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Best Shoes to Wear with Dresses in Summer & Winter

Best Shoes to Wear with Dresses in Summer  & Winter

When you think about what shoes to wear with dresses, I'm sure a lot of shoe types and colors come to mind! If you're looking for summer shoes that go with dresses – especially sundresses – I'm sure you'll think sandals and sneakers.

And if you're curious which shoes to wear with dresses in winter, there are a variety of closed-toe boots and stylish weather friendly shoes that will work wonders for your dress outfit.

In fact, there are a lot of cute shoes to wear with dresses seasonally and even all year-round. So the options you can find will not limit your styling choice.

In today's post, I'm going to outline which sneakers, shoes, different types of heels and boots should be your top choices with dresses!

The list includes shoe types of all kinds to accommodate different dresses. Such as shoes with midi dresses, short and long dresses). I'll also talk about which shoes are the best for certain occasions and those that are most comfortable.

But most importantly, you will finish reading this post knowing exactly which footwear to wear with your dresses – all kinds of dresses – for summer, winter and transitional months.

You'll see that there are many great shoes to choose from!

Photos 1-3 by: Bruna Rico Photo

All the Best Shoes to Wear with Dresses

Best Shoes to Wear with Dresses in Summer

The Best Sneakers with Dresses

A summer dress with sneakers is never a bad idea. Actually, it's a wonderful idea for a casual look for the warmer to transitional seasons.

Sneakers, especially white sneakers are top casual choice of shoes to wear with sundresses!

And one can't deny that sneakers are some of the most comfortable shoes to wear with dresses, ever! Below are some of the best sneakers to wear with dresses:

White Sneakers with Dresses

Some of the best shoes to wear with dresses in the summer — but can also work year-round — are sneakers. Or aka in other parts of the world as tennis shoes.

White sneakers in particular always look fresh. You can choose a classic pair to a trendy pair. There are so many white sneaker styles to choose from!

Perfect for casual occasions such as a stroll in the park, attending a sports event or a laid-back date, white sneakers with your summer dress are a great choice.

Also, white sneakers are great with all kind of dress lengths, styles and colors. Sneakers are truly the shoes that go with dresses go-to!

However, the particular style of your white sneakers are going to be important for completing your sneakers and dress outfit. You can opt for the chunky style du jour, a classic sneaker or a trendy designer style.

If it works with your dress style, you can choose either a lower or platform sneaker. Looking for a more sporty look? Try a white high top sneaker or a more running shoe style.

You can complete your white sneakers and dress look with a caramel colored cross-body purse, a printed shopper or even a backpack that suits your style.

You can even add some statement earrings or hoops if you’re in the mood. If you're feeling it, anything goes with dresses and white sneakers, especially in summer!

Classic Canvas Sneakers

There are some great classic canvas sneakers in white and all colors in store. Some of my faves are Superga's Cotu or Old Skool Vans, which are affordable brand styles.

A pair of classic canvas sneakers are the perfect choice for casual summer outfits like cotton mini dresses or a linen maxi styles, to name a couple.

These kind of classic white canvas sneakers are definitely THE sneakers that go with everything, not just a dress! These make great breathable closed-toe summer shoes, if that's what you're after.

Shop White Canvas Sneakers:

White canvas lace up sneaker on white background.
TAOs Star Sneakers
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White canvas lace up sneaker on white background.
Superga Sneakers
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White canvas lace up sneaker on white background.
Keds Kickstart Sneakers
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Golden Goose Sneakers

I’ll admit, Golden Goose sneakers are not the most affordable sneakers, but they are a trend that seems to be lasting a few years now.

They offer so many styles from low to high tops, in a variety of finished and colors even. I have a white and silver pair myself that I wear with my dresses in summer and fall.

GG sneakers are classy, comfy and add a certain je-ne-sais-quoi to your dress. They are also a great sneaker to wear with skinny jeans, boyfriend jeans & much more.

Wearing Golden Goose sneakers with a short, neutral color dress such as white or black, will put a spotlight on your designer sneakers!

