What Shoes To Wear With Maxi Dresses

What Shoes To Wear With Maxi Dresses


During the warm summer months I live in dresses, especially maxi dresses. I simply adore the long length, the classic style, the flowy silhouette, and the flattering feminine style which is ideal for every body type. One of the many great things about maxi dresses is just how versatile they are! They are perfect for nearly every occasion and can be dressed up or down with shoes and accessories. 

I purchased a black flowy maxi dress last year that I practically live in. I love that it has pockets, is cool and lightweight, is fully lined and is perfect for a backyard barbecue, date night, to run errands, wine tasting, wedding guest season, and that is just the beginning! And I tend to wear it with my slide sandals, wedges, and sneakers. Once the weather starts cooling down, it is a must with ankle boots, combat boots, and cowboy boots, especially this year since cowboy boots are such a hot trend.

If you’ve ever wondered what to wear with a maxi, I’ve got you covered! Today, I’m excited to share a roundup of the perfect shoes that will look great with your favorite (or new!) maxi dress.


What Shoes To Wear With Maxi Dresses

Flat Sandals

Flat sandals are a warm weather/summer shoe essential! They are perfect for nearly every casual event and look great with dresses, shorts, skirts, jeans, and more. I love wearing flat sandals with maxi dresses for an effortlessly chic look. For starters, my Dior Dway slide sandals are the most perfect shoes for summer! They are my favorite casual summer essential. I bought my first pair two years ago and another last year because I adore them.

They have a luxurious leather sole and insole, and the upper/top of the shoes are embroidered with the beautiful Christian Dior Paris logo. These sandals are available in a wide array of colors. I own them in black and in blue/white, which are very versatile colors and have the power to elevate any casual outfit!

I love wearing my slides with my maxi dresses throughout the year. They look great with solid colors, classic floral prints, nautical inspired stripes, and more.

Dior Day slide sandals

Tory Burch Flip Flops

I own a few different pairs of flip flops. But my Tory Burch Miller Sandals are my absolute favorite primarily because they are so comfortable! I purchased them in black patent leather in 2014, and they are still staples in my summertime wardrobe! I love the TB logo on the top, which is now considered a classic.

The sandals are made of leather and have a cushioned footbed, which makes them very comfortable. They fit true to size and come in a wide array of colors. These classic designer flip flops are only $198 (the same price I paid nearly a decade ago!), which makes them a great option.

I love wearing mine with dresses, especially with casual maxis. You can also pair them with a “dressier” long maxi dress that you would like to dress down and wear to a more casual event!

Tory Burch Flip Flops

Chunky Heels

Maxi dresses look phenomenal with chunky heels or block-heel sandals! I bought these Seychelles Manilla Heeled Sandals in brown in March and absolutely adore them. They are so comfortable! In fact, I love them so much that I ordered another pair in black! They are very affordable at under $120 with free delivery.

The block heel is made of wood and has a leather upper. They come in a few colors, and they also have a braided style, which is ideal for a beach vacation and summer in general. These beautiful chunky heel sandals are perfect for fall as well!

I love wearing mine with maxi dresses! I typically wear them with my black dress, but I can see wearing them with various colors and prints too! They are ideal for date night, wine tasting, a friend’s birthday, your birthday, an anniversary party, and more!

Seychelles Manilla Heeled Sandals

Loeffler Randall Penny Heel Sandals

High heels and heeled sandals are perfect for wedding guest season, date night, galas, and more! I am obsessed with my Loeffler Randall Penny Pleated Bow Sandals, which I bought a few years ago! I own them in a few colors, and leopard print is my favorite for fall. They pair wonderfully with any style maxi, especially in black.

This chunky heel sandal has a 3.5-inch heel, which is very comfortable, especially considering the height. I love everything about it, especially the signature knotted upper! Bows are a hot trend for 2023, but I have adored this style for years!

They look great with any outfit, especially a fabulous long maxi dress! They will elevate the most casual dress and are to a wedding, an anniversary party, a date night, or the office!

Loeffler Randall Penny Heel Sandals

Strappy Heel Sandals

Over the years, I have collected many high heel sandals, but my favorites will always be by Stuart Weitzman. They are classy, elegant, and are a celebrity, editor, and influencer favorite. They have the power to elevate any outfit!

I currently own these stunning Stuart Weitzman Nudistcurve 4” stiletto heel sandals in blush, and I just added them in black to my cart! They are made of leather (leather upper, sole, and lining) in Spain and are perfect. I adore everything about them, especially the thin strap across the top and the thin ankle strap, which allows you to adjust them to your liking.

They will look phenomenal with a classic solid color maxi dress, a lovely floral print, polka dot, stripes (or any print for that matter) in the style of your choice! This heeled sandal is ideal for date night, wedding season, a holiday party, or any event that requires you to dress up!

