Elevate your style game by pairing long boots with a variety of outfits. From workwear to wedding attire, these versatile shoes can be dressed up or down depending on the occasion. With their trendy appeal and versatility, it’s no wonder why long boots are a staple in many wardrobes. But if you’re feeling stuck in a fashion rut, we’ve got just the thing to get your creative juices flowing – today’s post highlights the most chic and stylish outfits to wear with long boots this season.
How to Wear Long Boots?
Types of Tall Boots
When it comes to knee-high boots, there’s a wide range of styles to choose from. Here are four common categories that cater to different tastes and occasions: Firstly, dressy tall boots make a statement with their sleek designs, often featuring leather or suede materials and a heel. They’re perfect for adding a touch of elegance to your look, whether you’re heading out for a night on the town or just want to elevate your everyday style.
Next, classic knee-high boots are timeless and versatile, typically coming in black or brown and made from leather or suede. They can be dressed up or down and paired with everything from jeans and skirts to dresses and leggings. Motorcycle tall boots take a more rugged approach, with thick soles and sturdy constructions that make them perfect for casual outings or outdoor activities.
Finally, riding boots are designed specifically for horseback riding, but they’re also super stylish and can be worn for various occasions.
With these categories in mind, here are some styling tips to keep in mind: avoid mixing light-colored boots with light-colored jeans; don’t pair boots with pants (it’s just not a good look); wear knee-length leather boots with short dresses for a chic combination; prefer darker shades of leather boots as they can match most outfits; and lastly, avoid pairing leather boots with long skirts, as it might not work out so well.
Now that we’ve covered the basics, let’s explore some stylish ways to wear long boots and take your shoe game to the next level.
41 – Black Long Boots Outfit for Work
Black attire is a timeless favorite among many. The versatility of knee-high boots in this color is particularly noteworthy. Not only do they complement black jeans effortlessly, but also blue jeans for a stylish contrast. These boots are ideal for various occasions – from parties to travel and everyday wear. Their adaptability makes them a valuable addition to any wardrobe.
40 – Brown knee-high boots
A versatile and practical choice among girls, ankle boots are a great match for many outfits. For those seeking a daily wear option, this style is an excellent investment. By choosing ankle boots, you’ll not only save money but also enjoy the convenience of being able to pair them with most colors in your wardrobe, eliminating the need for additional purchases.
39 – Tan Knee High Boots
If you’re looking to add some flair to your outfit without sacrificing style, consider pairing a stunning dress with tan knee-high boots. The light color of the boots is particularly appealing to many women, as it adds a touch of sophistication to any ensemble. Moreover, this versatile footwear can easily be paired with a white-colored dress for a casual yet elegant look that’s sure to turn heads.
38 – Black Riding Boots
If you’re a fan of black high-knee boots, then black riding boots are definitely worth considering. The versatility of these boots makes them an excellent addition to any winter wardrobe. They pair seamlessly with black jeans, blazers, sweaters, and other cold-weather staples. In fact, they can be worn with most of your winter outfits, making them a smart investment for your fashion budget. Plus, their understated design ensures you’ll feel comfortable and at ease when wearing them.
37 – Heeled Knee High Boots
Whether or not someone’s height matters little when it comes to wearing heels – if you enjoy the way they make you feel, there’s no reason not to indulge. What’s more, heels can be a chic addition to many winter ensembles. These leather boots, in particular, offer a range of designs and colors, allowing you to select the perfect pair to complement your outfits.
36 – Brown Knee High Boots Outfit for Fall
Looking for women’s knee-high boots? Look no further! These stylish options come in a range of colors and would pair perfectly with a mini skirt. What’s more, they’re designed for comfort, making them perfect for everyday wear. And the best part? They’ll complement long coats beautifully, making them an ideal choice for winter outfits.
35 – Black Over-the-Knee Boots
When considering a pair of professional boots, black over-the-knee boots are an excellent choice. Not only do they exude professionalism in any outfit, but they’re also incredibly versatile. You can wear them to work every day and pair them with a variety of attire options, such as sweaters and jeans for a chic, casual look or skirts for a more polished, feminine appearance.
34 – Patent Leather Over-the-Knee Boots
For those with a flair for the dramatic, the Patent Leather Over-the-Knee Boots offer an unparalleled level of sophistication and glamour. The glossy finish is sure to turn heads, making them a standout choice for anyone looking to add a touch of elegance to their outfit. Whether paired with a hoodie and t-shirt or dressed up for a night out on the town, these boots are sure to make a statement.
With their unique design and eye-catching appearance, they’re perfect for those who crave individuality and want to express themselves through fashion. The shiny finish gives off a party-like vibe, making them an ideal choice for special occasions. For anyone looking to elevate their style game and add some excitement to their wardrobe, these boots are definitely worth considering.