Shop Golden Goose Sneakers:

White and gold with star design lace up sneaker on white background.
Golden Goose Deluxe Superstar Sneakers
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White and Black suede and leather lace up sneaker on white background.
Golden Goose Superstar Sneakers
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White with silver star design lace up sneakers on white background.
Golden Goose Woman's Ball Star
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Leather Sneakers 

Leather sneakers never go out of style, especially with summer dresses, or any summer outfit, really! You can find them in solid colors such as black or white, prints and my favorite: gold or silver.

If you’re looking for a sign to dig your Nike Air Force sneakers out from the back of your closet, this is it. It’s time to revive your classic leather sneakers!

The best part? The more you wear them, the softer the leather gets. And they are extremely trendy right now too.

Gigi Hadid is a fan of mixing low-key leather sneakers with party-ready dresses for a night on the town. Suede sneakers are also a good choice. Just don’t wear them on a rainy day!

Shop White Leather Sneakers:

White leather lace up sneaker on white background.
TAOs Plim Soul Lux Sneakers
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White leather lace up sneaker on white background.
Esplar Leather Low-Top Sneakers
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White with decorative perforation embossing and silver heel tab lace up sneaker on white background.
Vintage Havana Reflex Sneakers
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Statement Sneakers

Make a statement in a pair of standout sneakers. There are so many to choose from. Bold patterns, animal prints, color blocking, raised outsole — you name it. Popular now? Those extra chunky sneakers.

For an interesting contrast, wear a pair of fancy bejeweled sneakers with a laid-back, casual dress in black or white.

Or try a pair of comfy dad sneakers with a posh, printed dress to create an eye-catching yet unexpected combo. Bonus points for wearing sneakers with a sequinned frock! 

Shop Statement Sneakers:

Brown cheetah print pattern lace up sneaker on white background.
Steve Madden Myles Sneakers
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Colourful blue red pink yellow design lace up chunky sneaker on white background.
Ray Tracer Apex Running Sneakers
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Metallic silver with black star design lace up sneaker now white background.
Golden Goose Hi Star Glitter Sneakers
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Knit Sneakers 

When it comes to knit sneakers, comfort is key. If you’re running errands across the city, this is the type of sneaker you want to choose.

Breathable and stylish and perfect for summer. Nike, New Balance, and Adidas are all stylish choices.

Try wearing them with stretchy dresses or even a cozy romper. Even skorts are making a comeback! On colder days, throw on a lightweight windbreaker. 

Lots of styles and colors of knit sneakers are available at Nordstrom!

Shop Knit Sneakers:

White knit lace up sneaker on white background.
Adidas Running Cloudfoam Pure 2.0
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Green knit lace up sneaker on white background.
Woolloomooloo Fraser Sneakers
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Black knit upper white sole lace up sneaker on white background.
On Cloud 5 Combo Sneakers
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Summer Sandals to Wear with Dresses

Sandals to wear with dresses you ask? Yes, please! From strappy to plain, thin heeled to no heeled, sandals are one of the most sought after shoes for summer dresses.

Many of the styles below are also excellent shoes to wear with skirts.

Lady wearing Brown sandals holding round purse with red summer dress.

Strappy Sandals

Whether minimal or ornate, strappy sandals never go out of style! From the nineties to now, they’ve been a staple in just about every woman’s summer rotation.

For work, a neutral sandal can look sophisticated with a blazer dress or a pleated midi.

Choose a high heel, a low heel a chunky heel or stiletto heels! I suggest strappy stiletto sandals to elevate your maxi dress for a fancier occasion summer, like a wedding.

I also find them one of the best shoes to wear with a jumpsuit to more formal functions.

Heading out on the town requires a bit more pizzazz. Try matching your metallic sandals to a metallic purse with either a neutral or brightly colored strapless dress.

Strap on your stringy sandals in either a high heeled, low heeled or flat version.

