How to Wear Your Favorite Boots with a Dress

Boots and dresses are one of fall’s most timeless pairings—but the key to pulling them off lies in balance and proportion. Whether you love a sleek knee-high or a western-inspired cowgirl boot, the right combination of shapes, fabrics, and silhouettes can make your outfit feel cohesive and effortless.

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Here are six easy ways to style boots with dresses using some of our favorite pieces from Mae Threads.

1. Sleek Knee-High Boots + Figure-Hugging Sweater Dress

Pieces: The Attie Dolman Sleeve Sweater Dress in Oatmeal + Black Heeled Boots (Target)

The Attie Dress’s ribbed knit and wrap silhouette create long, unbroken lines that pair beautifully with the sleek finish of knee-high boots. The close-fitting fabric and elongating V-neck make this combo feel polished and subtly sophisticated.

Styling tip: Keep accessories minimal—a belt can define your waist, but avoid bulky layers that compete with the dress’s curve-hugging shape.

2. Sleek Knee-High Boots + Knee-Length Dress

Pieces: The Jena Plaid Dress in Burgundy + Blush Knee-High Boots (DSW)

Knee-length dresses like the Jena Plaid Dress hit that sweet spot for showing off taller boots. The structured cotton and sweet gingham pattern balance the sleek, streamlined shape of the boots, creating a feminine-meets-tailored look that feels fresh and fall-ready.

Styling tip: Try choosing boots in a soft or unexpected color (like blush or taupe) to lighten the look and draw attention to your legs.

3. Ankle Boots + Structured Midi Dress

Pieces: The Cloverfield Denim Dress + Cream Booties (Target)

The Cloverfield Dress is a perfect example of structured ease—its crisp denim fabric and defined waist pair beautifully with ankle boots that ground the outfit without overwhelming it.

Styling tip: If the dress and boots are contrasting colors, add socks in a tone between the two to visually connect them and soften the transition.

4. Ankle Boots + Flowy Maxi Dress

Pieces: The Eden Dress in Red + Tan Booties (Boot Barn)

The airy, romantic drape of the Eden Dress works best with streamlined ankle boots that keep the outfit grounded. The midi-to-maxi length lets just enough of the boots peek out for balance, while the fitted bodice keeps the proportions flattering.

Styling tip: Add a denim jacket or cropped cardigan to emphasize your waistline and break up the volume.

5. Cowgirl Boots + Voluminous Maxi Dress

Pieces: The Sadie Tiered Midi Dress + White Western Boots (Altar’d State)

The playful tiers and ruffles of the Sadie Dress are made for a western moment. White or light-toned cowgirl boots keep the look fresh and whimsical.

Styling tip: Since this pairing already has plenty of movement, keep accessories simple—a dainty pendant or wide-brim hat completes the look without overwhelming it.

6. Cowgirl Boots + A-Line Midi Dress

Pieces: The Mickie Velvet Embroidered Dress in Emerald + Tan Western Boots (Boot Barn)

The Mickie Dress brings together bohemian embroidery, soft velvet texture, and a gently flared A-line shape—perfect for dusting the top of classic tan cowgirl boots. The structured hem of the A-line skirt contrasts beautifully with the rounded shape of the boots, keeping the silhouette balanced.

Styling tip: Add a belt or cropped jacket to emphasize your waist and create a flattering proportion between the volume of the skirt and the height of the boots.

Each of these looks balances structure, length, and texture in a way that feels intentional and wearable. The key is proportion:

• Fitted dress = Sleeker boot
  
• Voluminous dress = Chunkier or western boot
  
• Midi lengths = Best for showing ankle boots
  
• Knee lengths = Perfect for tall boots
  

With just a few thoughtful combinations, you can make your boots and dresses feel effortlessly cohesive all season long. And you can’t go wrong with a Mae Threads dress!