Wearing boots with dresses during the winter is an easy way to stay warm while looking super chic! I personally love to wear boots with a dress, but I know it may be new to some of you. So, I’m sharing a few simple ways to wear boots with a dress that will have you feeling stylish, confident, and warm this winter. During the last few months of winter, it can be easy to just throw whatever on to feel warm and cozy. But the right dress with a pair of boots can make you look and feel put together despite the weather (and with very little effort!). Find some chic ways to wear boots with dresses without compromising comfort below…
By the way, if you’re looking for how to wear boots with jeans, make sure you check out this post too!
12 Ways to Wear Boots with a Dress
#1) Ivory Mini Dress with Knee-High Boots
The first dress and boots outfit idea is…a mini dress with knee high boots! This is s super simple combo. I personally love my legs so I don’t mind that this look shows a little leg. But if you like to keep your legs covered, don’t worry…there rest of the looks have you covered (literally)! Because this dress is short, the length is easier to style with boots and you can get away with pretty much any style boot…ankle, knee-high, combat, sock booties, etc. This is something I’d wear for a winter day in Texas, but not necessarily a winter day in Colorado. If you like the idea of a mini dress with knee-high boots, consider adding black tights for extra warmth. Throw on an oversized teddy coat, some of your favorite everyday jewelry, and and you’re ready to go!
By the way, I shared 7 ways to style the teddy coat I’m wearing above in this post in case you’re interested!
#2) Black Midi Dress with Mid-Calf Boots
Next up is a sexy option that you can pull out for those winter date nights! This ASTR The Label dress is a sexy show-stopper! The longer length is ideal for women over 40 but I love the fitted silhouette and strappy cutout details on the bust. By the way, you don’t need this exact dress to recreate this outfit…take inventory of your closet to see if you have piece that will help you recreate the look!
Since it’s more fitted and the hemline fits closer to the leg, picking out a pair of boots can be a little trickier. For example, wearing a pair of knee-high boots would show underneath the fitted dress. Insead, go with a shorter boot. I styled it with a pair of older mid-calf boots by Paige. But you could also wear ankle boots, Chelsea boots, or sock booties. By the way, adding a coat or jacket to any of these looks will help with that warmth factor, but depends on your climate. Play around with your third layer if need be.
#3) Maxi Sweater Dress with Combat Boots
With a flowy maxi dress, anything goes. You can wear knee high boots, ankle boots, sock boots…or combat boots! This look might be a little out of your comfort zone but I love the way combat boots look with dresses because you’re mixing those feminine and masculine styles. This is an older brown sweater dress that has a small slit on the side. I’ve linked some similar options for you. The combat boots are some of my favorite by See by Chloe. I wear these boots with jeans, skirts, and dresses and always love how they look! This look is a little more casual so I’m sharing a way to dress up the exact same dress below…
#4) Brown Maxi Dress with Black Knee-High Boots
This is the exact same dress from the look above, but this time I’m wearing some gorgeous Schutz knee high boots. I have these boots in three colors…white, black, and python print. They are my go-to boots when I want to dial it up a notch. And they’re a wonderful price point for the quality and versatility! The slit in this dress really shows off the shoes but even if it didn’t have a slit, the knee-high boots would still work.
#5) Black Midi Dress with Brown Knee-High Boots
This look is very similar to #4 but the colors are just switched. In this look, I’m wearing a black midi dress with brown knee-high boots. This look keeps me completely covered and super warm. With the length of this dress, I could also wear ankle boots, but I’d probably avoid mid-calf boots because the amount of skin between the top of the boots and the bottom of the hemline wouldn’t be large enough.
#6) Floral Midi Dress with Heeled Ankle Boots
I love the way floral dresses with boots look during the fall and winter! This floral dress is more muted and in a darker color so it’s more wearable for winter. Plus it has sleeves and a modest neckline. I styled it with some gorgeous black Isabel Marant ankle boots. These are a little higher than traditional ankle boots but they work really well with the length of this dress on me. You could also wear some black knee-high boots.
#7) Mini Dress with Ankle Boots
For this look, I’m wearing the same black ankle booties with a shorter mini dress by BB Dakota. To winterize the look, I added tights and a leather blazer. You could also wear mid-calf boots or knee-high boots with this look too!
#8) Colorblock Midi Dress with Knee-High Boots
This was one of my favorite outfits from last year! This dress is so gorgeous, comfortable, and flattering! It’s more fitted toward the bottom, but I really loved the way the knee-high boots worked with this dress. If you’re going to go with knee-high boots on a look like this, I’d stick to a similar color to the dress so that it keeps an elongating line. You could also wear ankle boots.
#9) Floral Mini Dress with Knee-High Boots
This is another way to style a fun mini dress with knee high-boots (like I did in #1). For this look, I’m wearing a bright pink printed dress, oversized cardigan, and the same Schutz boots I’ve featured in a few looks…but in white! I could also see myself swapping these boots for a pair of brown or ivory block heel ankle booties.
#10) Tailored Sheath Dress with Ankle Boots
This look is a great example of how you could style your dress and boots for the office. A more fitted, tailored sheath dress is a popular workwear piece so I wanted to show you how you can wear it with boots. I went with some square-toes ankle boots by Vince but you could wear any black booties you have. With the length of this dress on me, I would avoid knee-high boots because the amount of skin between the bottom of the dress and the top of the boot would be too small.
#11) Printed Maxi Dress with Slouchy Boots
If you have a flowy, printed maxi dress, you can style it with any style boot you want! With this older Saloni dress, I opted for some brown slouchy boots but you could wear some sexy stiletto boots, ankle booties, sock boots, etc.
#12) Silky Maxi Dress with Black Ankle Boots
I LOVE this look from our trip to Europe in 2021! The silky Zadig & Voltaire dress is the perfect combination of sexy and sophisticated. To keep that sexy sophistication, opt for boots that are more classic and streamlined like the pair I chose. I could also probably wear some black knee-high boots like the pair by Schutz I’ve featured. But the goal is to go with a slender heel, no slouching, etc. to keep that classic look.
Best Dresses To Wear With Boots
The best dresses to wear with boots will depend a lot on your personal style, your body shape, and your height. If your petite, midi dresses may be maxi dresses. If you’re tall, some mini dresses might feel too short on you. An A-line dress might be better for your body than a fitted dress depending on your body shape. You get my point! Whatever your preference, you can shop my favorites featured in the above graphic below. I tried to feature dresses that will 1) transition into spring with a simple swap of heels, sandals, or sneakers and 2) are super versatile so you can wear them for lots of different occasions (think weddings, errands, lunch with friends, date night, etc.).
If you don’t know your body shape, this post is a must-read.
Do you like wearing boots with dresses? Let us know your favorite way to wear them in the comments at the very bottom of this post!
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