As much as we adore a traditional heel with an LBD or bold sneakers with a nap dress, pairing dresses with boots is one of our favorite outfit formulae. Depending on our mood or the occasion, we may go as formal or informal, classic or current, as we choose. In fact, we went to street style heroes to show the adaptability of wearing dresses with boots, which may be perfect for every season. So whether you're wanting to create some balance with a tiny dress and thigh-high boots or play up the contrast between a delicate slip dress and edgy combat boots, keep scrolling for 11 dresses and boots combinations that we can't get enough of.
Denim Dresses and Metallic Boots
Denim isn't just for jeans and jackets. Here, fashion influencer Emilie Joseph combines her denim midi dress with slouchy silver boots. If you're seeking for statement shoes that can also act as neutrals, metallics are it.
Slip Dresses and Combat Boots
‘90s 'fits are still going strong, as the comeback of slip dresses has infiltrated into our closets. From our experience, the lingerie-esque garment is best worn contrasting its delicate and feminine vibe with dirty bike or combat boots. They provide a much-needed edge to a delicate shape and may or may not have you feeling like you’re in an Olivia Rodrigo music video.
Sheer Dresses and Tall Leather Boots
Sheer dresses take seductive to the next level. The skin-baring, cheeky appearance works especially well for those late nights out, but it doesn’t have to primarily be worn with heels. This is when the incorrect shoe idea comes into play: Add a degree of casualness—and coverage—with a pair of tall leather boots, letting your shoe of choice show through the mesh fabric.
Floral Dresses with White Chelsea Boots
Floral dresses are one of our favorite summer essentials. Still, you can adjust yours to shoulder seasons with the correct footwear, like these white Chelsea boots. Darker flowers that combine white work for both spring and fall.
Dresses With Slits and Thigh-High Boots
For those who appreciate the sheer trend, cutout dresses are likely a mainstay in their closet. However, if stilettos or strappy sandals no longer seem to do the trick, thigh-high boots might add a sumptuous touch. This is especially true if the dress has a high slit, which just adds to the already-dramatic outfit.
Midi Dresses and Ankle Boots
Pairing colors together may seem like a decision guaranteed to clash, but don’t be afraid to add even more color to an already strong outfit. An ankle boot gives a comfortable and attractive choice for enhancing those brilliant hues without going crazy. Experiment with different designs and make a statement with this perennial classic.
Shirt Dresses with Knee-High Boots
Make a pristine shirt dress seem even more stylish in the office by playing around with proportions. If you’re working in a basic itty bitty button-down, throw on a pair of knee-hitting leather boots.
Read Also: Top Styles of Dresses to Wear with Cowboy Boots
Oversized Shirts with Slouchy Boots
If you’re into experimental fashion, a slouchy boot could just be the right complement to your ensemble. To pull off this style, consider matching it with an oversized shirt that serves as a dress. Depending on the length of your dress and the shaft of your boots, it might appear like you're wearing jeans or pantaleggings.
Neutral Hues with Animal Print Boots
If your color palette of the day is more subdued, liven up your outfit with a pair of embossed boots. We’re especially fond of a snakeskin pattern, and whether you select bright neons or toned-down neutrals, it’ll provide a much-needed texture and vibrance to your outfit. Thankfully, with the progress of technology, there are plenty of ethical solutions to select from.
Babydoll Dresses with Cowboy Boots
Emma Chamberlain is on to something here. She fashions her yellow babydoll dress with red cowboy boots—and it'll eternally live on our outfit mood board. A babydoll dress, both tiny or midi forms, may bring a fun and feminine mood to the western silhouette.
Tove Svendson 
As much as we adore a traditional heel with an LBD or bold sneakers with a nap dress, pairing dresses with boots is one of our favorite outfit formulae. Depending on our mood or the occasion, we may go as formal or informal, classic or current, as we choose. In fact, we went to street style heroes to show the adaptability of wearing dresses with boots, which may be perfect for every season. So whether you're wanting to create some balance with a tiny dress and thigh-high boots or play up the contrast between a delicate slip dress and edgy combat boots, keep scrolling for 11 dresses and boots combinations that we can't get enough of.
Denim Dresses and Metallic Boots
Denim isn't just for jeans and jackets. Here, fashion influencer Emilie Joseph combines her denim midi dress with slouchy silver boots. If you're seeking for statement shoes that can also act as neutrals, metallics are it.
Slip Dresses and Combat Boots
‘90s 'fits are still going strong, as the comeback of slip dresses has infiltrated into our closets. From our experience, the lingerie-esque garment is best worn contrasting its delicate and feminine vibe with dirty bike or combat boots. They provide a much-needed edge to a delicate shape and may or may not have you feeling like you’re in an Olivia Rodrigo music video.
Sheer Dresses and Tall Leather Boots
Sheer dresses take seductive to the next level. The skin-baring, cheeky appearance works especially well for those late nights out, but it doesn’t have to primarily be worn with heels. This is when the incorrect shoe idea comes into play: Add a degree of casualness—and coverage—with a pair of tall leather boots, letting your shoe of choice show through the mesh fabric.
Floral Dresses with White Chelsea Boots
Floral dresses are one of our favorite summer essentials. Still, you can adjust yours to shoulder seasons with the correct footwear, like these white Chelsea boots. Darker flowers that combine white work for both spring and fall.
Dresses With Slits and Thigh-High Boots
For those who appreciate the sheer trend, cutout dresses are likely a mainstay in their closet. However, if stilettos or strappy sandals no longer seem to do the trick, thigh-high boots might add a sumptuous touch. This is especially true if the dress has a high slit, which just adds to the already-dramatic outfit.
Midi Dresses and Ankle Boots
Pairing colors together may seem like a decision guaranteed to clash, but don’t be afraid to add even more color to an already strong outfit. An ankle boot gives a comfortable and attractive choice for enhancing those brilliant hues without going crazy. Experiment with different designs and make a statement with this perennial classic.
Shirt Dresses with Knee-High Boots
Make a pristine shirt dress seem even more stylish in the office by playing around with proportions. If you’re working in a basic itty bitty button-down, throw on a pair of knee-hitting leather boots.
Read Also: Top Styles of Dresses to Wear with Cowboy Boots
Oversized Shirts with Slouchy Boots
If you’re into experimental fashion, a slouchy boot could just be the right complement to your ensemble. To pull off this style, consider matching it with an oversized shirt that serves as a dress. Depending on the length of your dress and the shaft of your boots, it might appear like you're wearing jeans or pantaleggings.
Neutral Hues with Animal Print Boots
If your color palette of the day is more subdued, liven up your outfit with a pair of embossed boots. We’re especially fond of a snakeskin pattern, and whether you select bright neons or toned-down neutrals, it’ll provide a much-needed texture and vibrance to your outfit. Thankfully, with the progress of technology, there are plenty of ethical solutions to select from.
Babydoll Dresses with Cowboy Boots
Emma Chamberlain is on to something here. She fashions her yellow babydoll dress with red cowboy boots—and it'll eternally live on our outfit mood board. A babydoll dress, both tiny or midi forms, may bring a fun and feminine mood to the western silhouette.