How to Wear Knee-High Boots with Dresses: Midi, Mini, & More!

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Knee-high boots can take a feminine look like a dress and jacket, giving it a slight masculine twist. While we all love our ballet flats and espadrilles, knee-high boots can add a new dimension to your dresses.

1. Versatile Styling: Pairing Knee-High Boots with Leggings or Opting for Bare Legs

If you want to add a quirky twist or show off your personality, add a pair of fun leggings underneath your knee-high boots.

Charlize Theron dazzles with bare legs and knee-high boots paired with a glittering mini dress, contrasting Reese Witherspoon's cozy style featuring leggings and sleek knee-high bootsCharlize Theron dazzles with bare legs and knee-high boots paired with a glittering mini dress, contrasting Reese Witherspoon’s cozy style featuring leggings and sleek knee-high boots (Credit: WENN)

You must ensure that the color and design match your chosen dress.

Perfect Ensemble: Rag & Bone's Cherie mini sweater dress, complemented by HUE's Ultra leggings and the elegance of Easy Spirit's Reverie knee-high bootsPerfect Ensemble: Rag & Bone’s Cherie mini sweater dress, complemented by HUE’s Ultra leggings and the elegance of Easy Spirit’s Reverie knee-high boots

Although tights and socks are a staple, knee-high boots with bare legs can be the perfect choice for dresses with a mini-skirt silhouette.

2. Elegance Meets Comfort: Midi Dresses with Knee-High Boots

Midi dresses are perfect for wearing knee-high boots, as the fabric will cover the top of your boots.

Style Icons Unite: Olivia Palermo, Myleene Klass, and Kate Bosworth masterfully combine knee-high boots with chic midi dresses for a sophisticated lookStyle Icons Unite: Olivia Palermo, Myleene Klass, and Kate Bosworth masterfully combine knee-high boots with chic midi dresses for a sophisticated look (Credit: Avalon / Instar / WENN)

If you do not like exposed skin, this dress silhouette will create a more seamless and elegant look.

Elegance Redefined: Vince's diagonal ribbed sleeveless midi dress meets the modern flair of AMI Paris block-heel knee-high bootsElegance Redefined: Vince’s diagonal ribbed sleeveless midi dress meets the modern flair of AMI Paris block-heel knee-high boots

Most midi dresses will cover the first few inches of your boots, keeping your legs warm while making your boots a little more wearable.

3. Chic and Bold: Transform Your Look with Blazer Dresses and Knee-High Boots

Fashion Powerhouses: Kelly Rowland, Taylor Swift, and Nicole Scherzinger stun in trendy blazer dresses, perfectly paired with knee and thigh-high bootsFashion Powerhouses: Kelly Rowland, Taylor Swift, and Nicole Scherzinger stun in trendy blazer dresses, perfectly paired with knee and thigh-high boots (Credit: Lia Toby / Avalon / WENN)

If you’re looking for a sexier look, take a leaf from the Kardashian-Jenner styling book and wear your shoes with a blazer dress.

Fusion: The Jay Godfrey Ace blazer dress, adorned with a dazzling sequin collar, elegantly pairs with the edgy Paris Texas 100mm crocodile-effect knee-high bootsFusion: The Jay Godfrey Ace blazer dress, adorned with a dazzling sequin collar, elegantly pairs with the edgy Paris Texas 100mm crocodile-effect knee-high boots

Knee-high boots are perfect for showing off your legs and a fresh tan. Wearing a shorter dress can help elongate your legs by flashing a little extra skin.

4. Classic Harmony: Knee-Length Dresses Complemented by Knee-High Boots

Classy Trio: Kelly Brook, Ashley Roberts, and Hilary Duff elegantly match knee-length dresses with stylish knee-high boots for a timeless lookClassy Trio: Kelly Brook, Ashley Roberts, and Hilary Duff elegantly match knee-length dresses with stylish knee-high boots for a timeless look (Credit: Avalon / WENN)

Knee-length dresses go hand-in-hand with this style of boots, as the hem of your dress will skirt the top of your boots.

Sophisticated Elegance Meets Bold Attitude: The M.M. LaFleur Hayden dress beautifully contrasts with the striking Sam Edelman Clarem snake bootsSophisticated Elegance Meets Bold Attitude: The M.M. LaFleur Hayden dress beautifully contrasts with the striking Sam Edelman Clarem snake boots

Don’t be afraid to wear a bolder style of knee-high boots to the office, especially with a knee-length dress. A knitted dress can help get a simple base to complement your shoes and make them pop.

5. Bohemian Rhapsody: Embracing the Free Spirit with Floral Dresses and Knee-High Boots

Fans of the bohemian style aesthetic reach for knee-high boots more than most people.

Bohemian Elegance: Britney Spears and Myleene Klass showcase their unique flair in floral dresses paired with knee-high boots for a touch of whimsyBohemian Elegance: Britney Spears and Myleene Klass showcase their unique flair in floral dresses paired with knee-high boots for a touch of whimsy (Credit: Mario Mitsis / Avalon.red / WENN)

A floral print dress is a great way to juxtapose feminine and masculine elements to create a contemporary look with a vintage twist.

Bohemian Charm Meets Rugged Sophistication: The Johnny Was Ciara floral-print dress with slip is exquisitely paired with the robust Frye Melissa button lug bootsBohemian Charm Meets Rugged Sophistication: The Johnny Was Ciara floral-print dress with slip is exquisitely paired with the robust Frye Melissa button lug boots

If you opt for this style, brown leather boots are a softer alternative to traditional black knee-high boots.

6. The Finishing Touch: Choosing the Right Socks for Your Knee-High Boots

Most people choose to wear socks with their knee-high boots, even if they’re hidden under the shoes.

Cozy and Chic: Geri Halliwell and Myleene Klass demonstrate how tights and socks can add comfort and style to knee-high bootsCozy and Chic: Geri Halliwell and Myleene Klass demonstrate how tights and socks can add comfort and style to knee-high boots (Credit: Karl Piper / WENN)

Wearing socks or tights will help absorb the moisture in your feet and reduce odor while making walking around in your boots easier for longer.

You can even experiment and add fishnets or logo-embossed tights with your knee-high boots for a sexier look.

Urban Elegance Meets Comfort: The chic All Saints Fey Leppo dress paired effortlessly with Bloch Contoursoft footed tights and fashionable Caverley Candy slouchy leather knee bootsUrban Elegance Meets Comfort: The chic All Saints Fey Leppo dress paired effortlessly with Bloch Contoursoft footed tights and fashionable Caverley Candy slouchy leather knee boots

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