Skip to Content

40+ On-Trend Tall Cowboy Boots Outfits for Fall Fashionistas

By: Author Grace

Posted on  - Last updated:

40+ On-Trend Tall Cowboy Boots Outfits for Fall Fashionistas

Tall cowboy boots have become a key part of fall fashion, blending timeless style with modern trends.

From versatile clothing combinations to standout footwear choices, this guide offers inspiration for incorporating cowboy boots into your everyday lifestyle.

Discover how to mix these Western-inspired boots with the latest fashion trends to create looks that are both stylish and practical for the fall season.

1. A floral wrap dress is given an edgy twist when paired with a black leather jacket. The tall brown cowboy boots ground the look, adding a rustic vibe while keeping it feminine.

This outfit is perfect for outdoor fall events or casual strolls. Add a simple necklace or a crossbody bag for a complete fall-ready look.

a woman wears brown cowboy boots, a dark red floral dress and a black leather jacket (2)

2. A lace dress creates a soft and romantic base, and when layered with a tan suede jacket, it brings warmth and texture to the outfit.

The tall cowboy boots enhance the Western flair, making this look great for a fall day at the pumpkin patch or outdoor gatherings.

Finish the look with a few bohemian-inspired accessories like a wide-brim hat or layered necklaces.

a woman wears a brown jacket, white lace dress and brown cowboy boots

3. For a casual, country-inspired look, a plaid button-down shirt paired with white denim shorts creates an effortlessly cool vibe.

The tall cowboy boots pull the outfit together, making it ideal for warmer fall days or casual weekends. The addition of a brown belt with a Western-style buckle adds extra detail to the ensemble.

a woman wears a blue plaid shirt, white shorts and brown cowboy boots

4. A floral romper with flowy sleeves is a fun and feminine choice for fall. Paired with cream-colored tights and tall brown cowboy boots, this look has a playful yet chic vibe.

This outfit is great for transitional weather and can be accessorized with a simple crossbody bag and delicate jewelry.

A woman wears a white floral mini dress, white sheer tights, and brown cowboy boots

5. A cozy knit sweater dress in a deep navy shade looks stylish when paired with lace tights. Tall cowboy boots in a warm brown shade add a rustic touch, making this outfit both comfy and chic.

Perfect for coffee dates or weekend outings, this look can be finished with minimal jewelry and a tote bag for a practical yet stylish addition.

A woman wears a navy blue sweater dress, white patterned tights, and brown cowboy boots

6. For a sleek and polished fall look, pair a turtleneck sweater dress with a long wool coat.

The tall cowboy boots in a rich brown tone add a touch of Western charm to this otherwise city-chic outfit.

This look is ideal for walking through town or meeting up with friends for brunch. A small leather bag or statement earrings would be perfect finishing touches.

a woman wears brown cowboy boots, a beige sweater dress, a cream trench coat

7. A cream lace mini dress paired with a tan suede jacket creates a romantic and boho-inspired look. The tall brown cowboy boots add a rugged touch, making this a perfect fall festival outfit.

The combination of delicate lace and tough suede creates balance in the outfit. A fringed bag or layered bracelets would complete this look beautifully.

a woman wears a white lace dress, a brown jacket and brown cowboy boots

8. A denim-on-denim look gets a Western upgrade when paired with tall cowboy boots.

Distressed jeans and a denim jacket create a casual and cool outfit, while the boots give the ensemble a country flair.

This look is perfect for a day at the ranch or a casual fall outing. Finish it off with a statement belt buckle for extra detail.

a woman wears a denim jacket, ripped jeans and brown cowboy boots (2)

9. A plaid button-down shirt is a fall staple, and when paired with black leggings and tall brown cowboy boots, it creates a simple yet stylish look.

Perfect for exploring the fall foliage or running errands, this outfit is cozy and versatile. A simple pendant necklace or a wool scarf would be great accessories to complete the look.

a woman wears a plaid shirt, dark jeans and brown cowboy boots (2)

10. For a more polished take on cowboy boots, try pairing them with a black blazer dress. This look combines modern city style with Western charm, making it perfect for a night out.

