Category: how to style

Do you want to wear maxi dresses in the winter but are unsure what shoes to pair with them? I have got you covered with the ultimate styling guide of perfect shoes to wear with long dresses in the winter season!

Maxi dresses are great worn all year long as they can be worn for a casual day out or a special occasion no matter the season.

In the winter, you can pair them with cozy layers like a teddy coat or wool coat, but the shoes always complete the look.

I get so excited each winter season to pull out my boots and cold weather appropriate shoes!

They are my favorite accessory to style and truly are the perfect match to style with maxi dresses.

Here are the best shoes to pair with maxi dresses in winter and my top tips to styling them for cold weather!

3 Tips to Choosing the Right Shoes to Wear with a Maxi Dress in Winter

#1 Functionality: We all want to do what we can to stay as warm as possible when it comes to dressing in the winter.

So when it comes to styling a maxi dress in winter, I opt for closed toe shoes that fully cover my feet &/or are taller in shaft height to cover my leg also.

Even though you may not be able to see a full knee-high boot underneath a maxi dress, is gives an extra later of warmth underneath your maxi dress to keep you comfortable.

Look for a maxi dress that has a slit and pair it with over the knee or knee-high height boots. It looks so chic and is ultra functional for cold weather climates.

You also want to be mindful of the sole, and when it comes to winter the chunkier the better.

I also love the added height that chunky heels or platform height lends to a maxi dress outfit.

This creates long lean lines that we all want, and is great if you are dealing with any type of snow or ice.

#2 Heel Height/Shape: As a petite woman I love to wear any type of heel when I can, and I especially love it when wearing a maxi dress.

This helps to balance out the length of the dress and gives a more flattering look overall.

Whether it’s a short or tall heel height, just an inch gives a really flattering look when styling a maxi dress.

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.

It’s easy to opt for block heels or chunkier heels in general as it is more comfortable, more sturdy and is the best choice for winter dressing, as opposed to skinny stiletto heels and strappy sandals that are more fragile.

#3 Toe Shape: When it comes to styling a maxi dress, most of the time the majority of the shoe is hidden within the length of the dress, except for the toe.

They to pair a pointed toe shape with a maxi dress for a more dressed up feel.

This look is so chic and is great if you have a dinner party, work event, or any formal occasions in the winter but want to cover your legs.

If you choose a rounder toe shape, this works better for daytime/more casual style outfits!

Some ways to style this would be cute white sneakers with a knit style maxi dress, or nude Chelsea boots with a floral maxi dress.

The best shoes to wear with a maxi dress in winter:

Ankle Booties to wear with a maxi dress

Ankle boots such as pointed toe booties are one of my favorite shoes to pair with maxi dresses in the winter.

They are a perfect choice for day to night as the block heel is ultra comfortable but still lends some height.

There are so many great styles that truly go with everything, whether it be black leather ankle boots for a classic look or sparkly ankle boots for a holiday party.

Combat Boots that can be paired with a maxi dress

Combat boots are a great option to wear during winter as they have a very durable sole and they are ultra comfortable.

They are a great option to wear with maxi dresses as they give a bit of edge to contrast against the flowy fit of the maxi dress.

Combat boots are also really functional for all of the winter weather elements and come in a variety of styles to pair with all different kinds of maxi dresses too!

Cowboy Boots are a fun choice for maxi dresses

Another fun option to pair with maxi dresses is cowboy boots! The pointed toe and laid back slouchy fit is a perfect match for a flowy maxi dress, plus they are functional in colder climates as well.

A fun idea is to wear white cowboy boots with a white maxi dress and coat for a chic monochromatic winter look.

Tall Boots/Knee-High Boots the perfect choice for winter

Tall boots may be my favorite to pair with maxi dresses when I am looking for a bit of a dressier option!

It’s so chic when paired with a maxi dress that has a slit to show off the height of the boot.

Best thing is they keep your legs extra warm with the taller shaft height.

A good pair of thigh-high or knee-high boots is always what I am the most excited to style in the winter months.

Pair your knee-high boots with a long coat or trench coat and a knit maxi dress for a chic winter date night outfit.

Sneakers are so comfy and cute to pair with dresses

The ultimate comfort option for shoes to pair with maxi dresses? Sneakers!

I wear sneakers more than I ever did before since I have kids, and I absolutely love styling them with unexpected items like a maxi dress!

A white pair of sneakers is a great choice to pair with dresses in winter as they are functional and look so chic!

Just grab your go-to maxi dress and your favorite winter coat or leather jacket to layer on top. It’s a great way to get that effortless look.