Shop Strappy Stilettos:

Black leather square toe adjustable ankle buckle closure sandal heels on white background.
Stuart Weitzman NudistCurve
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Beige patent leather strappy stiletto sandals on white background.
Calvin Klein Tegin Sandals
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Gold strappy stiletto sandals on a white background.
Stuart Weitzman Sandals
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Casual Sandals

Shoes to wear with dresses come in all shapes and sizes. And one fail-proof pair is any type of casual sandals.

From earthy Birkenstock outfits with dresses to sporty Teva and classic flip-flops, you’ll have these in your closet forever. Literally forever if you invest in a well-made pair!

With casual sandals, it’s easier to get away with being bolder on top. Why not try a ruffled sundress or a mini with a smocked bodice?

Sporty sandals for short dresses are perfect for summer. Tone down a fancier dress outfit with casual sandals and a neutral leather bag.

Neutral Slides

What shoes to wear with dresses that all the stylish summer gals are wearing? That's right: it's slides! Besides being very on-trend, slides are super comfortable shoes to wear with dresses.

And frankly, they are likely the best shoes to wear with summer dresses to keep things casual. Simple leather styles can add class to any sundress, denim dress or stretchy maxi.

On the other hand, puffy platform slides will add a touch of trendiness. (And nostalgia—does anyone remember The Spice Girls’s penchant for platforms?).

Slides can look great with a sportier tennis-style dress or even a long ribbed tunic. And don't forget: if you are wearing a simple dress, you can opt for less neutral & more funky slides to pair with your dress!

Shop Sleek Leather Slides:

Tan open square toe heeled slip on sandals on white background.
42 GOLD Lilith Slides
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Gold leather strap open toe slip on sandal on white background.
Steve Madden Greece Slides
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Brown leather open toe slide sandals on white background.
Madewelll The Boardwalk Post Slides
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Clear Heels

Clear Heel with dresses are transparent shoes that will add a touch of subtle edge and trend to any dress.

From a bodycon to a summer dress to a sequin number, almost all dresses will look incredible with a pair of clear heels!

Check out my post on how to wear clear heels with various dress types and more!

Shop Clear Heels for Women:

Steve Madden Clearer Sandals
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Clear PVC strappy mules with clear heels on white background.
Tony Bianco Sabelle Sandal
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Chinese Laundry Slides
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Espadrilles

Collage of 5 women wearing espadrilles with dresses.

Other great shoes to wear in summer with your pretty dress – and are also closed-toed – are Espadrilles. These always remind me of vacation.

Whether you choose a flat or wedge version, your feet will be ready to hit the streets of Greece. Or anywhere in between!

A decidedly summer style, espadrilles are one of the best shoes to wear with dresses. I love a long, flowy cotton dress or a tiered linen style. Try keeping things neutral with a white dress, beige espadrilles and a rattan bag.

A dress with a bit of flounce can look amazing with espadrilles too! Many brands make espadrilles these days.

But if you want to go with the top espadrilles makers, opt for Cantañer or Soludos! For more info, have a look at my post all about how to wear espadrilles.

Shop Espadrilles:

Tan leather open toe espadrille wedge heels on white background.
Stuart Weitzman Espadrille Wedge
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Black lace up round toe espadrille wedge heels on white background.
CASTANER Chiara Wedge Espadrille
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Platinum closed toe ankle wrap espadrille mid wedge heel on white background.
Jack Rogers Palmer Espadrille Mid Wedge
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Flirty Flats

Looking for cute shoes to wear with dresses? Flirty flats hit the mark every time.

There are endless types of flats to choose from. Versatile and comfy, this type of shoe can easily be worn across multiple seasons.

If you’re taller than average and not comfortable in heels, flats can be an effortless solution. Go for colorful flats for a pop of vibrance.

Or if neutral hues are more your taste, pair them with timeless wrap dresses.

Mules

Mules are one type of shoes that go with dresses all year round. For summer, choose a chic open toe style.

In the winter, it’s easy to pair a closed toe mule with an ankle-skimming dress. As for outfit options, they’re never ending.

