21 Fall Shoes For Women And Outfits To Wear With Them

As the summer haze fades away, it’s time to trade in your sandals for a stylish pair of Fall shoes. The possibilities are endless – from sleek sneakers and stiletto heels to rugged boots and glamorous platforms. But let’s be real, not all shoes are created equal. The right pair can elevate an entire outfit from basic to breathtaking.

As I look forward to the season’s cozy vibes, rich colors, and luxurious fabrics, I’m excited to share my top picks for the best Fall shoes that will keep you warm and stylish.

What Shoes to Wear this Fall?

With fashion trends often reflecting society’s mood, footwear is a telling indicator of our collective sentiment towards getting dressed this season. A vast array of stylish and comfortable shoes have earned their place in our hearts – and wardrobes. Whether you’re on the hunt for a fresh pair of boots or simply curious to see which styles are making waves, our comprehensive guide will walk you through the must-have fall footwear essentials.

From rugged chunky boots and sleek loafers to sporty sneakers, there’s something for every taste. Take a peek at how we’ll be stepping into the new season.

Where to Buy Fall Shoes ?

As the seasons transition, our focus turns to finding the perfect pair of shoes to complement our fall fashion. Whether you’re a year-round high heel enthusiast or prefer to keep things casual with slip-ons, we’re here to guide you in your search for the ideal autumnal footwear. Boots and booties, in particular, are a staple of the season, offering a mix of practicality and style that’s hard to resist.

From Chelsea boots and knee-high riding styles to playful booties and pops of color, fall is an excellent time to invest in new shoes. To help you get started, we’ve compiled some top picks for the best Fall shoes at popular retailers like H&M, Dr. Martens, Zara, and Timberland.

21 – Black Never Goes Wrong

21 – Black Never Goes Wrong
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21 – Black Never Goes Wrong

Black ankle boots are a timeless favorite, offering a chic and versatile addition to any outfit. This modern take on the classic style features all the right details, making them perfect for everyday wear. Whether you’re dressing up or keeping it casual, these heeled ankle boots strike the ideal balance between sophistication and ease.

With their effortless styling capabilities and ability to complement every outfit, they’re a wardrobe staple that will have your back no matter what occasion arises. Pairing them with skinny jeans is an effortless way to create a stylish ensemble.

20 – Comfort First

20 – Comfort First
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If you’re seeking a harmonious blend of style and comfort, I’ve got the solution for you. The Chelsea Boots are an excellent choice to achieve this perfect balance. With their eye-catching quilted detailing and moderate heel, they can take you through every stage of your day in ease. These boots offer unparalleled versatility, making them an essential part of your everyday wardrobe. For added convenience, they feature a working zipper, ideal for the busy woman on-the-go. And the best part?

You can get these stylish Chelsea Boots for just $40.

19 – Ride or Die

19 – Ride or Die
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It’s no secret that we have a special affinity for boots – they evoke the cozy feelings of autumn, don’t they? Whether you’re seeking stylish long boots to share with your sister on a drizzly day or simply wanting to elevate your everyday look, I’ve got just the thing. Imagine pairing your favorite pair with a comfortable pair of jeans and a plush jacket… voilà! You’ll be all set for whatever the weather brings.

If you’re looking to make a statement, consider these eye-catching tall rain boots that are sure to turn heads – and can be yours for the reasonable price of $83.60.

18 – Doc Martens

18 – Doc Martens
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Are you tired of struggling to choose the perfect shoes to match your outfit? Look no further than Doc Martens! If you don’t already have a pair, you’re missing out on a versatile and stylish addition to your wardrobe. And if you’re unsure how to wear them with dresses, fear not – we’ve got some simple yet chic tips to get you started.

One of the easiest ways to style Doc Martens is to pair them with a summer dress.

Simply add a jacket or sweater for added layering and adjust according to the weather. For more inspiration, check out our roundup of top outfits featuring black Doc Martens perfect for girls on-the-go.

17 – Leopard Prints for the Win

17 – Leopard Prints for the Win
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Indulge in the majesty of leopard prints for a winning combination! Gaze upon this stunning piece of fashion art and let your imagination run wild. The ankle boots in leopard print are a must-have, and when paired with wash blue skinny jeans and a long black tunic top, create a simple yet effortlessly chic look that’s sure to turn heads.

16 – Sturdy Loafers

16 –  Sturdy Loafers
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The loafers’ versatility is unmatched, effortlessly elevating any outfit from casual to chic. When it comes to a comfortable yet stylish look, they’re the perfect choice. Their structured design makes them ideal for day-long wear, and they can instantly dress up even the most relaxed pieces in your wardrobe, such as sweatpants or distressed denim. For a simple yet put-together ensemble, pair them with your favorite jeans and a plain tee. The best part?

They’re as comfortable as a slipper and stylish enough to rival high heels. Our detailed guide on cute outfits to wear with loafers will ensure your feet are thanking you all season long.

15 – Charming Queen

15 – Charming Queen
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In times of uncertainty, a timeless solution presents itself: a pair of stylish over-the-knee boots. This autumn season serves as the perfect opportunity to treat yourself to a quality investment that will become a staple in your wardrobe, suitable for a wide range of occasions.

14 – Couple Goals

14 – Couple Goals
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If you want people to take notice of your impeccable style and wonder at how perfectly you and your partner complement each other, then achieving ‘couple goals’ status is within reach. One way to do this is by investing in a pair of iconic Chelsea boots that are sure to be a hit during the current season. And what’s more fun than twinning with your significant other?

