Winter Dress Shoes

Tuesday, December 27th 2022. | Weddings

Winter Dress Shoes – If you love to wear dresses all year round, even during the winter months, good news, this post is for you!

Pack those summer dresses and say goodbye to those summer shoes because here are the best types of shoes to go with dresses on cold winter days.

Winter Dress Shoes

Winter Dress Shoes

When putting together your winter wardrobe, you want to make sure you have the right shoes that are not only functional for cold weather, but also stylish.

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I like to pair my outfit with cozy layers like a trench coat or a black leather jacket in the winter months, but the boots really complete the look in my mind. Here are my favorite boots to go with winter dresses and my tips for styling them in the cold weather!

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When looking for the right type of colder weather boots, there are tips and tricks I like to follow to keep them fashionable and functional.

Especially if you live in a winter climate where you deal with snow/ice, rubber soles on your winter boots are a must!

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Of course they’ll keep you safe thanks to the non-slip material, they’re also super durable and won’t get your shoes wet.

Sturdy boots with rubber soles are a good choice as I find them to be the most comfortable and practical for cold weather dressing.

In colder weather, we all want to do everything we can to stay as warm as possible. When it comes to styling dresses, especially mini dresses that are shorter, I like to compromise on the style of the mini dress and go for higher coverage shoes that are taller and cover more of my leg.

Winter Dress Shoes

Not only are they super stylish with above-the-knee or knee-length tops, but they also double as extra leg coverage to keep you warm.

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I like to double down on this tip and pair black tights with my tall boots for a cool weather and super cute look.

As a petite girl, I like to wear high heels when possible, but when it comes to the winter months, I prefer shorter heel styles.

When dealing with the winter elements, the lower heel height feels more comfortable and secure while still providing a slight lift that I like.

When it comes to winter heels for dresses, no matter what heel height you choose, my biggest tip is to go for block style heels versus narrow stilettos and strappy sandals.

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Block heels are generally more comfortable, durable and the best choice for winter dressing.

#1 Nude Chelsea Boots – I love the nude colors of these Chelsea boots and the chunky sole is very trendy and perfect for the winter season

#2 Chocolate Knee High Boots – These chocolate knee high boots are gorgeous! Combine with a knitted sweater dress or maxi skirt for an elegant winter look

Winter Dress Shoes

#3 Black Croc Combat Boots – The croc texture on these combat boots is a fun twist on the classic! Combine them with a floral mini dress or a white shirt dress and an oversized woolen coat

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#4 Ankle Boots in Ivory – Ivory boots are so chic for winter! Pair them with a monochromatic look for a very stylish winter outfit idea

#5 Black Patent Ballet Flats – These ballet flats get a fresh look with a patent finish. They look great in combination with clothes for work events or jogging

#6 Black Over The Knee Boots – I love these suede over the knee boots! They have a slight heel that flatters the feet and the rubber sole is winter weather approved

#7 White Sneakers – A good pair of white sneakers is a year-round must! I love the gold accent on this pair. Combine them with your favorite slip dress and an oversized trench coat

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#9 Block Heels – Block heels are so chic for winter and I love this gray suede for a transition to classic neutrals.

#10 Black Loafers – These loafers are trendy for Fall/Winter and come in so many great color options!

I love pairing higher boots like over the knee boots with a sheer dress on top! It’s the perfect combination with a shorter length dress and you can even style your sundress with taller boots like these to expand your wardrobe even more.

Winter Dress Shoes

It also looks great with tights and would be a great choice for a date.

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A great pair of thigh high boots is always what I’m most excited about styling for the winter months!

Knee high boots that actually reach the leg below the knee are very trendy right now. Over the knee boots are great with dresses of all lengths and offer leg coverage which is great for cooler weather.

Try knee-high boots in combination with midi dresses and mini dresses. They go great with sweater dresses that keep you warm when worn with tights!

Combat boots are my favorite flats to wear with dresses. When it comes to combat boots today, there are so many options (color, jewels, weaves, etc.)

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I love the rugged feel they offer to clothing and my favorite winter sports because they are stylish and functional.

Chelsea boots are really trendy right now and I love the edgy look they give to dresses.

This is a specific style of boot with an elastic edge and ankle height. If you want to pair your outfit with comfortable flats, chelsea boots are a fantastic choice.

Winter Dress Shoes

They look great with all kinds of dresses, be it a floral dress or a midi length sweater dress.

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If you’re looking for a stylish shoe option to go with your dress, cowboy boots are a fun option.

They are super comfortable, with lots of great flat/low heels that are as functional as they are fashionable.

Ankle boots are another of my favorite shoes to go with a variety of winter outfits. I love how comfortable they are and the block heels give me a bit of height.

Ankle boots are my go-to for dressing up every night and there are so many great styles that really go with everything!

Mid Heel Winter Shoes

If you have a pair of brown ankle boots, black ankle boots like I saw above, or white ankle boots, I think they look amazing paired with tights, a cute outfit and a nice cozy coat!

If you’re a flat person, ballet flats are a great choice for winter wear. They keep your leg mostly covered, keep you comfortable and add that feminine detail to any outfit that I just love.

Make sure you choose a ballet flat with a rubber sole that is suitable for the winter elements.

Winter Dress Shoes

If you’re anything like me, since becoming a mom, I love picking out sneakers more than ever! And with the right style, sneakers can look as casual or chic as you like.

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I love that they offer so much convenience, whether it’s playing with my girls or running from meetings/errands/car sales etc.

Sneakers are perfect for a winter outfit because they are functional and look very stylish when paired with a nice dress and your favorite winter coat on top.

Loafers and oxfords are really trendy right now! I love how they look with all outfits, but especially with dresses.

They add that casual cool element to any look and go great with all kinds of outfits. I love the look of a mini dress paired with higher socks and oxfords for a fun fashion look.

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Need a more elegant winter look? If so, heels are the right choice! While I tend to wear a lot of jeans and heels to keep my feet warm, I find that heels work great in the winter too.

Whether it’s a work event, a party, a winter wedding or a family vacation photoshoot, high heels combined with a dress are the perfect match that you can’t go wrong with.

When it comes to the winter months, I like to go for block heels and pumps with more coverage as opposed to the sandal style.

Winter Dress Shoes

Those of us on the shorter side won’t let the colder winter months stop us from wearing heels!

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Tiffany is the founder and editor of I am Style-ish, a Seattle-based fashion, motherhood, and lifestyle blog. Follow my daily adventures on instagram @tiffanyish and where I share daily Amazon deals at That doesn’t mean you can opt out of wearing a suit when you need to because it’s cold outside. It just means you’ll have to wear it more strategically, for starters

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