Ballet Flats are a classic choice

Ballet flats are a good option to wear with maxi dresses in winter.

If you are not into heels or just looking for functional flat shoes option to wear all day, I would opt for a sleek pair of ballet flats!

They keep your foot mostly covered and offer a classic preppy/feminine detail to any outfit.

When it comes to styling a maxi dress with flats, just be sure to find a dress that won’t be dragging against the ground.

You can easily add a belt to a maxi dress and alter some of the length, or knot it up at the hem for a fun casual look.

*Expert Tip* Be sure to opt for a ballet flat with a rubber sole that is functional for all of the winter elements.

High Heels great especially for petite ladies

if you are like me and on shorter side, I am sure you can agree that we will not let the cooler months of the winter season deter us from wearing our heels!

If you are opting for a maxi dress for a winter event and need be more formal, heels are your best bet!

A good choice would be chunkier heels and fuller coverage pumps as opposed to sandal style, just to ensure the functionality of your outfit.

Maxi dresses are great for formal events as they look very chic but in my opinion they are way more comfortable than mini dresses.

Whether it be for a work event, a holiday party or a winter wedding, high heels paired with a maxi dress is a perfect match that you can’t go wrong with.

Loved this post? Don’t miss the below!

Are you looking for outfit inspiration on how to wear booties with skinny jeans? I’ve got you covered with the ultimate guide of outfit ideas and styling tips to make the most of this classic combo.

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As you can see, I love booties! The ones below are my go to for all of fall and winter. Living in the Pacific northwest, I definitely get use out of all my boots and ankle boots for the season.

We all have our favorite pair of skinny jeans and a pair of go-to booties in our closet. Skinny jeans are very fitted to your leg and waist, as opposed to mom jeans that are a looser fit or straight leg jeans that don’t hug your leg/ankle.

Pairing skinny jeans and booties together it is a classic combo that works for so many different occasions and is SO flattering. It is my favorite way to style skinny jeans for day with a cute pair of Chelsea boots or combat boots. Plus, the easiest way to amp it up for a night out look with a pair of ankle boots for a polished look.

There are style tips and tricks I’ve learned along the way that help when it comes to styling booties with skinny jeans.

Be sure to pin or bookmark this post for later when you are styling your next booties and skinny jeans look!

4 Tips to Styling Booties with Skinny Jeans

#1 Tuck It In:

To avoid any extra fabric at the top of the boot, I always suggest tucking in your jeans in the top of the bootie booties for an elongating effect for your leg. Since skinny jeans already are very fitted to the leg, they are super flattering to add body types!

Tucking the hem of the jeans into the top of the boot continues on that flattering line and is such a sleek look. I especially love to do this when I am pairing black on black, as I am petite and this really gives the illusion of longer legs.

#2 Opt for Cropped:

Of course the fit and length of your jeans depends on personal preference, but opting for a cropped length is a great option for pairing with booties as the hem of your jeans hits at the top of your boot as opposed to having to tuck it in.

#3 Be Mindful of Colors:

When styling booties with skinny jeans, try to be mindful of the colors you are wearing. The color pairing of your boots and denim combo is a simple way to differentiate day looks vs night looks in your wardrobe and match the occasion.

For instance, I would wear lighter colored denim and nude booties to style a casual look for day, and for a polished night look I would wear dark blue or black jeans with sleek black boots for a seamless look.

#4 Cuff It:

Whether you prefer a single cuff or double cuffed look, rolling up the hem of your jeans is a great option to control wear the jeans hit on your leg.

This is a great way to really customize the look of your jeans and is the best way to pair with booties as you can decide depending on the height of the bootie where you want your jeans to hit. This is a great tip to use for bootcut jeans as well.

You can try cuffing many types of jeans but skinny jeans work best since they fit so much closer to the leg. If you are petite like me, try a double cuff!

Try different colors of skinny jeans

You don’t have to just stick with black and blue jeans! Different colors, or even textures like these coated jeans are a good idea. These are the best option when you are looking for something to switch up your wardrobe.

What are the best booties to wear with skinny jeans

There are so many great options for booties, here are the best boots that you can shop:

Best Ankle Bootie for Petite Ladies

If you want something that is more flattering on the leg, I highly recommend these ankle cut booties. If you are petite like me (I’m 5’2″) with short legs so having the ankle cut out breaks up the line between the jean and the boot which helps elongate my legs.

These are a favorite as they have the chunky heel and the ankle cut out so they are super comfy and can be worn from fall to winter. I highly recommend getting some ankle

Below are the same booties from the photo at the top of this post and they are some of the best quality boots that I own. I have worn them so much but they still look new. They come in several colors and are perfect to wear with any outfit.