The tall cowboy boots add an unexpected twist to the chic blazer dress, creating a look that’s both bold and sophisticated. Minimal jewelry and a sleek clutch will elevate the outfit even more.

A woman wears a black blazer dress, with tall brown cowboy boots

11. Pairing a floral midi dress with a cozy mustard-colored cardigan creates a perfect fall look.

The tall brown cowboy boots add a rustic vibe, making this outfit ideal for autumn outings, like pumpkin picking or casual strolls.

The warm tones of the cardigan and the floral pattern blend seamlessly with the fall landscape, while the boots provide comfort and style.

a woman wears tall brown cowboy boots, a dark red floral dress and a mustard cardigan 2

Tall Black Cowboy Boots Outfits for Fall

Tall black cowboy boots are the perfect fall footwear, offering both style and comfort. They bring a touch of Western flair to your wardrobe while being versatile enough to match different looks.

1. A rust-colored, flowy midi dress is paired beautifully with tall black cowboy boots.

The dress has a tiered design, adding movement and texture to the look, while the black denim jacket gives it a bit of edge.

The subtle slit in the dress adds a modern twist, and the boots anchor the outfit with a rustic vibe. This is the perfect combination for a fall day out at a pumpkin patch or an evening stroll.

a woman wears a rust dress, black cowboy boots and a black denim jacket

2. For a city-chic look, try a plaid mini skirt with a turtleneck sweater, topped with a sleek black leather jacket.

The tall black cowboy boots elevate the outfit, adding a Western touch to an otherwise classic fall look.

A simple black crossbody bag would be the perfect accessory to complete this outfit. This is ideal for casual fall days where you want to stay stylish but comfortable.

a woman wears a beige turtleneck, a plaid skirt, black cowboy boots and a black leather jacket (3)

3. Nothing says cozy like a soft, fringed poncho paired with leather leggings and a white knit top.

The tall black cowboy boots make this outfit feel grounded and balanced, while the poncho adds a layer of warmth and style.

This look is ideal for casual fall festivals or outdoor markets. Add a felt wide-brim hat to give it even more autumn appeal.

a woman wears a plaid shawl, black leggings and black cowboy boots (2)

4. For a sleek, streamlined look, opt for a long black coat over black skinny jeans.

The tall black cowboy boots maintain the clean, elongated silhouette while offering comfort and style. A beige scarf adds warmth and contrast to the all-black look, perfect for crisp fall days.

a woman wears black cowboy boots, black pants and a black trench coat

5. A cozy, oversized cable-knit sweater dress pairs effortlessly with tall black cowboy boots.

The long, belted trench coat adds sophistication, and the deep V-neck of the sweater dress creates a flattering silhouette.

This combination works well for a chilly fall evening, where style and comfort are key.

a woman wears a white dress, black cowboy boots and a brown coat

6. Amp up the glamour with a dark faux fur coat layered over a fitted bodycon dress.

The tall black cowboy boots create an unexpected contrast, giving the outfit a unique blend of city chic and Western flair.

A black belt cinches the waist and pulls the look together. Perfect for a night out in the city.

a woman wears black cowboy boots, a dark dress and a black fur coat

7. A classic denim skirt and tall black cowboy boots make a timeless combo. Add a black leather coat for a cool, urban vibe.

This outfit balances casual with edgy, making it perfect for weekend outings. Keep accessories simple with a black handbag and subtle jewelry.

a woman wears a black leather coat, a black shirt and a black skirt and black cowboy boots

8. For a laid-back, country-inspired look, pair a red plaid shirt with ripped skinny jeans. The tall black cowboy boots complete this classic Western ensemble, making it perfect for casual outings.

The plaid shirt brings a pop of color, while the distressed jeans add some edge. Finish the look with a simple brown belt and minimal accessories.

a woman wears a red plaid shirt, ripped jeans and black cowboy boots

9. Nothing says fall like a cozy fringe poncho paired with black skinny pants. The tall black cowboy boots tie the outfit together with their Western charm.

This look is ideal for outdoor fall events or cozy weekends at home. A wide-brim hat or statement earrings would be great finishing touches.

a woman wears a plaid shawl, black leggings and black cowboy boots

10. Go for a mysterious and sleek look with an all-black ensemble. A long black coat, skinny jeans, and tall black cowboy boots create a cohesive, polished look.