Stuart Weitzman Nudistcurve Ankle Strap Heel Sandals
Stuart Weitzman Nudistcurve Ankle Strap Heel Sandals

White Sneakers

Like many of you, I love my Golden Goose sneakers and wear them often. I own them in different styles, but my white sneakers are my most worn. These must-have Italian leather low-top sneakers have a signature star on the side and have been staples in my wardrobe for years!

They will look great with a lightweight casual long maxi dress in your favorite style and color (or print). They are a must for a casual backyard barbecue, lunch with friends, a baseball game, or a coffee date, and that is just the beginning!

Candie Anderson shares how to style white sneakers with maxi dresses Candie Anderson candieanderson

Golden Goose Studded Leather Slide Sneakers

My Golden Goose studded leather slide sneakers in black are one of my favorite purchases ever! I love everything about them; they make a statement and are ideal for summer, fall, winter, and spring. These Italian leather high-top sneakers have Goldens signature distressing and fit true to size. I’m obsessed with the studded trim, which is so fun!

I love pairing them with my black maxi dress. I also think they’ll look amazing with any color or print maxi (of your choice)!

Candie Anderson shares how to style Golden Goose black studded leather sneakers with maxi dresses

Combat Boots

According to Cosmopolitan magazine, combat boots are back and better than ever for fall 2023! They come in a wide array of styles and colors. I have had Chanel combat boots on my wish list for the last few years! Fashionphile has quite a few in a variety of styles available on their website now. With that being said summer is a great time to order a pair as they tend to sell out fairly quickly.

If you’re searching for a more budget-friendly pair, you can’t go wrong with the AllSaints Tori Lug Sole Combat Boots in black, which are a part of the Nordstrom Anniversary Sale right now. 

I love the chunky lug soles, which add a bit of height, and the “buckle strap across the vamp”. They have phenomenal reviews, with reviewers mentioning how comfortable they are!

These fabulous All Saints combat boots will look great with pants, skirts, and dresses this fall and winter. I can’t wait to pair them with a solid-color maxi dress or bold floral print! 

Ankle Boots

Now is a great time to stock up on ankle boots for fall. There are so many great sales happening, especially the Nordstrom Sale! Last year I purchased a pair of black Loeffler Randall Elise Slim Ankle Booties, which sadly aren’t on sale, but they are well worth the price.

I am such a big fan of the brand. Their shoes are well-made, comfortable, and gorgeous!

This pair of Loeffler Randall Elise Booties have a 3.5-inch block heel and side zip. These gorgeous ankle boots are easy to slip on and off, which I love! They look great with pants, denim jeans, and maxi dresses! Since they are slim, they will look great with a casual long maxi dress or a dressy floral print! They are a great option and will be staples in your wardrobe for years.

Loeffler Randall Elise Booties black ankle boots candie anderson candieanderson

Maxi Dress Outfit Ideas

Black Maxi Dress with Dior Flat Sandals
Candie Anderson shares what shoes to wear with maxi dresses including Dior Day flat slide sandals.

I love wearing my Dior flat slide sandals with casual maxis, especially my black maxi dress! My dress is currently out of stock, but this sleeveless maxi dress resembles it! Since these sandals make a statement, I only accessorized my maxi outfit with my trusty Van Cleef & Arpels necklace, which I adore.

This outfit will also look great with a denim jacket on a breezy summer night or if you’re going to the beach for the day.

Floral Maxi Dress with Flip Flops
Candie Anderson shares how to style flip flops and a maxi dress. What shoes to wear with maxi dresses.

How fabulous is this Free People Sundrenched Floral Smocked Bodice Maxi Sundress in blue? It is beautiful, and versatile and can be dressed up or down with flip flops, chunky heels, strappy-heel sandals, or white sneakers!

If you’re heading to the beach, invited to a barbecue, or heading to the city this summer, you’ll want comfortable shoes that will keep you cool. These classic Tory Burch Miller sandals will be the perfect types of shoes to pair with a maxi.

I styled this casual maxi dress with a denim jacket, flip flops, gold hoop earrings, and my Brixton Joanna hat, which is a hot trend and will keep you cool!

Casual Black Maxi Dress with Block Heel Sandals
black maxi dress with chunky heel sandals. What shoes to wear with maxi dresses

I hope my favorite smock maxi dress will be back in stock soon because it is so effortlessly chic! Thankfully there are quite a few similar dresses that are currently in stock, including this Free People Sundrenched Smocked Waist Tiered Cotton Maxi Dress that I absolutely adore! The thing I love the most about smock maxi dresses is they are classy, chic and will always be on trend! Not only that, they are incredibly flattering as well.

I styled my must have black maxi dress with my signature Seychelles Manila Heeled Sandals, and my Van Cleef & Arpels Sweet Alhambra Mother of Pearl Necklace for an effortlessly chic look. I would also pair it with a denim jacket on a cool summer night, which I am pleasantly looking forward to!

