best fall shoes

Top 12 Must-Have Best Fall Shoes for the Season

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There can be a lot of debate about what the “best” is, but in this case, I’ll put it simply. The best fall shoes are the essential pieces that will get you through the season in style! Do you agree? Whether you’re looking for a timeless classic, a statement piece, or something in-between, there’s a shoe for everyone this fall. Keep reading to find the perfect pair(s) for you!

best fall shoes

1. Clogs

clog shoes fall outfit

If you haven’t added clogs to your fall wardrobe yet, now is the perfect time to do so. Though these shoes seem trendy, they’ve actually been around for a while, putting them under the “classic” category. Not only are they comfortable shoes, but they also add a touch of retro chic to any outfit.

Clogs are best styled for a more casual look, but a big bonus is that they’re versatile and can be paired with a variety of clothing options, from a cardigan and denim shorts to a floral midi dress.

2. Sneakers

white sneakers fall outfit

You’d be doing your shoe collection a disservice if you didn’t have a good white sneaker! Because when it comes to any season, sneakers are an absolute must-have in your wardrobe. Not only are they incredibly comfortable, but they also add a sporty and casual touch to your outfit.

Whether you’re running errands, traveling, or going for a casual weekend look, sneakers are the perfect choice. The right pair can effortlessly elevate your most casual outfit and add a cool and effortless vibe.

3. Mary Jane Flats

mary jane flats outfit

Mary Janes are characterized by their low heel, rounded toe, and iconic strap. And though a pair of Mary Janes may bring to mind visions of school uniforms for little girls for some people, when done right, they can look feminine and adult appropriate. The styling key? Pair them with other sophisticated and grown-up pieces in your wardrobe.

The best thing about these shoes is that they add a touch of femininity and elegance to any outfit, making them perfect for both casual and dressier occasions. For a casual look, pair your Mary Janes with a pair of straight jeans and a cozy sweater. Going for a dressier vibe? They look great with flowy midi skirts.

4. Mule Slide

mule slides fall outfit

Mule slides are the ultimate footwear choice for effortless style and comfort this fall season! These slip-on shoes are perfect for those who want a laid-back yet fashionable look. And with their open-back design, mule slides are a great transitional shoe for the changing weather. Whether you’re running errands or going out for a casual dinner, mule slides are the perfect finishing touch to any outfit.

One of the best things about mule slides is their versatility. Pair them with your favorite jeans and a cozy sweater for a casual and chic look, or wear them with a flowy dress for a more dressed-up vibe. The possibilities are endless!

Mule slides come in a lot of different styles, so you can easily find the perfect pair to match your personal style. Classic black leather ensures you’ll get a shoe you’ll wear over and over again, but it can also be a great time to add a statement – like an animal print. Invest in a high-quality pair of mule slides and you’ll have a go-to shoe that you can wear throughout the fall season and beyond.

Related: 8 Essential Ways To Effortlessly Transition Your Summer To Fall Outfits

5. Clog Heels

clogs fall outfit

If you’re looking for a fall shoe style that combines the elegance of heels with the comfort of clogs, then clogs heels are the perfect choice for you. These stylish shoes feature a chunky heel and a clog-style wooden sole, making them one of the current shoe trends but also one of the top classic styles at the same time. It’s a win-win!

In terms of style, opt for a neutral color like black or brown for the most timeless look. As a bonus, not only are heeled clogs stylish, but they are also pretty comfortable to wear. The chunky heel provides stability and support, while the clog-style sole adds a cushioning effect that makes walking a breeze. Whether you’re heading to the office or going out for a night on the town, these are a fashionable and practical choice!

6. Ankle Boots

ankle boots fall outfit

If you’re wondering what pair of shoes will never steer you wrong, here’s your answer: ankle boots. Ankle boots are a must-have style for fall, as they provide both style and functionality. Most importantly, these boots are versatile and can be worn with almost anything in your wardrobe, making them a staple in any fashion-conscious individual’s wardrobe.

One of the great things about ankle boots is their ability to transition seamlessly from day to night. Whether you’re going to work or meeting up with friends for dinner, ankle boots are the perfect choice.

Invest in a high-quality pair of ankle boots and you’ll have a go-to shoe that you can wear season after season. They’ll never go out of style. Even if you wore them last year, you can wear them again, and again, and again!

