultimate mermaid vibes.

Getty | Christian Vierig

An ankle boot plus dress is simple enough, so take it next level with a pair of jeans. This layering hack as done by Gine Margrethe is what separates fashion girls from the rest of the pack.

Getty | Christian Vierig

If your dress is a feminine style, go the complete opposite with your footwear. Aimee Song wore a pair of edgy, buckled ankle boots with her ruffled pink minidress for that cool-girl feel.

Getty | Edward Berthelot

When you want to let the print or color of your dress shine, just wear a pair of black ankle boots. It won't distract from your look.

Getty | Christian Vierig

We love wearing body-con dresses with heeled ankle boots, as it makes us look a little taller too. This model took a fashion-girl tip and matched her blue boots to one part of her dress.

H&M Chiffon Dress
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H&M Chiffon Dress

We're imaging all the ways we can style H&M's ruffled dress ($40), starting with a pair of black buckle boots.

Maggie Marilyn Shirt Dress
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Maggie Marilyn Shirt Dress

The color and asymmetrical cut on this Maggie Marilyn shift dress ($625) allow you to wear it with any ankle boot style.

Zara Long Shirt Dress
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Zara Long Shirt Dress

We would probably wear a red boot with this Zara shirtdress ($70) just to give it a fresh new take.

ASOS Ankle Boots
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ASOS Ankle Boots

This ASOS red boot ($72) is right on trend for Fall.

Tibi Sock Boot
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Tibi Sock Boot

Tibi's white sock boot ($595) will be one of your go-to shoes for Fall.

Isabel Marant Ankle Boots
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Isabel Marant Ankle Boots

When your dress needs a little zing, slip on this pair of Isabel Marant ankle boots ($885).

Madewell The Pauline Boot
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Madewell The Pauline Boot

This classic Madewell boot ($228) will never go out of style.