Top it off with a black cowboy hat for extra Western flair. This outfit works great for cooler fall days and brings a sense of sophistication with its monochrome palette.

a woman wears a black trench coat, dark jeans and black cowboy boots

11. A plaid button-up shirt dress makes for a cozy and stylish fall outfit. Pairing it with tall black cowboy boots adds a touch of country charm.

The addition of a wide belt cinches the waist, adding structure and shape to the flowy dress.

Complete the look with a felt wide-brim hat for that perfect fall-in-the-woods vibe. This outfit is both casual and trendy, making it great for a relaxed day outdoors.

A woman wears black cowboy boots with plaid dress and a belt

12. For a bold and modern fall look, a bright yellow trench coat paired with black skinny jeans and tall black cowboy boots is perfect.

The trench coat’s belted waist gives the outfit a tailored silhouette, while the tall boots bring an unexpected Western flair to the vibrant coat.

Add a black wide-brim hat to bring it all together. This outfit is ideal for making a statement while staying warm and comfortable.

A woman wears a yellow trench coat, black blouse, black pants, black cowboy hat, with black cowboy boots

13. For a more polished city look, a long gray wool coat layered over a black sweater dress is an elegant fall ensemble.

The tall black cowboy boots add some edge, while the coat provides warmth and sophistication.

This look works well for both casual days and more formal settings. Large hoop earrings or silver statement earrings would elevate this outfit even further.

A woman wears a grey long coat, dress, with black cowboy boots

14. A checkered fur coat with a belted waist creates a structured and stylish look, perfect for colder days.

Paired with tall black cowboy boots and a black cowboy hat, this outfit brings a refined Western vibe to city streets.

The coat’s pattern adds visual interest while the boots balance the look with a modern touch. This outfit is perfect for wandering through the city or a cozy evening out.

A woman wears a gray long coat and black cowboy boots

15. A chunky, oversized pink sweater adds a pop of color to your fall wardrobe. Pairing it with dark wash skinny jeans and tall black cowboy boots creates a comfortable yet fashionable look.

The sweater’s loose fit contrasts perfectly with the slim jeans, and the boots add some edge.

This look is perfect for casual outings and can be accessorized with a simple crossbody bag or a bold necklace.

a woman wears a pink sweater, jeans and black cowboy boots

Tall White Cowboy Boots Outfits for Fall

Tall white cowboy boots are a refreshing and modern twist on classic Western footwear.

Their clean and crisp look makes them versatile for fall, allowing them to be styled in both casual and dressier outfits.

Let’s look at some great ways to wear tall white cowboy boots this season.

1. Pairing a chunky white sweater with light-wash denim shorts creates a relaxed yet stylish look.

The tall white cowboy boots add a Western vibe, while the simplicity of the outfit lets the boots stand out.

This look is perfect for warmer fall days or outdoor gatherings. You can complete the outfit with minimal accessories like stud earrings or a delicate necklace for a polished finish.

a woman wears white cowboy boots, a white sweater, denim shorts

2. For a more polished fall look, try a white sweater dress under a camel-colored trench coat.

The tall white cowboy boots elevate the neutral palette, adding a pop of brightness to the earthy tones of the coat.

This outfit strikes the perfect balance between cozy and chic, making it great for chilly fall afternoons. Finish the look with gold hoop earrings or a neutral tote bag.

a woman wears white cowboy boots, a white sweater dress, a trench coat

3. Plaid is a fall staple, and when paired with white jeans and white cowboy boots, it creates a clean, cohesive look.

This outfit is casual yet stylish, perfect for a day at a fall festival or a casual outdoor event.

A wide belt and subtle accessories like a silver bracelet can complete the look without overwhelming the simplicity of the outfit.

a woman wears white cowboy boots, a plad shirt and white pants

4. A soft, romantic lace dress looks stunning when layered under a long white coat. The tall white cowboy boots keep the outfit grounded while adding a bit of edge to the delicate lace.

This is a perfect look for fall photoshoots or seasonal gatherings. Add a wide-brim hat to bring even more charm to this elegant fall ensemble.

a woman wears white cowboy boots, a light pink dress and a white coat

5. A black turtleneck dress is a fall essential, and when paired with a gray plaid coat, it creates a sleek and stylish look.

