12 Ways to Wear Boots with a Dress This Winter

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!


Ways to Wear Boots with a Dress This WinterWays to Wear Boots with a Dress This Winter

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!

Black Midi Dress with Mid-Calf Boots

#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.

Maxi Sweater Dress with Combat Boots Combat Boots

#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…

Brown Maxi Dress with Black Knee-High Boots

#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.

Ways to Wear Boots with a Dress This Winter

#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.

Floral Midi Dress with Heeled Ankle Boots | Ways to Wear Boots with a Dress This Winter

#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.

Mini Dress with Ankle 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!

Colorblock Midi Dress with Knee-High Boots

#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.

Ways to Wear Boots with a Dress This Winter

#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.

Tailored Sheath Dress with Ankle Boots

#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.

Printed Maxi Dress with Slouchy Boots

#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.

Silky Maxi Dress with Black Ankle Boots

#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

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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Little Black Dress

You really can’t go wrong with black dresses. I have this exact Alice + Olivia dress in hot pink and LOVE the fit. For winter, try some chic knee-high boots, classic leather ankle boots, or even a pair of black pointed-toe sock booties to dress it up.

Casual Striped Dress

With mini dresses, you can choose to wear pretty much any style of an ankle boot. I love this casual Line & Dot dress because stripes (especially horizontal) are very on trend right now, the length is really nice, and it’s warm but not TOO warm so you can still wear it on cooler spring days. Oh, and it’s under $120! To keep casual dresses casual, consider sticking with a shorter ankle boot or combat boot. To dress it up, go with a knee-high boot or heeled ankle boots.

Short Floral Dress

I’m not a huge fan of floral prints but I LOVE the way boots look with floral dresses. Ulla Johnson makes some of the prettiest prints and this dress will be perfect for the remainder of winter and into spring. Don’t forget that adding tights or a long coat can make some of your neutral “spring-like” dresses very wearable for winter! The same “boot rules” apply to this mini dress. I’d probably wear it with some white or brown ankle boots and an oversized teddy coat to winterize it!

Fun Fringe Mini Dress

Finge is really having a moment! This Line & Dot dress is SO cute and the perfect way to add some texture to a look. I’d style it with some white or beige ankle or knee-high boots and an ivory coat for a beautiful monochromatic winter white look!

Classic But Casual Midi Dress

This is the kind of dress every woman needs in her closet! It’s the perfect mix of casual and dressy depending on your accessory choices. And it’s by Rag & Bone, so you know it’s high quality and will last for years! Considering the length and the more fitted bottom, I’d opt for some sort of ankle or combat boots but avoid knee-high boots.

Elevated Black Slit Dress

This is the kind of dress you can really show off a killer pair of shoes! Since it has a slit, you can go with whatever style of boot you prefer. By the way, this dress is a great basic option if you’re looking for a versatile (but elevated) black dress for winter. Susana Monaco makes pieces in wonderful, luxe fabrics that are stretchy and comfortable.

Versatile Navy Midi Dress

This navy Tory Burch midi will look beautiful for the rest of winter but will also look beautiful in spring! I would style it with knee-high boots or ankle boots depending on where the dress hits on your legs. But you can probably get away with any kind of boot style. You just want to avoid a too-small sliver or skin showing between the bottom of the dress and the top of the boot.

Midi Dress to Dress Up Or Down

This fun, funky printed midi dress has a sexy slit, so it would work beautifully with a knee-high boot like the Schutz boots I featured in look #4. But if you want to dress it down a little, try the dress with ankle boots instead.

Beautiful Printed Midi Dress

Ulla Johnson does it again with another gorgeous, printed dress! This one is a little dressier than #3 and would be beautiful for a wedding or special event. It looks like it’s the perfect length so you can get away with any style of boot you prefer.

Sexy Silky Maxi Dress

This classic but silky dress by Vince would look beautiful with a pair of black, heeled ankle booties and a leather jacket for date night! But since it’s not as fitted at the bottom and has that A-line shape, you can get away with knee-high boots too.

Romantic Silky Dress

If you like the look of the last dress but want something with a little more coverage, this Vince dress has sleeves, a tie-waist, and can easily be dressed up or down. It’s also a beautiful option if you like a more romantic feel in your maxi dresses. Wear this with any kind of boots or booties you want.

Versatile Printed Maxi Dress

You all know how much I love a pink dress and this one by Misa is so beautiful. It’s a dark enough print to wear during winter, but also bright enough to wear during the spring! You could wear it to lunch with whatever boots you prefer or with heels to your next event.
Join the Conversation

12 thoughts on “12 Ways to Wear Boots with a Dress This Winter

  1. I love everything about this post. Can you do another where there are actual tights involved? I would never ever dream of going out without tights in the winter. Literally there are only like 4 days in Chicago where you can wear bare legs and a sweater dress.

    1. So happy you enjoyed the post, Trish! We will definitely add it to the list of posts coming up…thanks for the great idea! ~Team Busbee

  2. Hi! Any info on the earrings in look #4 under 12 Ways to Wear Boots with a Dress This Winter? The one with the brown dress and black boots shot in the hallway. Those earrings are beautiful bursts of diamond crystal magic! Thanks!

    1. So glad you enjoyed this post! The type of socks will depend on the shaft height of your boots. But as long as they don’t show above your boots, you’re all set! 🙂 For ankle boots, either wear your regular ankle socks or try a taller sock like this: For knee-high boots, you can wear regular socks or taller socks like these: Hope that helps! Let us know if you need other options. Thanks so much for reading! ~Team Busbee

  3. I love everything in this post! I really enjoy wearing dresses, and living in Massachusetts I have to have a way to keep warm. My favorite is the black midi with brown knee high boots. I have a cable knit sweater dress that fits the bill, and the outfit winds up being warm, comfy and chic. I appreciate your advice about boot height and hem length; that’s the only place it can get tricky!

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