CURRENT AIR

The Dress Edit

I’m A Fashion Editor And This Is How I Style My Fall Dresses With Boots

 

This fall, dresses with boots are my go-to formula for effortless seasonal style. Indeed, it’s the perfect combination of cozy and chic, offering endless ways to switch things up. Whether you prefer a sleek knee-high boot or something chunky and bold, pairing designer boots with your favorite trendy dresses can transform any look. Furthermore, the two offer limitless combinations—ultimately keeping your wardrobe fresh and modern.

 

1. My Favorite: Thigh-Highs

 

At the top of my list is a no-brainer: knee-high boots. These classics are a fall essential, especially when paired with dresses that hit just above or below the knee. Moreover, this combination elongates the legs and creates a balanced silhouette that’s perfect for everything from brunch to date night. For this look, find a mini like the Lovers and Friends Caddie dress to pair with thigh-highs like Chloé’s Eves. Chloé will always be the best brand for fall dresses with boots.

CURRENT AIR Ruffled Mini Sweater Dress

Standing before a textured, abstract backdrop, a person holds a chic top handle evening bag. They are dressed in the ULLA JOHNSON Celia Pleated Paisley-Print Wool-Blend Twill Midi Dress, which features a long, floral pattern with long sleeves. Black high-heeled shoes with ankle straps complete the ensemble, and its warm tones beautifully complement the earth-toned background.

ULLA JOHNSON Celia Pleated Paisley-Print Wool-Blend Twill Midi Dress

By Texture & Color

 

2. Texture Play with Leather

 

Another fan favorite for fall dresses with boots is quite obvious. For those who love playing with textures, leather boots are an absolute game-changer. Mixing the rich texture of leather with different fabrics—knit or velvet—is a simple way to make a statement. However, I personally love pairing a sleek leather boot with Altuzarra’s Denning midi for an elegant vibe or Ulla Johnson’s Celia midi for a more bohemian feel. Just be sure to choose a leather boot that stands out—like these Paris Texas stilettos.

 

3. Color Blocking

 

Fall dresses with boosts aren’t just about neutrals; they offer the perfect opportunity to play with color. Color-blocked outfits add a modern twist to classic fall fashion, instantly updating your wardrobe. I’m all about pairing vibrant boots with simple silhouettes, like a red velvet Ralph Lauren dress for an unexpected pop of color. While you would normally pair this with a pair of black boots, reach for Balenciaga’s gold Cagoles instead—color-blocking is the way to go.

The Best Dresses To Pair With Boots

  • ISABEL MARANT Slayae Dress

    $770
  • ISABEL MARANT Felie Short Dress with English Embroidery

    $770
  • ISABEL MARANT Galia Dress in Plain-Colored Cotton Voile and Lace

    $825
  • ISABEL MARANT Dulce Viscose Short Dress

    $690
  • ISABEL MARANT Dalida Smocked Dress in Printed Cotton Voile

    $695
  • PRADA Pinstripe Silk Back Wool Mini Dress

    $2,600
  • ISABEL MARANT Selma Dress

    $1,790
  • DIANE VON FURSTENBERG Eloise Dress

    $418
  • DIANE VON FURSTENBERG Gizelle Jacquard Dress

    $538
  • DIANE VON FURSTENBERG Astrid Wool-Cashmere Wrap Dress

    $558
  • CURRENT AIR Laraline Paisley Jacquard Midi Dress

    $155
  • CURRENT AIR Ruffled Mini Sweater Dress

    $138
  • BLACK HALO Roanna Sheath Dress

    $415
  • BARDOT Lorel Midi Dress

    $129
  • AFRM Kay Long-Sleeve V-Neck Mesh Maxi Dress

    $128
  • ISABEL MARANT Albini Gathered Printed Silk-Blend Midi Dress

    $1,390
  • FREE PEOPLE In The Garden Mini Dress

    $248
  • FREE PEOPLE Sunkissed Mini Dress

    $168
  • FREE PEOPLE Hampton Mini Dress

    $168
  • ULLA JOHNSON Celia Pleated Paisley-Print Wool-Blend Twill Midi Dress

    $750
  • LOVERS AND FRIENDS Caddie Mini Dress

    $138

By Length & Heel

 

4. Classic Pointy Booties

 

Aside from knee-highs, I’m also loving fall dresses with pointy boots—specifically booties. There’s something timeless about a pair of pointy-toe footwear, especially when paired with maxis. Moreover, they add a sleek and sophisticated edge to any outfit, making them my top choice for workwear or evening outings. A beautiful pair to take a peek at is the Christian Louboutin So Apostrohpa boots and Dôen’s Oliana maxi. Classic pointy booties never disappoint—they’re an absolute wardrobe staple.

 

5. Chunky & Ultra-High

 

For those days when you want to go bold, chunky, ultra-high boots are the way to go. However, this season, I’m all about pairing these standout boots with shorter, structured dresses to create a powerful silhouette. Think of a mini like this Saint Laurent velvet dress to balance out the chunkiness of boots like this pair from Bottega Veneta. Styling fall dresses with boots has never been more exciting than with these eye-catching options that redefine the fall wardrobe.

Shop All Dresses

A person stands joyfully against a light-colored wall, wearing the FREE PEOPLE Hampton Mini Dress with full sleeves and a ruffled hem. They have long hair, knee-high black boots, and are gracefully holding an elegant top handle evening bag.

FREE PEOPLE Hampton Mini Dress

Wearing the FREE PEOPLE In The Garden Mini Dress adorned with a blue ribbon, paired with brown boots and carrying a top handle evening bag, a person stands in a lavender field. The scene is complemented by the backdrop of lush green trees beneath a cloudy sky.

FREE PEOPLE In The Garden Mini Dress

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