The tall white cowboy boots add contrast, brightening up the outfit and making it perfect for fall city outings.

Simple accessories like a structured handbag or silver hoop earrings complete this look effortlessly.

a woman wears white cowboy boots, a black dress and a patterned coat

6. A bright pink sweater adds a fun and youthful vibe when paired with distressed jeans and tall white cowboy boots.

The pop of color contrasts nicely with the clean white boots, creating a playful yet put-together fall look. A casual crossbody bag or a simple scarf would be great accessories for this relaxed outfit.

a woman wears a pink sweater, ripped jeans and white cowboy boots

7. For a casual, outdoorsy vibe, style a floral mini dress with a classic denim jacket and tall white cowboy boots. This combination is perfect for country-inspired outings or casual fall festivals.

The boots give the floral dress a touch of Western charm, while the denim jacket keeps the look laid-back. A white cowboy hat would complete the country aesthetic perfectly.

a woman wears a denim jacket, floral dress and white cowboy boots

8. A cozy red sweater paired with dark denim shorts makes for a stylish fall look. The tall white cowboy boots contrast the bold red, creating a balanced outfit that feels casual yet cool.

This outfit is ideal for days when the weather is still mild, allowing you to enjoy the beauty of fall while staying comfortable.

a woman wears a red sweater, shorts with white cowboy boots

9. For a soft, bohemian fall look, wear a flowy floral dress with a lightweight knit sweater layered on top.

The tall white cowboy boots with embroidered details bring a touch of femininity to the outfit, making it great for relaxed fall weekends.

A pair of dangling earrings or a crossbody bag would be lovely accessories for this outfit.

A woman wears a knitted cardigan, a floral dress, and white embroidered cowboy boots

10. A flowy floral dress layered under a long tweed coat creates a charming fall outfit.

The tall white cowboy boots add a modern touch, making this look perfect for an outdoor concert or a casual event.

Keep accessories minimal, such as a small leather bag or a wide-brim hat, to maintain the outfit’s laid-back vibe.

A woman wears a long brown coat, a floral dress, and white cowboy boots

11. A cozy oversized sweater paired with a fringed scarf creates the ultimate cozy fall look.

The tall white cowboy boots add a touch of Western flair to the layered outfit, while the textured scarf gives the ensemble some extra dimension.

Perfect for brisk fall days, this outfit combines warmth and style effortlessly. A simple pair of hoop earrings or studded accessories can add subtle details to complete the look.

A woman wears a white fringed top, dress, knitted scarf, and white cowboy boots

12. A vibrant red sweater paired with a black pleated skirt creates a fun and fashionable outfit for fall. The tall white cowboy boots add a bold contrast to the dark skirt, making the look stand out.

This outfit is great for fall markets or casual outings, balancing cozy comfort with a chic vibe. Pair it with a small crossbody bag for a practical yet stylish accessory.

a woman wears a red sweater, a black pleated skirt, and white cowboy boots

13. Leather leggings paired with an oversized chunky gray sweater create a sleek, modern fall look.

The tall white cowboy boots add an element of surprise to the outfit, mixing Western and urban styles effortlessly.

Add a white cowboy hat to elevate this city-chic vibe. This outfit is perfect for city strolls or casual meetups with friends.

A woman wears white cowboy boots with leather leggings and a sweater

14. For a relaxed yet stylish fall outfit, pair a floral mini dress with a classic denim jacket. The tall white cowboy boots complete the look with a touch of Western charm.

This combination is perfect for weekend outings or casual fall events. Accessorize with a simple pendant necklace or a small leather bag for added detail.

a woman wears a floral red dress, a denim jacket and white cowboy boots

15. A light knit cardigan layered over a black turtleneck creates a classic fall look when paired with blue jeans and tall white cowboy boots.

This outfit is perfect for a cozy day at a café or a casual day of shopping. Add small silver jewelry or a tote bag to keep the look simple and comfortable.

The mix of neutral tones and white boots makes it versatile and easy to wear throughout the season.

a woman wears a sweater vest, a black turtleneck, ripped jeans and white cowboy boots