Related: Your Guide on How To Wear Ankle Boots (and More) With Jeans, Plus Tips for Always Getting It Right

7. Loafers

fall outfit with loafer

If you love timeless fashion, then leather loafers are a great buy. These easy-to-wear shoes are not only comfortable but they also add a touch of sophistication to any outfit. Whether you’re heading to the office or going out for a casual lunch date, loafers are the perfect choice.

One great thing about loafers is their versatility. Pair them with dress pants and a blazer for a polished and professional look, or wear them with jeans and a sweater for a more casual vibe. With their sleek and sophisticated design, loafers instantly elevate any outfit and add a touch of elegance.

Not only are loafers stylish, but they are also incredibly comfortable to wear. The slip-on style and low heels make them perfect for long days on your feet. You can confidently conquer your day in style and comfort with a pair of loafers on your feet!

8. Ballet Flats

ballet flats fall outfit

Ballet flats are such a classic and versatile style of shoe that I’d argue every woman should have a pair in her shoe collection! These timeless flats are not only comfortable, but they also add a touch of elegance and femininity to any outfit. (And are more grown up than Mary Janes.)

One of the best things about ballet flats is that they’re so easy to wear. Pair them with a tailored blazer for a polished and professional look, or wear them with jeans and a basic t-shirt for a more casual vibe. They effortlessly dress up your outfit without making it look too fancy.

9. Heel Mules

mules outfit

For special occasions, you may find that you need a dressier shoe option. Mules with a heel are a great option. These shoes feature an open-back design with height, combining the comfort of mules with the height and allure of heels. Mule heels are the perfect choice for those who want to elevate their outfits while maintaining a chic and effortless look.

Pair them with a flowy maxi dress for a fall wedding, or wear them with wide-leg denim for grabbing lunch. Find a heel height that works for you, but even the smallest block heel adds a little something-something!

10. Riding Boots

riding boots summer to fall outfit

Everything comes back around, right? Though I’d argue that something classic can’t really go out of style, for a while, the fall boot trend kept getting shorter and shorter, and now, taller boots are coming back.

Riding boots are a classic and versatile choice for fall footwear. With their tall shaft and equestrian-inspired design, riding boots add a touch of preppy sophistication to your outfit.

Pair them with jeans and a cable-knit sweater for a chic-meets-Ralph-Lauren look, or wear them with a dress and tights for a more polished and feminine vibe. Riding boots are especially great for those who want a bit of added height and coverage during the cooler fall months.

11. Knee High Boots

knee high boots fall outfit

These knee-high boots have a slightly more versatile look than riding/equestrian boots. The best thing about knee-high boots is their ability to elevate any outfit! Whether you’re wearing skinny jeans and a sweater or a dress and tights, knee-high boots instantly add a touch of sophistication and style. They are perfect for both casual and dressier occasions, allowing you to create endless outfit options.

In addition to their stylish appearance, knee-high boots also provide warmth and coverage during the cooler fall months. Their length helps to keep your legs protected from the elements while still looking fashionable. For a trendier touch, opt for knee-high lug sole boots this season.

12. Chelsea Boots

Chelsea boots outfit

If you like the style, Chelsea boots are a timeless and versatile style that could definitely be on your fall shoe wishlist. These ankle-high boots feature a classic design with elastic side panels, making them easy to slip on and off.

Another advantage of Chelsea boots is their comfort. With their low heel and cushioned sole, you can confidently wear them all day. Whether you’re running errands or shopping with friends, Chelsea boots will keep you looking stylish and feeling comfortable. You can get a pair with a chunky lug sole to add a trendy touch to your Chelsea boots.

How do you know if you should add a trend to your wardrobe? I created a resource for you that will help you build a wardrobe from scratch – including finding the right mix of trends and wardrobe staples!

Now, did you find the best fall shoes for you? Though I didn’t include cowboy boots in this roundup because they fit a very specific style aesthetic, if you like the look, then western-style boots can be your “something trendy” for the season.

Now that you’ve got the shoes, it’s time to make sure the rest of your wardrobe is fall-ready. Figure out how in the next post: Fall Wardrobe Checklist: These Items Just Scream “Fall”


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.