How to Wear Ankle Boots with Dress

6 min read
How to Wear Ankle Boots with Dress

How to wear ankle boots with dresses

Jeans with ankle boots? Meet dresses with ankle boots. Let’s match that skirt or dress with Blundstone’s best ankle boots and Chelsea boots. We have some tried and true ideas to help guide you.

Warm breezes and sunny days bring more style freedom. Our trendiest selves are inspired to include more color and to seek out the graceful movement of lightweight cottons and silks in mid-calf skirts, maxi dresses, and midi dresses of all cuts and kinds. For a chilly day or evening, a summertime sweater dress can work well with ankle boots or Chelsea boots. And this summers moto-boho chic look meets Mother Earth comfortably in a pair of Blundstones.

Outfit Ideas:

Wearing ankle boots with summer dresses and skirts requires attention to a few basics: Are you tall or petite? Do you want a boot with a high heel, low heel, or chunky heel? Are you after an edgy vibe or a casual look? Or a little of both? Perhaps you want a boot that can transition effortlessly from workday through an evening event.

Check the length of your skirt or dress to make sure it doesn’t cover or get caught in the top of your boots. Depending on your height and leg length, a space of 3 to 4 inches between boot top and dress hem will allow billowy dress fabric to move gracefully and for your Blundstones to be seen, whether you’re seated or standing.

Note that the tops of ankle boots fall just below the ankle, while Chelsea boots rise higher, a difference sure to influence the choices that continue to shape your own style. Because ankle boots are usually chunkier than Chelsea boots, you may want to pair them with different dress fabrics and lengths, or even a pair of light leggings and a shirt dress.

Do you have a denim dress that needs more personal attention? a little love? Flat ankle boots add style and refinement to a dressed-down denim look. For a bit more edginess, slip on a heeled ankle boot. Try a chiseled toe for a sleeker line or a rounded toe for a more casual look.

Try a full midi skirt or a trim shirt dress with a blazer for the office — or a denim jacket for a casual afternoon. Choosing between ankle boots and Chelsea boots will depend upon the line and length of your skirt, the way the boot makes your leg look longer — and always your personal taste. Here’s a good look: Pair a pencil skirt and blazer with Chelsea boots for a smooth and classic silhouette.

Which heel height do you want?

#062 Women's Dress Chelsea Boots

Classic and functional, lightweight and comfortable, this dress boot has a lean profile and chisel toe that moves from office to dinner in style. #062 is crafted of stout brown water-resistant leather with brown elastic side gore, TPU outsole, cushioned midsole, SPS Max Comfort system for outstanding shock absorption, and a removable footbed.

#1671 Women's Series Heeled Boots

This heeled ankle boot is comfortable, rugged, and very feminine. Its sleek design and contoured fit in soft, supple leather make sure this boot feels as good as it looks. #1671 is crafted of premium black water-resistant leather, with a 5cm Cuban heel, black elastic side gore, removable footbed and heel pad for best shock absorption, a cushioned midsole, and a steel shank for stability.

#2365 Women's Series High Heeled Boots

This all new Women’s High Heeled boot features a stable 7.62cm (3-inch) Cuban heel designed for chic and comfortable all-day wear. Made of premium water-resistant black leather, this boot has leather and synthetic lining, an Ortholite footbed with XRD® Technology for maximum comfort and shock absorption, Polyurethane outsole, and a TPU shank.

Original casual look and Classic edgy vibe


#500 Women's Originals Chelsea Boots

A truly iconic Blundstone, this lightweight boot is revered for its comfort and durability. Crafted of stout brown premium water-resistant leather, the Original #500 has an elastic side gore, TPU outsole, cushioned midsole, SPS Max Comfort system for outstanding shock absorption, removable footbed, and a steel shank for added stability.

#562 Women's Classics Chelsea Boots


This elegant boot delivers the good looks, comfort and durability that have made Blundstone legendary. Crafted of water-resistant leather, #562 has a contrasting elastic side gore, leather lining, TPU outsole, cushioned midsole, SPS Max Comfort system, removable footbed with XRD® Technology in the heel strike zone, and extra footbeds for a custom fit.

#585 Women's Classic Chelsea Boots

This flat ankle boot is a new version of our Blundstone Original. #585 is crafted of premium rustic brown water-resistant leather, with leather lining and brown elastic side gore, durable TPU outsole, cushioned midsole, SPS Max Comfort system, removable footbed with XRD® Technology in the heel strike zone for best shock absorption, and an extra set of footbeds for a custom fit.

Blundstones for office through evening


#1306 Women's Dress Chelsea Boots

This classic dress boot is as comfortable as it is durable. Crafted in premium rustic brown water-resistant leather, #1306 boasts a lean profile and chisel toe for seamless office to evening wear. Add to this a brown elastic side gore, durable TPU outsole, comfortable cushioned midsole, SPS Max Comfort system for superior shock absorption, and a removable footbed.

#1308 Women's Dress Chelsea Boots


Sleek, sturdy and comfortable all day long, #1308 is a dress boot with a lean profile and chisel toe. Fashioned of our signature rustic black premium water-resistant leather, this boot has a black elastic side gore, durable TPU outsole, comfortable cushioned midsole, SPS Max Comfort system for outstanding shock absorption, and a removable footbed.

#2060 Women's Series Heeled Boots


Sleek, rugged, and distinctly feminine, the #2060 heeled boot is crafted of water-resistant shiraz leather that becomes even softer and more supple as you wear it. Contoured fit and classic styling include a 5cm Cuban heel, black elastic side gore, removable footbed and heel pad for best shock absorption, cushioned midsole, a responsive and durable outsole, and a steel shank for dependable foot stability.



Effortless boho chic

Blundstone boot wearers always prove our value:

"I work in them, I walk around in them and probably could go to sleep standing in them because they’re that comfortable." - J.W.

What could be more effortless? We already love our Blundstones with our wide leg trousers and skinny jeans. Skirts and summer dresses more than meet this classic chic vibe with a pair of ankle boots or Chelsea boots. Blundstones make your legs look a bit longer and make your boho style expression a lot stronger.