13 – Sneaky Sneakers

13 – Sneaky Sneakers
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When it comes to dressing for fall, many of us tend to overlook one crucial aspect – our trusty summer sneakers. But why not? They can still be a great addition to your outfit even in the cooler months. In fact, they can add a fresh and stylish touch to any ensemble. Whether you’re heading out for a casual jog, a leisurely stroll, or even a night out on the town, these versatile kicks can elevate your look from bland to grand.

So don’t be afraid to break them out again – your fall wardrobe will thank you!

12 – Orange is the New Black

12 – Orange is the New Black
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Want to express your individuality through fashion? Look no further than a vibrant outfit that turns heads! When you want to make a style statement, try pairing a bright and playful pullover with bold Orange boots. The Orange hue stands out from the crowd because, let’s be honest, everyone’s already wearing the classic black options. This autumnal colour is perfect for adding a pop of personality to your wardrobe, so why not give it a try?

11 – Date Night

11 – Date Night
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The Roaring Twenties saw the rise of T-straps, affectionately known as ‘strap shoes’ back in the day. Not only are these heels incredibly comfortable, but they also exude a romantic charm that’s perfect for a date night look. Imagine pairing them with wide-leg pants, a crisp white shirt, and your go-to socks – it’s a timeless combination that never goes out of style.

10 – Outdoor Weekends

10 – Outdoor Weekends
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This weekend’s adventure in the great outdoors calls for an outfit that balances style with practicality. To stay cozy and prepared for any terrain, consider pairing a cropped tank top with a warm and fuzzy beanie. Add some comfort-friendly skinny jeans and rugged Timberland boots with a natural tan finish to complete the look. With this ensemble, you’ll be ready to take on whatever the weekend brings while still looking great.

9 – Cute and Chic

9 – Cute and Chic
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When it comes to replacing your trusty heeled booties, heeled mules are an excellent choice. They offer the perfect blend of weather-friendliness, thanks to their substantial material, and unexpected visual interest, courtesy of their open heel design. For a low-maintenance yet stylish outfit, team them with your favourite jeans and a cozy sweater.

Alternatively, they can serve as a versatile work shoe for fall, paired with heeled booties for added sophistication – be prepared to receive plenty of compliments.

8 – Smart Women’s Choice

8 – Smart Women’s Choice
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Similar in elegance to the ladylike shoes of the fall season, slingback flats and low heels possess a delicate charm that sets them apart from chunkier boots. Not only are they on-trend, but also surprisingly comfortable – making them an excellent choice for dressing up or keeping it casual. Whether you’re attending a formal event or just want to elevate your everyday look, these understated yet stylish shoes are sure to impress.

7 – Celebrity Style

7 – Celebrity Style

When it comes to styling accessories, celebrities often set the tone for what’s trending. Sheepskin Ugg boots are no exception – not only do they exude a chic aesthetic, but they’re also surprisingly practical for everyday use. It’s little wonder that A-listers adore wearing them on low-key days when they just want to keep things simple and comfortable.

If you’re a fan of celebrity fashion and looking to stay ahead of the curve, incorporating Ugg boots into your winter wardrobe could be a great way to go.

6 – Gossip Girl

6 – Gossip Girl

If you’re in the mood for something dressy, consider trading in your typical high heels for a Mary Jane pump instead. This style is closely linked to the fall season, evoking a sense of sophistication and maturity reminiscent of a grown-up schoolgirl uniform. The Mary Jane’s classic charm is inspired by none other than the stylish and iconic character Blair Waldorf from Gossip Girl, who embodies elegance and poise.

5 – Vintage style

5 – Vintage style
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As the seasons change, a nostalgic nod to 1980s British counterculture is once again taking center stage with the resurgence of heavy-soled lace-up boots this fall. This versatile silhouette can seamlessly transition from a slouchy suit to a flowery print day dress, effortlessly elevating your everyday look. Ditch your reliable loafers and swap them out for these chunky shoes to make a statement

4 – Too Cool to Care

4 – Too Cool to Care
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Slouchy boots have taken the fashion world by storm in recent years, and it’s easy to see why. Not only do they add a touch of edginess to any outfit, but they can also breathe new life into older pieces. Take skinnies, for example – while they may not be the most popular pant style at the moment, they can still be worn and styled in a way that’s both trendy and chic. Simply tuck them into your slouchy boots, add a cozy sweater or a stylish turtleneck, and you’re ready to take on the day.

The key is to balance the relaxed vibe of the boots with more structured pieces, creating a look that’s both laid-back and polished.

3 – Badass

3 – Badass
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Make a bold statement with these edgy yet feminine Kamari Black Buckle Boots. With their versatility and stylish design, they’re perfect for tackling any occasion that comes your way. At just $104.80, these Fall-style kicks are an absolute must-have purchase for the season.

2 – Cowboy

2 – Cowboy
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While cowboy boots have had their moment in the sun, we adore them as a textured element in a monochromatic ensemble. I know what you’re thinking – an investment piece that requires regular maintenance? But trust us, with proper care, these timeless treasures can be treasured for years to come. To get the most out of your pair, here are our top picks for styling cowboy shoes:

From there, it’s all about how you choose to wear them – and we’ve got some great ideas to share.

1 – Squad Goals

1 – Squad Goals
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As you search for the ideal Fall footwear for your group of friends, it’s essential to consider each individual’s unique style. Every woman within a close-knit group has her own distinct tastes, preferences, and fashion sensibilities. The key is to let these differences shine through in their collective look. By embracing their individuality, you can create a visually stunning and cohesive trend that reflects the personalities of each member.

I must admit, I’m thoroughly impressed by this particular squad’s ability to bring together their favorite trendy Fall shoes, showcasing them in a single, eye-catching frame. Boots, in particular, offer an incredible level of versatility, effortlessly pairing with a wide range of outfits while maintaining their stylish appeal.

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