How to Wear Ankle Boots with Dresses Pictures

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Ankle boots are commonly worn with leggings, jeans, or a really great skirt. But if you’re wondering how to wear ankle boots with dresses and need pictures to help visualize the outfits then keep on reading because this post has got you covered.

How to Wear Ankle Boots With Dresses- Pictures

Wearing ankle boots with dresses comes down to heel height and dress length. The best ankle boots with dresses are the ones that show off the boots while keeping the silhouette of your outfit balanced, shorter dresses for example paired with a heeled ankle boot adds length to the legs and is often preferred over flat ankle boots.

On the flip side of that a long maxi dress with flats can often feel a bit frumpy so a medium heel works really well, a midi dress looks great with both a heel and a flat. I personally love a midi dress with chelsea boots, the look has a western feel with added bonus of being comfortable.

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How to Wear Flat Ankle boots With Dresses

This style is a bit trickier since as stated above short boots with dresses can cut off height and make you feel a bit frumpy. A great rule of thumb is to wear a flat ankle boot that has even a tiny elevation to it so you don’t feel the ground when you’re walking, but you’ll enjoy the comfort that comes with a flat boot.

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How Do I Wear Ankle Boots

When determining how to wear ankle boots consider the following:

  • Colour
  • Ankle shaft height
  • Heel height
  • Toe shape
  • Dress length

Then consider what the occasion is for wearing the boots. Are you looking to achieve a business casual look for the office? Or need boots for everyday life? Whatever the occasion make sure to determine the goal of the outfit. Which could be to look put together and business casual appropriate for work, while maintaining a high level of comfort without compromising on style.

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What Kind of Dresses Go With Brown Ankle Boots

The great thing about brown ankle boots is their versatility. Brown and black ankle boots pair well with any colour dress and pattern. When thinking about dresses and boots remember they’re just like any other shoe, you just have to consider heel height and where the boot hits your ankle and calf.

Also consider pattern and colour of the dress, that’s why neutrals work so well as footwear and should be a part of your fall capsule wardrobe. If they already are that’s fantastic, if not and you need help determining what should be included in your fall capsule wardrobe I’ve got you covered. You can download a free work capsule wardrobe checklist here to use as a guide.

Boots also make a great staple for summer to fall transition outfits, the cooler weather makes boots practical and effective.

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Can You Wear Booties with a Dress to a Wedding

Absolutely! You will likely want to stick with a sandal in the summer but for fall winter and spring weddings a bootie would be a great option. Just make sure it’s not in a dark colour as that looks more casual, and might make finding a dress to pair with them difficult.

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ankle boots with dresses pictures


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3 Comments

  1. 9.17.22
    Cathy said:

    What do I wear with ankle boots when wearing the boots to a dress to a wedding

    • 9.21.22

      I would either wear a dress or a jumpsuit, depending on your personal style. Even a great pair of wide leg dress pants and a beautiful blouse would work.

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