What Dresses to Wear with Over the Knee Boots

by Kathleen Loxton
What Dresses to Wear with Over the Knee Boots - tan over the knee boots with long white lace dress

A wise woman once said, “Give a girl the right pair of shoes, and she can conquer the world”; and, in terms of shoes, a great pair of boots is a necessary addition to any wardrobe arsenal. Over the knee boots have one of the toughest reputations amongst footwear to get right, so we’ve put together a list of what dresses to wear with over the knee boots. Consider these your next mission…

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Dresses to Wear with Over the Knee Boots

Day Dresses

Jessica Hart in white high neck dress with over the knee dark grey bootsGwen Stefani wearing blue check dress with black over the knee boots and tights
Photo Credit: Pinterest

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You may be hesitant to purchase over the knee boots for everyday use as they can seem trickier to pair with the right outfit compared to other styles. But they can go with lots of different items in your closet – you just have to know how to use them. For day dresses to wear with over the knee boots go for a style that can be versatile when being matched to shoes; structured and basic shapes will keep your look polished, while more relaxed styles suit more causal boots. For example, maxi style dresses are ideal if you’re questioning what to wear with tan boots.

An over the knee style for everyday use should be easy to walk in – think flat or with a sturdy heel – and boast classic colours and details. You can then pair them with accessories or various colours of dress to complete your look.

Evening Dresses

Gigi Hadid in gold long sleeved dress with light brown over the knee bootsRosie Huntington in black dress with v-neck paired with over the knee boots
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Cara Delevingne in kimono with black over the knee boots

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An evening out on the town doesn’t mean you have to leave your over the knee boots at home! The way to make them suitable for evening attire is to pick the right dress to wear them with. Cocktail length dresses are a perfect solution when working out what to wear with over the knee boots on a special occasion; you just need to be conscious of the rule of balance. If the dress is long sleeved and high necked, your hem can be shorter to show off your shoes; but if it’s low cut, make sure the hem is longer or go for well-chosen cut-outs like Cara Delevingne.

To make your over the knee boots more formal, consider the heel. Generally, the more stiletto-like it is, the more formal it’ll be. When it comes to fabric choice, smart suede or leather will work wonders.

Work Dresses

Olivia Palermo Long sleeved blue check dress with grey over the knee dressMiranda Kerr in grey and black tunic dress with over the knee black boots
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Vanessa Hudgens blue dress with grey over the knee boots

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Work is an environment where may be more concerned about your footwear selection. However, match the right dress to the right pair of over the knee boots and your professional style can be taken to the next level. Tunic style dresses with long or capped sleeves look great with these kinds of boots and make for effortless but well styled workwear. 

You’ll find it more practical to stick to a sturdy heel and basic colours, like a pair of black or grey over the knee boots, which you can match with complementary accessories with easily. The quality appearance of the shoes is also important for a professional setting; so, ensure they are well polished or covered, fit correctly, and do not gape too much above the knee. Then these beauties will be another option for those “I have nothing to wear” mornings and make a knee high boots outfit a work staple.

Over the Knee Boots in Summer

Candice Swanepoel street style in white long sleeved dress and grey over the knee bootsKarrueche Tran in red t-shirt dress and black over the knee boots
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Gigi Hadid black and white wrap dress with grey over the knee boots

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When the warmer months roll around, you can be more inventive with your footwear than flip flops by mixing it up with over the knee boots. T-shirt style dresses, wrap dresses, and floaty long-sleeved summer frocks complement this style of boots because of their shape and versatile materials.

Boots for summer can work despite the temperatures; they just need to have a breathable enough lining and enough room for movement. A flat knee high boots outfit can be worn throughout the seasons. Lighter shades tend to complement summer clothing more, however darker tones can work with vibrant colours too; especially for rooftop bars and vacation outings.

Over the Knee Boots in Winter

Zendaya striped sweater dress and black over the knee bootsJennifer Lawrence with brown trench coat, black polar neck dress and black over the knee bootsJennifer Lawrence with brown trench coat, black polar neck dress and black over the knee boots
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Wearing over the knee boots in winter presents a fabulous opportunity to take advantage of the extra material this style provides, and will also give your winter wardrobe some variety in the traditional boot department. Sweater dresses and turtle-neck dresses are chic and cosy options for winter and fall dressing, and the perfect combo for this type 0f shoe. You can afford to make these dresses and boots slightly longer, as long as you can break it up with a pattern or small gap. 

With the elements against you, pay close attention to care instructions, particularly if you wear suede over the knee boots. Do also ensure there’s enough space for some wool socks or thicker tights – you’ll thank us when the chill tries to get the better of you.  Finally, get creative with your winter boots and use them to add some intrigue to typical winter palettes.

What Dresses to Wear with Over the Knee Boots: Final Note

  • When it comes to everyday wear, go for floaty or fitted day dresses which complement the vibe of the pair of boots.
  • For the evening, cocktail length dresses paired with heeled over the knee boots make for gorgeous evening attire – just remember the rule of balance. Choose a thinner heel and well-proportioned lengths.
  • For work, tunic dresses with long or capped sleeves and over the knee boots are a professional ensemble ready to go. Keep your boots well-tended and fitted in smart suede or leather with a block heel.
  • In the summer, over the knee boots with breathable lining in lighter shades look great with wrap dresses and t-shirt dresses.
  • In the winter, enjoy the extra material on offer and style your boots with sweater dresses or polo neck dresses.

Still concerned about styling over the knee boots or nervous about trying on a pair? Watch the video below to be inspired. 

We hope you’re questioning any misgivings you may have had about over the knee boots and now have the answers on how to style over the knee boots with dresses. Try them on, you won’t regret it!

Read more great articles on women’s fashion here at alexie.

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