As temperatures finally drop, we’re ready to embrace fall fashion—and there’s no better season to refresh your shoe collection. With endless outfit possibilities, having the right selection of shoes on hand makes getting dressed effortless.
While boots are a fall staple, you’re not limited to them. There are plenty of stylish options to consider, so I’ve rounded up eight versatile, wearable shoes that pair beautifully with dresses and skirts. You might already have these in your closet, or you can pick some up through our recommendations.
When styling fall dresses, it’s important to think about more than just the shoes—you’ll want to consider the length and proportions of your outfit to create a balanced look.
For each shoe style I created an outfit, using items you’ve already have an introducing a few new finds for the season.
Let’s dive into the best shoe styles to wear with fall dresses (or skirts)!
8 Fall Shoes To Wear With Dresses

Tall Boots

Boots are probably the most obvious shoe option for the fall, and tall boots go great with midi and mini dresses.
They are versatile and, as long as you choose the right ones, surprisingly comfortable, which is why I consider them one of the best women’s boots for fall.
Above I’m using this popular Mango dress that looks like DVF but is only $79.99. It’s gorgeous. I swapped out the belt the dress comes with and went instead with this designer inspired one from Amazon for $19.99 and added this $30 bracelet to play off the hardware. Also from Mango is this best selling (in blog history!) crescent shaped bag for $50.
Our boot is the Kora Tall Boot from Nordstrom (I did a review last week here).
Available in black or brown for $170, in regular or wide calf.
I also like (and have) these knee-high leather boots from J.Crew , and if you’d like a suede option consider the Molly Knee High Boot from Sam Edelman .
You can see an example of how to style them with a classic grey dress in this post.
Ankle Boots / Booties

Ankle boots, or booties, are a great option in the fall to pair with dresses of any length but here I’m showing them with a mini dress.
I took the Shirred Mini Dress from Banana Republic Factory, added a pair of black tights and the Day Boot in ReKnit from Everlane.
For a budget friendly boot, consider this sock boot from Amazon’s The Drop. I have these and am very impressed with their comfort and quality. I bought them two years ago and they still look new despite frequent wear.
I’m 5’10 and too tall for this dress, but if you are shorter than me, this look is a lovely option, you an ankle boot as an alternative if a tall boot feels overwhelming for your frame.
I finished up the look with this reader favorite bag from Quince and these popular earrings from Mango.
Chelsea Boots

Technically, Chelsea boots fall under the category of ankle boots, but they deserve special attention. They were incredibly popular last season and remain a key staple in your fall wardrobe.
One of the most frequent questions I get is how to style them with dresses or skirts.
Many of you have this exact boot we feature last fall from Nordstrom. You can scoop it up now for $60 at Nordstrom Rack.
Because Chelsea boots have a heavier look, you can create contrast by pairing them with a flowy dress. In this example, I’ve chosen a dress in a seasonal color and pattern from Madewell, along with a coat that adds some weight, though the outfit works perfectly fine without it.
Heavy black boots can sometimes feel harsh against bare legs, but adding a wool sock the pops out at the top helps soften the transition and brings more visual interest.
To add even more depth, I’ve included this caramel quilted bag, which picks up on the color in the boot’s sole, tying everything together.
Pumps

Pumps are a classic, versatile closed-toe heel to wear with dresses in the fall.
They can be dressed up or down, and worn with maxi, midi or mini dresses to add a touch of elegance and sophistication.
You have so many options in this category. My favorite are the Marc Fisher Zala Block Heel. I have and wear these constantly, they are my go-to in black an neutral (above) suede.
I was thinking about holiday parities and found this beautiful fit and flare by Dress the Population at Nordstrom. I went with the tan suede too keep the look toned down but added some festive read rhinestone earrings.
For an under $100. basic, the Nine West Arlene Pointy Toe Pumps are nice, of course, you can spend as much as you want here, I’m just in a place where I spend more on sneakers and boots than heels.
White Sneakers