Working lunch? Choose a white calf-length shirt dress and beige leather mules. Cocktails with your friends?

A belted mini and patterned mules will do the trick. Clasp an anklet around your ankle for a bit of sparkle.

Shop Mules & Slides:

Black open toe block heels on white background.
Vince Quinn Heels
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Off white leather slide heels on white background.
Rockport Farrah Slide
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Taupe faux leather pointed toe front buckle detail pump on white background.
Journee Collection Vianna Pump
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Clogs

Collage of 4 women wearing different dresses with clogs outfits.

Fashionable and classic clogs are great shoes to wear with dresses in a slew of cute styles. From mini to maxi and everything in between, a clog will give a dose of laid-back retro casual vibes to your dress.

I even like them with sweater dresses and socks for a cozy feel during cooler months.

And this season, you'll be able to find clogs in lighter materials, new colors, and even with heels! In fact, faux fur clogs are becoming increasingly most popular, so keep that in mind when planning your next fall clogs outfit with dresses.

Check out my post on all the style details on how to wear clogs with dresses & your favorite outfits!

Shop Clogs for Women:

Swedish Hasbeens Swedish Husband
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Bernardo Sky Sherpa-Lined Clogs
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Ankle Boots with Dresses

Ankle boots are cute shoes to wear with dresses throughout any season. There are so many styles to choose from! With ankle boots, there really is something for everyone.

And every occasion. Shopping with your friends, a family dinner, a first date or even a business meeting.

For all of these outfits, ankle boots are the way to go! They’ll pair well with summer dresses of all varieties.

There are a few ankle boots styles that are best for summer. White, beige, perforated, cut-out, and cowboy styles in particular.

Complete your summery outfit with a clutch, tote or duffel-style carry-all. Your go-to black leather bag is always a safe option as well.

And don’t forget the accessories! Simple hoop earrings are a must, as well as thin chain necklaces. Learn how to wear ankle boots with dresses of all types in my dedicated post!

White Ankle Boots

Say hello to the modern go-go boot! Since white is a neutral, these boots will go with everything.  I like wearing shorter dresses with white boots so that they can really be seen.

Try a dress with a knee- or mid-thigh hem. White ankle boots really are a blank slate. For a fashionable brunch, wear your white boots with a printed blue or purple dress. Complete the look with a white purse.

Shop White Ankle Boots:

White pointed toe ankle boot on white background.
Marc Fisher LTD Ulani Boot
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White pointed toe ankle boot on white background.
Steve Madden Elysia Bootie
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White square toe brown wooden sole ankle boot on white background.
ALOHAS West Ankle Boot
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Beige Ankle Boots

When you want your outfit to steal attention, choose beige ankle boots. Their natural hue will let your accessories and clothing do the talking.

For a chromatic look, wear head-to-toe neutrals in different shades of beige. A cable-knit dress looks right at home with beige ankle boots made of smooth suede.

Perforated Boots

Switch up your classic boots for a pair of perforated ones. Many of my favorite styles are made from ultra-soft, slouchy suede that’s as comfy as it is stylish!

A loose linen maxi dress or a simple wrap dress that ties around the waist will look great. Throw an oversized boho bag over your shoulder and you’re good to race out the door. This look would make Alexis Rose proud 😉

Cut Out Boots

Getting fancy? Try cut-out ankle boots. You’ll take your outfit to the next level and look fabulous! Especially in the summer, these boots will help your feet breathe a little easier.

Matching a cut-out dress with your boots can be an interesting look for meeting friends or running errands. At night, try a simple slip dress and a worn-in leather jacket. 

Shop Classic Ankle Boots for Women:

Sam Edelman Ulissa Boots
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Dolce Vita Spade Boots
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Sam Edelman Fawn Booties
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Cowboy Boots

Collage of 5 women wearing different cowboy boots outfits with dresses.

Cowboy boots – or western inspired boots – have made a big comeback in the last couple of years. In particular for summertime use! Kendall Jenner has been spotted many times wearing cowboy boots with a bikini by the pool.