33 – Flat Over-the-Knee Boots
For those who prefer to steer clear of heels or simply don’t feel at ease in them, these boots offer a practical and comfortable alternative. Not only are they suitable for a quick stroll, but their understated design also makes them perfect for pairing with coats and skirts. With a focus on simplicity and comfort, this style is ideal for anyone who values ease of wear without sacrificing aesthetics.
32 – Moto-Inspired Over-the-Knee Boots
For those who prefer low-to-flat heels, this shoe option is an excellent choice. Its above-the-knee length makes it suitable for winter wear. Consider opting for grey or brown hues, as they are currently trending.
31 – Drawstring Over-the-Knee Boots
When it comes to pairing boots with outfits, people often forget about their versatility. Boots can be styled to perfection with a long coat and sweater combination. For instance, try pairing them with blue jeans and a dark-colored sweater for a chic look. If you’re on the hunt for party-perfect footwear that’s both comfortable and well-fitted, then these boots are definitely worth considering.
30 – Textured Over-the-Knee Boots
If the plain or simple boots don’t spark your enthusiasm, consider opting for these unique alternatives. Those who crave excitement and variety in their fashion choices will likely appreciate the array of options available. Not only can you pair them with dresses in both bold and subtle hues, but you can also select a design that resonates with your personal style and effortlessly complements most of your outfits.
Keep in mind, however, that these statement-making boots are better suited for special occasions like parties, rather than everyday wear.
29 – Street Style Knee-length boots
When it comes to styling knee-length boots for winter, versatility is key. Pair them with short dresses and a black or brown jacket for a chic look that’s perfect for casual outings like shopping trips or get-togethers. The dark colors of these boots make them easy to match with most outfits, from flowy dresses to distressed jeans. However, it’s worth noting that street style boots are best saved for off-duty occasions – leave the workplace attire to more professional footwear options.
28 – Casual Look
While slightly heavier than other options on our list, these boots are a great choice if you’re looking to add some visual flair to your outfit. Bright colors are a common feature of this style, which often includes laces for added adjustability. When paired with long coats and winter dresses, these boots create a striking combination that’s perfect for colder weather.
27 – Snow Boots
With the name of the boots clearly indicating their purpose for extreme cold weather, it’s no surprise that they’re designed to keep you warm and protected from the harsh conditions. The versatility of these snow boots lies in their ability to be paired with a variety of outfits. For a timeless look, black boots can be effortlessly combined with dark blue jeans, creating a chic winter ensemble that exudes simplicity and comfort.
26 – Mid-calf Boots
For a stylish yet understated look, consider opting for light brown shades that will complement your outfit seamlessly. Mid-calf boots, although not as commonly found as other styles, offer a unique twist on traditional footwear. Their versatility allows them to be paired with both long winter dresses and jeans, making them an excellent choice for everyday wear. Plus, their comfortable design ensures you can wear them daily without sacrificing style or practicality.
25 – Cowboy boots
If you’re on the hunt for stylish footwear to impress at social gatherings, cowboy boots are an excellent choice. However, if you prefer a more understated design without sharp points or exaggerated openings, these might not be the best fit for you. That being said, they pair beautifully with jeans and darker-colored coats, making them a great addition to any party ensemble.
24 – Classic Long Brown Boots
For those seeking a sophisticated, stylish, and high-heeled boot option, this particular style offers an excellent choice. When it comes to selecting the best color, we highly recommend opting for dark brown. This versatile shade will pair perfectly with black jeans, creating a timeless look. Notably, these boots feature pointed toes and a sleek, shiny finish.
23 – Laced Tall Boots
For those seeking versatile footwear options that can seamlessly transition between various winter ensembles, these lace-up boots are an excellent choice. Their tailored design makes them particularly suitable for young ladies who prioritize comfort and style in their footwear.
22 – Black Fur Lined Boots
When it comes to choosing the perfect boots for this winter season, incorporating fur-lined options into your selection is definitely worth considering. Not only will they provide an added layer of warmth and comfort, but the subtle heel height adds a touch of sophistication that can easily be dressed up or down. Whether you’re looking for a reliable daily companion or a stylish addition to your professional wardrobe, boots with fur lining are an excellent choice.
21 – Over-the-Knee Boots with a Dress
For those who want to incorporate long boots into their outfit, the key is finding the right skirt combination. A maxi skirt can provide a stylish contrast with the boots, creating a striking visual effect. Alternatively, you can opt for a shorter skirt that doesn’t quite reach the top of the boots, adding a touch of playfulness to your overall look. Ultimately, it comes down to personal preference.
