If you like to wear dresses all year round, even including the winter months, good news, this post is for you!
Pack away that summer dress and say goodbye to those summer shoes, because here are the best types of shoes to wear with dresses during the cold days of winter.
When it comes to building your winter wardrobe, you want to make sure you have the right shoes that are not only functional for the cold weather but also stylish.
I love pairing my dresses in the winter months with cozy layers like a trench coat or black leather jacket, but the shoes really complete the look in my mind. Here are my top favorite shoes to pair with dresses in winter and my tips to styling them in the cold weather!
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3 Tips to Finding the Right Shoes to Wear with Dresses in Winter
When looking for the right type of shoes for cooler weather, there are tips and tricks I like to stick to in order to be fashionable and functional.
#1 Rubber Soles
Especially if you live in a winter climate where you deal with snow/ice, rubber soles on your winter shoes are a must!
Of course they help to keep you safe with the nonslip material, they are also super sturdy and will keep your shoes from getting wet.
Chunky boots with a rubber sole are a good choice, as I find them to be the most comfortable and the most practical when dressing for cold weather.
#2 Leg Coverage
With the colder weather, we all want to do what we can to stay as warm as possible. When it comes to styling dresses, particularly mini dress that are shorter in length, I like to compromise for the mini style dress and opt for higher coverage boots that are tall and cover more of my leg.
Not only is this so stylish with the over the knee or knee-high height, they also act as extra coverage for your legs to keep you warm.
I like to double up with this tip and pair black tights with my tall boots for a cold weather appropriate and super cute look.
#3 Heel Height/Shape
As a petite woman I love to opt for high heels when I can, but when it comes to winter months I gravitate towards shorter heeled styles.
When dealing with the winter elements, the lower heel height feels more comfortable and more safe, while still giving the slight lift that I love.
Another tip when it comes to heels is to be aware of the heel shape.
When it comes to heels in the winter with dresses, no matter the heel height that you opt for, my biggest tip is to opt for block style heels as opposed to skinny stiletto heels and strappy sandals.
The block heel in general is more comfortable, more sturdy and is the best choice for winter dressing.
10 Shoes to Wear with Dresses in Winter In Stock Now!
#1 Nude Chelsea Boots – I love the nude color of these Chelsea boots and the chunky sole is so trendy and perfect for winter weather
#2 Chocolate Knee-high Boots – These chocolate color knee-high boots are so gorgeous! Pair with a knit sweater dress or maxi skirt for a chic winter look
#3 Black Croc Combat Boots – The croc texture on these combat boots is a fun switch up from the classic! Pair these with a floral mini dress or crips white shirt dress and a oversized wool coat
#4 Ivory Ankle Booties – Ivory booties are so chic for winter! Pair them with a monochromatic look for an ultra stylish winter outfit idea
#5 Black Patent Ballet Flats – These ballet flats get a fresh take with a patent leather finish. These would look great paired with dresses for work events or running errands
#6 Black Over the Knee Boots – I love these suede over the knee boots! They have a slight heel which makes them ultra flattering on the leg and the rubber sole is winter weather approved
#7 White Sneakers – A good pair of white sneakers is a must year round! I love the gold accent on this pair. Pair these with your favorite slip dress and an oversized trench coat
#8 Black Cowboy Boots – These cowboy boots are so fun and I love the calf height!
#9 Block Heels – Block heels are so chic for winter and I love this grey suede color for a switch up to the classic neutral shades.
#10 Black Loafers – These loafers and trending for Fall/Winter and come in a bunch of great color options!
Related Post: The best shoes to wear with maxi skirts
The Best Shoes to Wear with Dresses in Winter
Tall Boots
I love pairing a taller boot like over the knee boots with a dress as seen above! It’s the perfect combination with the shorter length of the dress, and you can even style your summer dresses with taller boots like this to extend your wardrobe further.
This is such a cute look paired with tights also, and would be great option for date night.
A good pair of thigh-high boots is always what I am the most excited to style for the winter months!
Knee-high boots
Knee high boots that really hit the leg just below the knee are ultra trendy right now. Knee-high boots work great for dresses of all lengths and offer that leg coverage that is so great for colder weather.
Try knee-high boots paired with midi dresses and mini dresses. They also pair really well with sweater dresses which when worn with tights, can keep you pretty warm!
Related post: 15+ Dresses to wear with knee-high boots
Combat Boots
Combat boots are my favorite flat boots to wear with dresses. There are so many options when it comes to combat boots today (colored, bejeweled, woven, etc.)
I love the edgy feel they offer to dresses and are my go-to in the winter as they are just as stylish as they are functional.
Chelsea Boots
Chelsea boots are really trending right now and I love the edgy look they offer to a dress.
They are a specific style of boots with an elastic sides and ankle height shaft. If you are looking to pair your dress with a comfortable pair of boots that are flat, chelsea boots are an amazing option.
They look great will all kinds of dresses, whether it be a floral dress or a midi length sweater dress.
Cowboy Boots
If you are looking for a trendy option for shoes to wear with dresses, cowboy boots are a fun option.
They are ultra comfortable, with tons of great flat/low heeled options that are just as functional as they are fashionable.
Switch things up by pairing cowboy boots with a ruffled dress for a cute feminine feel.
Ankle booties
Ankle booties are another one of my favorite shoes to pair with different types of dresses in the winter. I love how comfortable they are and that the block heels give me a bit of height.
Ankle boots are my go to when I am dressing for day to night, and there are so many great styles that truly go with everything!
Whether you have a pair of brown ankle booties, black ankle boots like mine seen above, or white ankle boots I think they look amazing paired with tights, a cute dress and a great cozy coat!
Ballet flats
If you are a flats person, ballet flats are a great choice to wear with dresses in winter. They keep your foot mostly covered, keep you comfortable and add that feminine detail to any outfit that I just adore.
Be sure to opt for a ballet flat with a rubber sole that is functional for the winter elements.
White sneakers
If you are like me, since becoming a mom I tend to opt for sneakers more than ever before! Plus when styled correctly, sneakers can look as casual or as chic as you want.
I love that they offer so much comfort whether it be playing with my girls or running from meetings/errands/car pool etc.
A pair of sneakers is the perfect match for dresses in winter as they are functional and look so chic paired with a great dress and your favorite winter coat on top.
Loafers
Loafers and oxford shoes are really trending right now! I love the look of them with all outfits, but especially with a dress.
They give that effortlessly cool element to any look, and really work well with dresses of all kinds. I love the look of a mini dress paired with higher socks and oxfords for a fun fashionable look.
Pair with an oversized wool coat and you have nailed the it girl winter aesthetic.
High heels
Do you need a dressier winter look? If so, heels are the way to go! Even though I tend to wear a lot of jeans and heels to keep my legs warm, I find that dresses with heels work great in the winter as well.
Whether it be a work event, a party, a winter wedding or family holiday photos, high heels paired with a dress is a perfect match that you can’t go wrong with.
When it comes to winter months, I like to opt for block heels and fuller coverage pumps as opposed to sandal style.
Those of us on the shorter side are not going to let the cooler months of the winter season deter us from wearing our heels!
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