Just throw a crochet dress on top and you’re good to go! These boots will also look great with a denim mini or plaid shirt dress and a canvas tote when running errands. You can choose an ankle or higher version to complete your outfit.

Need more info? See my newest post on the best dresses to wear cowboy boots with for over 20 amazing dress styles!

Shop Cowboy Boots for Women:

Dolce Vita Landen Boots
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Corral Boots A4047
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Roper Tall Stuff Cowgirl Boots
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Best Shoes to Wear with Dresses in Winter

Nine West Over the Knee Boots
Photo by Leo Shen

What shoes to wear with dresses in winter, you ask? There are so many great shoes, from loafers to high boots that you can choose from for the cooler months of the year.

From stylish to casual, there's a shoe for the dress you want and the occasion you're wearing it to!

Pumps

Pumps will always be classic. They’re timeless! Right now they're fashionable with a pointy front and stiletto or block heel. They are the shoes that go with dresses all the time and for any occasion.

For the office, try your pumps with a sheath dress with a simple slit and a pair of black patent pumps.

Pumps look fantastic with midi dresses all year round, really. Optional: sheer tights -unless the winter months near you are especially grueling!

A calf-length turtleneck dress keeps you warm and fashion-forward in the winter — especially when paired with a pair of bold pumps.

You can play with solid colors or patterns such as leopard prints. When running errands, loop a supple leather tote bag over your shoulder.

Worth mentioning that pumps are also appropriate shoes for summer dresses, if you need a closed-toe option.

Shop Women's Pumps:

Sam Edelman Hazel Pumps
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Steve Madden Block Heel Pumps
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Journee Cut-out Kitten Heel
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Loafers

Collage of 5 women wearing loafers with dresses.

Loafers are essential for on-the-go days. Not only are they comfortable, they’re polished and forever part of the current trends.

Great shoe type for work and play, with so many loafers, like classic penny loafers and slipper loafers to choose from!

Often, you can find loafers with unique buckle details or tassels. A midi or mini length dress is perfect for showing off your loafers and a pair of cozy socks.

Try a polka dot dress with a pair of sleek black loafers. Give your outfit a professional touch by adding a blazer. For low-key occasions, choose a denim or biker jacket. 

Learn how to style loafers with many outfits, including all types of dresses, in my dedicated post!

Shop Loafers for Women :

Sam Edelman Horsebit Loafer
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Agathea Chunky Loafer
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Oxfords

Although on the masculine side, brogues can be feminine if you want them to be. It all depends on how you style them.

A crisp shirt dress looks perfect with a pair of beige brogues, but you can add a little fun with a metallic or spotted print too!

Or a structured printed dress fits well with black and white brogues. Go for a school girl vibe with a plaid or pleated dress, tights and black brogues. A long wool coat will complete your outfit.

Shop Oxfords:

Black leather lace up oxfords on white background.
Vagabond Shoemakers Kenova Leather Derby
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White leather lace up oxfords on white background.
Cole Haan Original Grand Wing Oxford
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Black lace up almond toe oxfords on white background.
Josef Seibel Sienna 85
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Ankle Boots

The perfect shoes for winter are boots! And of all the best boots to wear with dresses, ankle boots are the most versatile. Below are my top faves for fall/winter.

Black or Brown Ankle Boots

Black and brown are two shades that never look out of place in a winter wardrobe. Or any wardrobe for that matter! Of course, you can choose a clean and simple black or brown boot.

However, if you want to switch it up, look for a pair with multiple buckles or metallic hardware. I love dresses that show off the shoe — even if it’s just a peek!

Try a paisley patterned flowy maxi dress with brown boots. At the beginning of the winter season, you can get away with a denim jacket on casual outings. For colder days, zip up a stylish puffer.

Shop Brown Ankle Boots:

Brown leather ankle boot on white background.
Nine West Cale 9X9
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Brown ankle boot on white background.
Dolce Vita Sirano
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Brown ankle boot on white background.
Sam Edelman Fawn
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Leather Ankle Boots

A quality pair of leather ankle boots are a must-have for winter dressing. Chances are, there won’t be many dresses in your wardrobe that wear badly with them.