If heels aren’t your thing, flat boots are a great option too – they offer a similar stylish appeal without sacrificing comfort.
20 – How to Wear Tall Boots with Skinny Jeans
When it comes to pairing long boots with pants, denim jeans are an excellent choice that seamlessly complements their height. A classic combination, skinny jeans and cowboy boots would make for a stylish outfit. To elevate this look further, team your jeans with a peplum top and a cute jacket for a perfect autumnal ensemble. For those who want to take this style into the colder months, check out our guide on how to wear peplum tops in winter.
19 – Half Boots for a Rainy Day
When rainy days are ahead, boots are a reliable choice to keep your feet warm and dry. While ankle booties might seem appealing, they can still allow water to seep in, leaving you uncomfortable. A better option is to opt for half-boots or knee-high boots that provide extra protection from the elements.
We appreciate this understated outfit combination featuring an oversized rain jacket, a dash of blue from a button-down shirt, and dark green pants – all perfectly complemented by warm and cozy boots.
18 – Slouchy Boots with a Wool Skirt
For a winter wardrobe staple that’s both stylish and functional, look no further than the sweater dress or skirt paired with boots. This combination not only looks great but also provides excellent warmth on chilly days. One of our favorite ways to wear this outfit is with ankle boots – a perfect pairing that exudes wintry chic. For an added layer of sophistication, try layering up and opting for slouchy dark boots to pair with your wool midi skirt.
17 – Sweater Dress and Thigh-High Boots
The epitome of chic street style is achieved when a stunning sweater dress is paired with thigh-high boots, creating a look that’s nothing short of breathtaking. The neutral color palette employed here adds an air of sophistication, while the addition of a statement coat elevates the entire ensemble to new heights. To complete the look, a high-end fashion crossbody purse and statement sunglasses are the perfect finishing touches.
16 – Wearing Knee-High Boots to Work
While knee-high boots can be a suitable choice for the office, it’s essential to select the right style. Classic knee-high boots are generally more appropriate than motorcycle or riding boots. Adding a slight heel can elevate the overall look. For a polished appearance, pair them with dark-wash jeans and a blouse, then top it off with a blazer or work jacket. To maintain a subtle and conservative aesthetic, keep the overall look simple and understated.
15 – Super High Heeled Boots
Caution is advised when donning these eye-catching over-the-knee boots, which boast impressive platform heels and make a stunning pairing with distressed denim jeans and a vibrant poncho wrap. The bold color palette, featuring deep hues of purple and red alongside mustard yellow, adds to the overall striking effect. To complete this look, add a fedora hat for an effortlessly chic finish.
14 – Dress & Coat
As the autumn season cools down, this short dress and coat combination proves to be a stylish and practical outfit choice. The baby pink coat adds a pop of color to an otherwise darker-toned ensemble, while the boots provide warmth for your legs. For a complete look, consider pairing with long shoes from our latest style collection.
13 – Chic Trousers and Coat
When working with shorter boots, a stylish solution can be found in pairing slim-fit ankle trousers with a mock neck sweater and a thigh-length wool coat. This combination provides warmth during the cold winter months while maintaining a chic appearance without overwhelming layering.
12 – Red Leather and Denim
The unconventional pairing of a chambray shirt with a denim skirt, tights, and bold red leather boots is nothing short of captivating. The effortless elegance of this look makes it perfect for a day at the office – particularly fitting for those working in the fashion sector, where creativity and self-expression are encouraged.
11 – Super Funky Style
Why not mix things up with a funkier vibe? This look is perfect for when you want to make a bold statement and turn heads. Confident fashionistas will adore this option, but remember to balance it out with the rest of your outfit so you don’t go overboard. Perfect for those who aren’t afraid to express themselves through their clothing choices.
10 – Furry Hat, Leather Leggings, Checked Shirt
What’s not to love about this street-style look? It’s a masterclass in mixing textures and playing with monochromatic tones. From the supple leather of the bag and leggings to the plush cap and soft shirt, every element is designed to delight the senses as much as the eyes. The combination of smooth and rough, hard and soft creates a visual feast that’s sure to turn heads. And at the heart of it all are the thigh-high boots – the perfect finishing touch for this stylish yet laid-back ensemble.
9 – Leather Trousers and Three-Quarter-Length Sleeves
The latest fashion trends are often inspired by the catwalk, and this outfit is no exception. The striking combination of cool-toned blues and sleek footwear is a perfect blend of style and sophistication. If you’re looking to incorporate similar elements into your wardrobe, consider checking out 17 trendy leather pants that have made a splash this season.