Pairing a dress with white sneakers is an effortless way to achieve a stylish yet casual look.
You don’t have to stick to sporty dresses either—low-profile white sneakers can complement everything from business-casual to relaxed, everyday dresses.
In this outfit, I went for a cozy, slouchy vibe by styling separates to mimic the look of a dress. Both the sweater and skirt are from Old Navy, creating a relaxed yet chic feel, perfectly paired with the Veja Esplar Bicolor Leather Low-Top Sneakers, which are fully stocked here. I wear these on repeat!
To complete the “cool girl” aesthetic, I added these SOJO sunglasses I snagged on Amazon during Prime Days, paired with bold door-knocker earrings for a statement touch. I finished the look with an oversized leather tote in a sophisticated neutral tone, pulling everything together perfectly.
Pointed Flats

Pointed-toe flats are a fall essential. They not only elongate the leg when paired with a dress or skirt but also add an effortlessly chic touch to any outfit. Personally, I love how a pointed flat elevates a classic pencil skirt, giving it a polished, sophisticated look.
I highly recommend adding at least one pair of pointed flats to your fall wardrobe in a versatile color—think black, navy, or a neutral that works for you.
I’m a big fan of “The Pointe” by Margaux; their shoes are worth every penny. But here, I’m featuring a velvet option I found on Amazon. At $130, they’re pricier than typical Amazon finds, but they’re perfect for the holidays and surprisingly comfortable.
To add some personality, I styled them with an animal print skirt, balanced by timeless neutrals like a staple gray sweater. I completed the look with a ladylike top-handle bag from Mango and classic earrings to strike the right balance between bold and understated.
Slingback Kitten Heels

For a dressier shoe to wear with fall dresses or skirts without the risk of towering in high heels, a slingback kitten heel is the perfect choice.
The lower heel provides comfort, while the slingback strap keeps your foot securely in place.
We’ve recently highlighted the French Sole Baton Heels, a chic block heel with timeless appeal, and the Nine West Rillas Pump, a pointed-toe option with a sleek, circular kitten heel.
Here, however, I opted for the Luna Leather Slingback Kitten Pump from Michael Kors, featuring a chic gold kitten heel that adds a subtle edge.
It’s the perfect match for this faux croc skirt, which I balanced with a long-sleeve cashmere polo, both from J.Crew. To finish the look, I added an affordable belt from Amazon and an elevated clutch from Fossil that has the look of a designer piece—polished and stylish!
Ballet Flats

Finally, one of the trickiest shoes to style with dresses and skirts is the ballet flat. You’ll want to be cautious with this choice because the wrong skirt shape or length can make the look feel frumpy rather than polished.
However, ballet flats are perfect when paired with a shorter skirt that gently flares away from the body.
For this look, I styled the popular tweed bow dress from Tuckernuck—a cozy yet incredibly polished piece that comes in a range of colors, including festive options like red and green for the holidays. It’s known for its comfort and versatility, making it a fall favorite.
I paired it with simple, well-crafted ballet flats from Margaux, and finished the look with a small structured bag and Amazon earrings that echo the dress’s buttons for a cohesive, elegant touch.
Tips On How To Match Shoes With Dresses
Consider Proportions
Proportions play a big role in putting together a stylish outfit. Balance is crucial.
The idea is to choose shoes that can hold their own with your outfit, not get lost in it.
You have to try things on and see how it feels. For example, you wouldn’t wear a pair of lugg boots with a chiffon occasion dress, but you could wear it with wool socks and a lightweight mini dress.
Choose Complementing Colors
I often choose neutral-colored shoes because they can be mixed and matched with just about anything in your wardrobe.
But if you want to wear a pop of color on your feet, try to stick with the same color family, or colors that complement each other on the color wheel.
For more on how to add color to your wardrobe, check out my post, How to Wear Color to Work (When All You Wear is Black).
Aim For Practicality
I tend to avoid extra-high heels simply because I find them to be impractical.
The same considerations can be made every time you decide which shoe to wear with your dress.
If you prioritize comfort and practicality, look for shoes that won’t be a pain to walk in, such as block heels or flats.
And be sure to consider what you’ll be doing, like if, for example, you’re going to be walking outside in the cold for an extended time versus spending most of the day in the office.
Don’t Be Afraid To Experiment
A lot of women forget that they can also experiment with footwear in different prints and colors.
Neutral-colored shoes are great for every day, but shoes in a fun print or a pop of color can instantly elevate any outfit.
What are your favorite shoes to wear with dresses in the fall?
I’d love to hear your thoughts on this. Do you prefer more classic styles or do you like to experiment with your shoes?
For more style tips and outfit inspiration, head over to the blog.
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