Structured or slouchy, studded or plain, both silhouettes of ankle boots look great with mini, midi or maxi dresses.

That way, you can really show off your boots! For a coffee run, try crimson ankle boots with a red pleated midi dress and a toasty cropped shearling jacket on top.

Matching a cut-out dress with your boots can be an interesting look for meeting friends or running errands. At night, try a simple slip dress and a worn-in leather jacket. 

Shop Classic Ankle Boots for Women:

Sam Edelman Ulissa Boots
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Dolce Vita Spade Boots
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Sam Edelman Fawn Booties
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Combat Boots

Combat boots —Doc Martens in particular — have been a staple in alternative wardrobes for years. However, they’ve since become more mainstream. The new chunky styles from Steve Madden are pretty amazing too.

Model Kaia Gerber has been known to rock a pair of combat boots with feminine dresses and so has actress Julia Roberts.  Layer a blazer on top to add some extra warmth!

On a drizzly day, opt for a pair of waterproof combat boots. Elsa Hosk is also a fan of wearing a mini dress, tights and combat boots in the winter.

Take a peek at my post on how to wear combat boots with dresses of all kinds and more!

Shop Favorite Combat Boots for Women:

Black block heel combat boots on white background.
TAOS Crave Combat Boots
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White lug sole combat boots on white background.
Dr. Martens Platform Combat Boots
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Black lug sole combat boots on white background.
Dr. Martens Platform Combat Boots
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Chelsea Boots

Collage of 5 women wearing chelsea boots with dresses.

Chelsea boots are fab shoes to wear with dresses! They will give a rugged vibe to any dress, whether a maxi, mini, slip dress or sweater dress.

These boots, whether you choose them chunky or classic, are also insanely comfortable, which is an added bonus.

There are so many ways to wear Chelsea boots with dresses! Check out my post all about how to wear Chelsea boots for more!

Shop Chelsea Boots for Women:

Journee Collection Vista Bootie
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Sam Edelman Laguna Boot
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Blundstone High-Top Chelsea Boot
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Knee High Boots

If you’re wondering how to wear knee-high boots with dresses, I’ve got you covered. Or at least, your lower legs covered 😉

They are my favorite shoes to wear with dresses in winter because they keep my legs warm! Depending on how cold it is, you can choose a chunky knit dress that ends above your knees to show a little skin.

Too cold to bare anything? Pair your knee-high boots with a longer sweater dress or flowy winter florals dress. Layer a moto jacket and a fuzzy scarf on top and you're good to go. Anywhere!

Shop Knee Boots for Women:

Wally Tall Leather Boots
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FARYL by Farylrobin Terry Tall Boots
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Easy Spirit Chaza – Wide Calf Boots
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Tall Boots

Rihanna often favors boots so high that they cover her entire legs! Of course, your boots don’t have to get that high. From mid-calf to thigh height, all of these styles pair well with dresses.

A good way to get use of your summery dresses during colder months is to wear them with boots that end above the hemline.

Your legs stay warm and you look stylish! Take a cue from Hailey Bieber and sport thigh high camel suede boots with a beige sweater dress and tan overcoat.

Learn about all styling a sweater dress with boots in my latest post!

Shop Over-the-Knee Boots :

Stuart Weitzman Thigh High Boots
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Sam Edelman Ursula High Boots
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Calvin Klein Deedee Tall Boot
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Final Thoughts on Shoes to Wear with Dresses

Better equipped to know what shoes to wear with dresses? As you can see, the number of shoes to wear with dresses is many!

You really can't fail to style your dress during summer, winter and all the months in between with a fashionable or classic pair of shoes or boots.

The choice on how to style your dress with shoes really depends on where you're wearing your outfit, the look you're going for and the season. My biggest piece of advice is to have fun with it!

What are your favorite shoes to wear with dresses?

xo ShoeTease