8 – Street Style with Long Boots
The striking visual appeal of this outfit evokes a strong desire to emulate its eclectic style, blending effortlessly with the urban landscape as we envision ourselves rocking similar grunge-inspired looks.
7 – Ripped Jeans and a Striped Top
A striped button-down shirt is an effortless choice for everyday or weekend wear. To take your outfit to the next level, pair it with a pair of skinny ripped jeans and add some boots for a chic, laid-back look that exudes confidence. If you’re looking for more inspiration, be sure to check out our post on distressed denim trends.
6 – Simple, Cute Look for Every Day
Stashing a few versatile outfits in your wardrobe can be a lifesaver on those days when you’re looking for something more stylish than hoodies and sweatpants. This particular look is perfect for occasions where you want to feel put together without feeling too dressed up. The timeless combination of knee-high boots with jeans, for instance, never goes out of style. Whether you’re running errands or just lounging around, this outfit will keep you looking great and confident.
5 – Thick-Striped Sweater and Oversized Bag
This effortless look is perfect for casual outings with friends or family gatherings. The combination of a soft sweater paired with colored jeans creates a stylish yet comfortable ensemble that’s ideal for daytime events. To add some rugged charm, pair it with knee-high brown leather boots and an oversized tote bag. Don’t forget to complete the look with statement-making accessories – a chunky necklace adds visual interest while simple drop earrings provide a touch of understated elegance.
4 – Sheer Top and Patterned Leggings
Elevate your weekend wardrobe with a simple yet stylish ensemble. For busy moms on-the-go, this look is a perfect blend of comfort and chic. A sheer top takes center stage, offering a fresh alternative to the usual sweater or tee. When paired with patterned or print leggings, it creates a visually appealing combination that’s sure to turn heads. Add a touch of whimsy with a funky necklace, and finish off the look with your favorite boots.
Whether you’re running errands at Target or spending time with your little ones at the playground, this effortless outfit is sure to make you feel like the belle of the ball.
3 – Patterned Skirt with Boots
To pull off the perfect boots-and-skirt combo, start by opting for a skirt that hits just above, at, or slightly below the knee. This versatile length allows for effortless styling with a cute top. When pairing your skirt with brown leather boots and a flat clutch, you’ll create a charming ensemble suitable for everything from Sunday services to casual gatherings with friends.
2 – Celebrity Hailey Bieber Inspiration
Hailey Bieber’s effortless style is on full display as she pairs stunning thigh-high boots with a casual tee-shirt dress and a soft, camel-colored coat that falls just above the ankle. Her sleek top knot adds a touch of sophistication to her overall look, which is further elevated by her cute purse. This chic ensemble is proof that even superstars can rock a laid-back vibe while still looking fabulous.
1 – Vanessa Hudgens Boot Style
Vanessa Hudgens’ effortless charm extends to her impeccable fashion sense, as seen in this laid-back yet stylish ensemble. The actress effortlessly blends comfort with glamour, showcasing a versatile wardrobe that’s perfect for both festival vibes and everyday wear. Her outfit of choice features a winning combination of black long boots, low-rise jeans, a midriff-baring top, and a cardigan – all topped off with a statement scarf and bag.
This effortless look is a masterclass in creating a polished yet relaxed aesthetic that’s sure to inspire your own personal style.
Frequently Asked Questions
Long boots can be a stylish addition to any wardrobe, but knowing how to wear them can be overwhelming. Here are some frequently asked questions about styling long boots, along with expert advice on how to make the most of this fashion staple. For going out, opt for a heeled boot that fits closely against your calf. Pair it with a short dress and tights or a sweater dress, adding accessories and a fun shade of lipstick to elevate the look.
When dressing down, flat knee-high boots are a great choice. Try pairing them with leggings and a sweater or jeans and a favorite top. While some may think long boots are only for cold weather, they can actually be worn in summer too. It depends on your location, but if you live in an area where the temperature is bearable during the summer months, then go ahead and give it a try! Avoid thigh-high boots or those with fur, and instead opt for thin socks to combat moisture.
Pair them with lightweight, breathable outfits like short shorts or a mini skirt. For the office, long boots can be a great choice too. Stick to more conservative ensembles by opting for sleek black boots or leather brown ones. A little heel is also suitable, and you can pair it with a skirt and tights, over dark-wash jeans, or with a high-neck dress. When it comes to wearing long boots with jeans, it’s all about finding the right combination.
Try pairing them with blue or black jeans and knee-length dark shade boots. Avoid light-colored boots with light-colored jeans for a more polished look. Finally, don’t be afraid to wear boots with dresses! It depends on the length of the dress, but generally speaking, ankle-length boots work well with long dresses while knee-length boots can add a stylish touch to short dresses.