And as much as I love ankle boots – these outfits also work well with knee-high boots or over the knee boots too!

Related Post: Dresses to wear with Knee High boots

Booties with Skinny Jeans style guide

Here are a few ways that I’ve worn my booties with skinny jeans. These outfits work with many style of jeans but since most of us wear skinny jeans, that is what I’m focusing on!

Most of these are great ideas for the on-the-go woman who doesn’t have a lot of time to spend on her outfit but wants to look pulled together, especially during the colder months.

Chunky sweater with booties

Fall neutrals outfit

Related Post: How to Wear Flat Booties

Black Jeans + Nude Booties

If you are in need of an easy and flattering outfit – this is it! A cute black sweater (or swap for a black blouse, black bodysuit + blazer, etc.) and black denim paired with nude booties is a cute look for tons of occasions.

I would wear this in the fall for a lunch date or casual dinner out. You could also do this same look with a pair of black leather boots for an all black look that is super sleek.

Long Cardigan + Booties

In the fall, an easy outfit idea is to layer longer cardigans over tops and jeans. This adds an element of warm but also extends your wardrobe into multiple seasons.

This pairing is perfect with your favorite skinny denim and a cute pair of booties. There are so many different ways to recreate this look to make it your own!

Shacket + Skinny Jeans + Booties

We all love our cozy shackets in the cooler months! Pair your favorite shacket with a graphic tee, dark denim skinny jeans and black heeled booties for an effortlessly cool look.

This is an outfit I would wear in the Fall to drop my girls at school and head to work meetings! I love that it looks stylish and trendy without being too forced.

Try recreating this look with a sherpa jacket as well to mix it up! The options are endless here and you are guaranteed a chic look.

Graphic Tee + Blazer + Suede Booties

This outfit below is a great example of a single cuff on skinny denim. It looks so cute, raising the hem of the jeans just enough to showcase the gorgeous suede booties.

This is another fun way to style a graphic tee with your sneakers and booties, throw on a blazer and you are ready for wherever the day takes you.

Printed Blouse + Leather Booties

This outfit is so fun! Rock your favorite printed blouse (could be florals, stripes, leopard, you name it!) with an edgy black leather jacket and your go-to black skinny jeans and booties.

A leather jacket instantly gives a blouse a more sexy look and this is totally an outfit I would wear for date night.

More Skinny Jeans and Booties Style Inspiration

Here are a few more ways that you can style your skinny jeans with your boots for fall and winter.

Blazer + Classic Skinny Jeans + Heeled Booties

This outfit is so easy to recreate and it is comfortable, easy to wear and looks put together enough for work days/events.

This is a combination of all must-have wardrobe essentials in my mind: a good white tee, a black boyfriend blazer, skinny jeans and heeled booties.

You can mix up the colors here to fit your own personal style, or stick to the classics. Either way this look is a great way to pair booties with skinny jeans!

Neutral Trench Coat + Brown Booties

An oversized trench coat is the epitome of effortless chic and is trending for Fall 2022!

Pair your trench coat with a cute cropped knit, light blue ankle length denim and ankle booties for a gorgeous neutral outfit. I love the mix of textures here with the suede booties and knit sweater peaking out from under the trench coat.

This is a great outfit for a cold day and is ultra stylish.

All Neutral Everything

Are you a neutrals girl? If so, this is for you! This stunning outfit as seen below is on my list to recreate this Fall. I absolutely love all of the neutral tones and cozy textures paired together in this look.

You will need a great pair of white denim or off-white, nude booties, a good tan colored sweater and chic beige coat. This is a perfect look for Fall/Winter and it works for so many occasions.

Monochrome outfits are really easy to style as you just stick to a certain color family and don’t stray from it. You can recreate this with blacks, grays, browns, pinks, you name it!

This is such a fun way to wear booties with skinny jeans.

Pullover + Gray Skinny Jeans + Colored Heeled Booties

If you are a sweatshirt girl this is the look for you! Just pair your pullover sweatshirts with skinny jeans and booties!

You can wear classic brown or black booties or mix it up with a colorful bootie as seen below. I love the pop of color and think that would be so fun to add some extra personality to your look.

Oversized Scarf + Coat + Booties

Make the accessories the focus with an oversized cozy scarf and sleek leather booties. Such a great look for Fall and it would be so fun with a colorful scarf as well.

This is a great example of a cropped pair of skinny jeans as you can see just the top of her ankle before the booties. I absolutely love the look of the cropped denim as it really looks polished and put together.

Need more style inspiration? Don’t miss the below!

25 Jeans and Heels Outfits