Black Maxi Dress with Loeffler Randall Penny Chunky Heels
What Shoes To Wear With Maxi Dresses

This versatile Vince Camuto Paneled Maxi Tank Dress in black will look phenomenal this summer and fall with the chic Loeffler Randall Penny chunky heels! You can pair it with a leather moto jacket on a cold summer night or for fall! This fabulous All Saints Dalby Leather Biker Jacket, which I styled it with is currently on sale, which rarely happens! When it comes to jewelry and accessories, I would wear a pair of gold hoop earrings and carry a black bag!

Floral Maxi Dress with Strappy Heel Sandals For Wedding Guests
Floral Maxi Dress with Strappy Heel Sandals For Wedding Guests

Lulus has gorgeous and budget-friendly maxi dresses for every occasion. Their gorgeous floral dresses for wedding guest season are a must! I love this beautiful Lulus Seasons of Love Blush Pink Floral Print Maxi Dress (in “blush pink floral print”). It is ideal for wedding guest season and will look phenomenal with a pair of strappy pair of heel sandals. I am partial to the beautiful Stuart Weitzman Nudistcurve Ankle Strap Sandals, which are well-made and wearable!

I styled this maxi dress outfit with my favorite faux pearl stud earrings, this bestselling Cult Gaia Eos Beaded Acrylic Box Clutch in pink (on sale), and a gold necklace!

Floral Maxi Dress with Block Heel Sandals
summer date night outfit with a floral print maxi dress, a denim jacket and casual shoes!

It is possible to create multiple “maxi dress outfits” with just one dress! For starters, If you’d like to dress this gorgeous floral print dress down, you can do so effortlessly with block-heel sandals and a denim jacket! My must-have Seychelles Manila Wedge Sandals are the perfect accessory! They are available in a few different colors, and are a great option since they are so affordable! The braided pair will look amazing with this dress, which gives it a beachy vibe. This outfit is ideal for a beach wedding, brunch, date night, or an evening with friends.

I styled this beautiful v-neck maxi dress for a summer date night. I paired it with block heels, a denim jacket, a gold necklace, and the pink clutch I featured above.

Casual Maxi Dress with White Sneakers
casual summer outfit with a blue maxi dress and white sneakers.

As someone petite, I know how difficult it can be to find maxi dresses that aren’t too long! This Loveappala Maxi dress is available in regular and petite sizes, and comes in five colors. During the summer, I love to wear varying shades of blue since it pairs well with denim and white sneakers! This classic casual maxi will look amazing dressed up with wedges or chunky heels, and dressed down with flat sandals or white sneakers!

I styled this dress with my favorite white Golden Goose sneakers, this Western-inspired Joe’s The Relaxed Denim Jacket in the shade “Dolores”, a trendy Chloe tote bag, and a gold necklace! It is the perfect outfit for dining al fresco, watching a golf tournament, a walk on the boardwalk, running errands, taking your dog for a walk, or just relaxing at home with a few friends.

Black Maxi Dress and High Top Sneakers
how to style a black maxi dress with high top shoes for a casual late summer or fall outfit

My love is strong for smock maxi dresses, and this cute Free People Sundrenched Smocked Waist Tiered Cotton Maxi Dress is a must! It will look great with these Golden Goose Studded Leather High Top Sneakers, which are absolute staples in my wardrobe! 

I styled this maxi dress outfit with my favorite Goldens, this classic Joe’s denim jacket, a quilted YSL camera bag, and silver hoop earrings. This is the perfect casual look for late summer and early fall!

Floral Print Maxi Dress and Combat Boots
fall outfit of the day with a floral print maxi dress and black combat boots.

What I love the most about this Loveappella Floral Print Sleeveless Jersey Maxi Dress is how wearable it is! I adore the beautiful bold floral print, which is ideal for fall. This gorgeous and affordable dress will look amazing with strappy heel sandals, white sneakers, pumps, slides, mules and combat boots!

With combat boots as popular as ever for fall 2023, I would style this black and red maxi dress with a black leather jacket, black combat boots, a gold necklace, and gold hoop earrings!

Floral Print Maxi Dress and Ankle Boots
Zimmermann maxi dress, ankle boots, Chanel handbag, diamond earrings and gold necklace

With fall just a few months away, now is a great time to start planning your autumn wardrobe! This gorgeous Zimmermann Devi Gathered Yoke Long Sleeve Chiffon Maxi Dress is luxurious and beautiful. It is sure to garner compliments every time you wear it. One of the many great things about this dress is that it is available in regular and petite sizes. This beauty will look phenomenal with pumps, wedges, heeled sandals, mules and ankle boots! I love my slim and feminine Loeffler Randall Elise ankle boots, which are available in a few different colors!

Since this dress makes a statement, I don’t feel that it needs many accessories. I styled this long sleeve maxi dress with Loeffler Randall ankle boots, diamond earrings, a timeless gold chain necklace, and a black handbag.

Discover even more summer and fall fashion essentials in the Candie Anderson Style Section: https://candieanderson.com/style

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Candie Anderson