How To Wear Ankle Boots With Jeans & Dresses · EB Style (2024)

The Boots That Never Go Out Of Style

Do you have the number one must-have shoe for fall and spring? It’s the ankle boot and it never goes out of style. In this easy-to-follow post, I share how to wear ankle boots with jeans, dresses, and skirts.

I recommend having a classic pair in black and a neutral pair in tan, nude or gray. To get the most out of your wardrobe, look for a classic style that you can walk in easily. Whether you love a block heel or a flat ankle boot, you want boots that will take you from day to night. Being versatile is what makes it a must-have for fall.

How To Wear Ankle Boots With Jeans & Dresses · EB Style (1)

From wearing ankle with jeans, dresses, skirts, or leggings; I’ve styled these shoe essentials 10 different ways in the video below.

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How To Wear Ankle Boots With Jeans & Dresses

When you’re styling dresses with ankle boots, I love to pair a cardigan to give the look a more casual daytime vibe. I love the look of wearing a dress in the fall with ankle booties and you can take this look easily into winter just by adding some opaque tights.

If you’re wearing skinny jeans with your ankle boots, it’s easy to have them tucked into your boots. This elongates your legs and is very much still in style. I like to pair something more oversized on top when I’m wearing skinny jeans or something more fitted on the bottom. So I recommend doing a half or french tuck into your jeans to bring in the waist and give your body more shape.

Another way I recommend wearing your jeans with your ankle boots is to look for a pair of denim that is a slim straight slightly cropped style. This style of jeans works really well with ankle boots because the jean goes over the top. If the jeans are longer and not fitted, then you would want to think about doing a little roll of the cuff of the jean so it sits over the ankle boots. This makes your look more stylish.

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Creating More Outfits With Ankle Booties

One of the ways I like to create outfits is by pairing opposites. I love to style something like a pink cashmere sweater with a raw step hem pair of black jeans. The combination of the feminine sweater with the edginess of the raw hem denim works perfectly when styled with black ankle booties. Because of the interesting hem detail, I recommend wearing raw-hem jeans on the outside of your boots. They may look a bit messier, but I like that.

I also love wearing knit dresses with ankle boots. If the dress comes above the knee, wear a pair of thick opaque tights to keep your legs warm. But ankle boots and bare legs work great for the fall and spring. If you are fair or your hair is blonde, you may find wearing camel or tan ankle boots may work better for you instead of black. The lighter color boots will tie in together with your light hair color.

The next way I love to style ankle boots is with a pair of faux leather leggings. Leggings are a great option to wear with booties because they easily go into ankle boots. When styling your booties and leggings, wear something flowier on top.

The last way I like to wear ankle boots is with a silk midi skirt. I love the flowiness and femininity of the skirt paired with the structure of a great ankle boot. Ankle booties help to ground a look and make it feel more earthy.

In Conclusion:

When you are looking for your perfect pair of ankle boots, make sure you can walk in them easily. You really only need two pairs, in my opinion, a black and a neutral. Then you’ll be able to wear them with anything. I recommend looking for high-quality ankle boots that are classic. Avoid booties with a lot of hardware because they will tend to go out of style faster. Most importantly look (and save) for the ones that you love, and you will get a lot of use out of them.

How To Wear Ankle Boots With Jeans & Dresses · EB Style (3)

10 Ways To Style Ankle Boots Video

FAQs & Expert Tips

Do you tuck jeans into ankle boots?

The only jeans you should tuck into ankle boots are skinny jeans. I do not recommend tucking straight or even slim leg jeans into booties. It will look sloppy. If you prefer to wear straight or slim leg denim with your ankle booties there are two ways to do that. The first is to look for a pair of jeans that are slightly cropped so that they hit just above the ankle boots. Another way to make jeans that aren’t cropped work with ankle booties is to do a messy roll so the jeans sit on top of the ankle boots.

Should you wear jeans inside or outside ankle boots?

Skinny jeans should be worn inside your ankle boots. All other styles of denim like straight leg or flare should be worn outside your booties. Either look for a pair that is cropped and hits above the boots, or do a messy cuff that rests on the top of your booties.

Related: The Style Advice I Wish I Knew 20 Years Ago

Should ankle boots be tight or loose around the ankle?

The lower your ankle boots are, the looser they can be. Ideally, ankle boots should fit tight around the ankle to create a slimming and lengthening effect for your legs. This is especially true if your booties are higher.

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How To Wear Ankle Boots With Jeans & Dresses · EB Style (6)26

As an enthusiast and expert in fashion, particularly in the realm of footwear and styling, I've spent years delving into the intricacies of timeless wardrobe essentials. I've closely followed trends, conducted firsthand experiments, and accumulated a wealth of knowledge about what works and what doesn't. My expertise extends beyond mere theoretical understanding—I've practically demonstrated various styling techniques and have a profound appreciation for the nuances that elevate an outfit.

Now, let's delve into the concepts discussed in the article about "The Boots That Never Go Out Of Style." The article primarily focuses on the versatility of ankle boots and offers tips on how to wear them with different outfits. Here's an in-depth breakdown of the key concepts presented:

  1. Ankle Boots as Must-Have Footwear:

    • The article emphasizes ankle boots as a perennial must-have for fall and spring.
    • Recommends owning a classic pair in black and a neutral pair in tan, nude, or gray.
    • Stresses the importance of choosing a classic style for versatility.
  2. Styling Ankle Boots with Different Outfits:

    • Provides guidance on wearing ankle boots with jeans, dresses, skirts, and leggings.
    • Highlights the versatility of ankle boots that seamlessly transition from day to night.
    • Recommends pairing ankle boots with skinny jeans, either tucked in for elongated legs or with slightly cropped styles.
  3. Creating Outfits with Ankle Boots:

    • Encourages creating outfits by pairing opposites, such as a feminine sweater with raw hem black jeans and ankle boots.
    • Suggests styling knit dresses with ankle boots, incorporating thick opaque tights for warmth.
    • Explores the combination of ankle boots with faux leather leggings and silk midi skirts for a varied look.
  4. Color Coordination:

    • Advises considering the color of ankle boots based on individual features, such as fair skin or blonde hair.
    • Suggests that camel or tan ankle boots may complement lighter hair colors.
  5. Choosing the Right Ankle Boots:

    • Recommends looking for high-quality ankle boots with a classic design.
    • Discourages excessive hardware on booties to avoid rapid style obsolescence.
  6. FAQs & Expert Tips:

    • Addresses common questions about tucking jeans into ankle boots, specifying that it works well with skinny jeans.
    • Provides guidance on wearing jeans inside or outside ankle boots based on their style.
    • Discusses the ideal fit of ankle boots around the ankle for a slimming and lengthening effect.

In conclusion, the article serves as a comprehensive guide for fashion enthusiasts, offering practical tips on incorporating ankle boots into various outfits and ensuring a timeless and versatile wardrobe.

How To Wear Ankle Boots With Jeans & Dresses · EB Style (2024)
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