If there’s one closet staple that I pretty much live in year-round, it’s a dress. Contrary to popular belief, this one-piece outfit can be worn throughout many seasons—as long as you know how to style it right. It’s not just reserved for hot summer days (although it’s a great choice then too!) Pair a dress with some sandals and a denim jacket during warmer occasions or sneakers and a long cardigan on crisp fall days. Either way, you’re guaranteed to look polished and ready for anything.
One universally loved way to style a dress is with a pair of boots. Whether you love ankle boots, tall boots, or cowboy boots, I know firsthand that it can feel a bit intimidating to combine them with a dress. However, with that being said, the duo makes for such a classic and feminine look. Plus, it doesn’t get much easier than throwing on a little sun dress and slipping into some comfy boots.
From elegant evening looks to effortlessly chic daytime styles, I’m sharing exactly how to wear boots with dresses—regardless of the occasion or vibe you’re going for.
How to Wear Boots With Dresses
White Western Boots With a Babydoll Dress
A flowy dress and western boots make for an undeniably charming combo (and yes, you can wear this even when you aren’t traveling in Nashville.) This green floral babydoll dress paired with white western boots and a straw cowboy hat is perfect for concerts, a backyard barbecue, or any sunny day, really. I love how the puff-sleeved dress and more laid-back accessories effortlessly blend “cute” with “casual.”
The straw hat adds a touch of fun and serves as a statement piece, pulling the character of the boots and the accessories together. Take things up a notch and elevate this look even further with your favorite bag and some dainty gold jewelry.
Metallic Boots With a Mini Dress
Heading somewhere special? Dress things up a bit with this classy black and gold look. Pairing these fun boots with a black tweed mini dress, some oval-shaped sunglasses, and a sleek hair bow creates an outfit that’s both sophisticated and eye-catching.
The boots add a glamorous feel, making this an ideal outfit choice for any occasion when you want to stand out. For the finishing touches, add your favorite statement jewelry, like some dangly earrings or chunky bracelets.
Western Boots With a Maxi Dress
If you need an outfit that transitions seamlessly from day to night, this is it. These statement two-tone cowboy boots are major showstoppers, and paired with a flowy maxi dress and a leather jacket, they make for a great, go-to outfit. Whether you’re heading out for lunch or you’re going to a special event, this look provides a laid-back feel in a stylish and timeless way.
Western Boots With a Mini Dress
If you’re searching for a fool-proof summer look, consider styling a simple mini dress with some western boots. I’ve been obsessed with these brown leather cowboy boots lately and think they’d actually pair well with a variety of outfits. To really hit home with the warm weather vibes, opt for a butter yellow dress, which has proven to be very much on trend lately.
Need a layer? Throw a denim jacket over your shoulders in case it cools down, then complete your outfit with a cute tote bag and some understated accessories.
Heeled Boots With a Shift Dress
One of my personal favorite ways to style a dress with boots? Pairing tall or over-the-knee varieties with a short dress. This combo creates a tried-and-true look, and I love that you can add or take away layers depending on the weather you’re dressing for.
I typically reach for this outfit during the transitional months, like between summer and fall or winter and spring. I love layering with long cardigans because they’re not only practical but they also can provide a lot of dimension. Oh, and accessorizing with a belt is a great way to add some shape back into a layered look, so don’t be afraid to play around with different styles.
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