Boots are the ultimate versatile footwear. With so many styles to choose from, it can be tricky to figure out what to wear them with and how to style them. If you’re short on time, here’s a quick answer: boots look great with jeans, leggings, dresses, skirts, and shorts.

Pairing them with thick tights or knee-high socks will also allow you to wear them in colder weather.

In this comprehensive guide, we’ll cover everything you need to know about wearing boots in any season and for any occasion. You’ll learn the best boot styles to wear with various bottoms, tips for styling boots in summer vs winter, and how to dress up boots or wear them casually.


When it comes to pairing boots with jeans, there are several options to consider. Whether you prefer a sleek and slim silhouette or a more relaxed and casual look, there is a perfect style of jeans to complement your boots.

Skinny jeans

Skinny jeans are a versatile option that can be paired with various types of boots. The form-fitting style of these jeans creates a sleek and streamlined look when tucked into ankle or knee-high boots. This combination is perfect for showcasing your boots and creating a chic and fashionable outfit.

For a more casual look, you can also cuff the bottom of your skinny jeans and wear them with ankle boots.

Bootcut & straight leg jeans

Bootcut and straight leg jeans are another great choice for pairing with boots. These styles provide a slightly looser fit, allowing you to easily tuck them into your boots. Bootcut jeans, as the name suggests, have a slight flare at the bottom which helps to balance out the bulkiness of certain boot styles.

Straight leg jeans, on the other hand, offer a more tailored and polished look. Both options work well with ankle, mid-calf, and knee-high boots.

Boyfriend jeans

If you prefer a more relaxed and casual look, boyfriend jeans are an excellent choice. These jeans have a loose and slouchy fit, giving off a laid-back vibe. When pairing them with boots, you can choose to either roll up the cuffs or tuck them in for a more polished look.

Boyfriend jeans look great with ankle boots, combat boots, and even knee-high boots for a stylish and effortless ensemble.

Remember, the key to successfully pairing boots with jeans is to find the right fit and style that flatters your body shape and complements the boots you are wearing. Experiment with different combinations and don’t be afraid to step out of your comfort zone to create unique and fashionable outfits.


Ankle boots with leggings

Leggings are a versatile and comfortable choice for any casual outfit. When it comes to pairing leggings with ankle boots, the key is to create a balanced and stylish look. One popular combination is to wear ankle boots with leggings and a long tunic or oversized sweater.

This creates a chic and effortless look that is perfect for running errands or meeting friends for coffee. Another option is to wear ankle boots with leggings and a leather jacket for a more edgy and bold style.

The contrast between the sleek leggings and the rugged boots can create a fashionable and eye-catching outfit.

Over-the-knee boots with leggings

Over-the-knee boots are a trendy and statement-making footwear choice. When paired with leggings, they can create a fashion-forward and confident look. One way to style over-the-knee boots with leggings is to wear them with a long, oversized sweater or cardigan.

This creates a cozy and stylish outfit that is perfect for colder weather. Another option is to pair over-the-knee boots with leggings and a mini dress or tunic. This combination adds a touch of femininity to the look while still maintaining a trendy and fashionable vibe.

Dresses & Skirts

Mini dresses & skirts

Boots can be a stylish and versatile choice when paired with mini dresses and skirts. Whether you’re going for a casual or dressy look, there are many options to consider. For a casual daytime outfit, try pairing a floral mini dress with ankle boots.

This combination creates a playful and feminine look. If you’re looking for a more edgy vibe, opt for a leather mini skirt paired with knee-high boots. This combination exudes confidence and adds a touch of rock ‘n’ roll to your outfit.

Midi dresses & skirts

Midi dresses and skirts are a popular choice for both formal and casual occasions. When it comes to pairing boots with midi-length pieces, there are various options to explore. For a chic and sophisticated look, consider pairing a pleated midi skirt with heeled ankle boots.

This combination elongates the legs and creates a sleek silhouette. If you’re aiming for a more bohemian vibe, try a flowy midi dress paired with slouchy suede boots. This combination is effortlessly stylish and perfect for a laid-back day out.

Maxi dresses & skirts

Maxi dresses and skirts are known for their elegant and feminine appeal. When it comes to choosing the right boots to wear with maxis, there are a few key considerations. One option is to pair your maxi with knee-high boots.

This combination creates a trendy and bohemian look, perfect for festivals or outdoor events. Another option is to opt for ankle boots with a stacked heel. This combination adds a touch of sophistication to your maxi dress and is great for more formal occasions.

Remember, when styling dresses and skirts with boots, it’s important to consider the length and style of the dress or skirt, as well as the occasion. Experiment with different combinations to find the look that best suits your personal style and body shape.

So, go ahead and have fun creating stylish outfits with your favorite boots!


Boots are not commonly associated with shorts, but when styled correctly, they can add a touch of edginess and personality to your outfit. Here are some ideas on how to wear boots with different types of shorts:

Denim shorts

Denim shorts are a classic summer staple, and they can be paired with various types of boots for a cool and casual look. An excellent option is to wear ankle boots with denim shorts. The combination of the ruggedness of the boots and the laid-back vibe of the shorts creates a perfect balance.

You can opt for a cropped or cuffed denim shorts style to show off your boots. Complete the look with a graphic tee and a denim jacket for a trendy and effortless outfit.

Athletic shorts

Who says you can’t wear boots with athletic shorts? This unexpected combination can add a unique twist to your sporty look. Pairing chunky combat boots with athletic shorts creates an interesting contrast between the casual and rugged boot style and the sporty shorts.

Add a loose-fitting t-shirt and a baseball cap to complete the ensemble. It’s a great way to elevate your athletic wear and make a fashion statement.

Dressy shorts

For a more sophisticated and polished look, dressy shorts can be paired with ankle boots or heeled booties. This combination works well for a dressier occasion or a night out. Opt for tailored shorts in a flowy fabric like silk or satin.

Pair them with sleek ankle boots or heeled booties to add a touch of elegance. Complete the look with a blouse or a blazer for a chic and fashionable outfit.

Remember, when wearing boots with shorts, it’s essential to consider the length and style of the shorts to create a balanced and cohesive look. Experiment with different combinations and have fun with your style!

Styling Boots in Summer vs Winter

When it comes to styling boots, the seasons play a crucial role in determining the right choices for your outfits. In summer, you want to opt for lighter materials and open-toed styles to keep your feet cool and comfortable.

In contrast, winter calls for warmer options and closed-toe boots to protect your feet from the cold. Let’s explore the key differences between styling boots in these two seasons.

Open-toed vs closed-toe boots

In the summertime, open-toed boots are a great choice for those who want to add a touch of edginess to their outfits while keeping their feet cool. Open-toed boots come in various styles, including peep-toe, cut-out, and gladiator designs.

They can be paired with flowy dresses, skirts, or even shorts for a chic and fashionable look.

On the other hand, during the winter months, closed-toe boots are essential to protect your feet from the cold weather. These boots provide warmth and insulation, making them perfect for pairing with jeans, leggings, or tights.

Closed-toe boots come in a wide range of styles, such as ankle boots, knee-high boots, and over-the-knee boots, allowing you to create versatile winter outfits.

Lighter colors & materials

In summer, it’s all about embracing lighter colors and materials. Opt for boots in neutral shades like beige, tan, or white, as they can be easily paired with vibrant summer outfits. Lighter materials such as canvas or suede can also provide breathability and comfort for your feet in the warmer months.

When winter arrives, it’s time to switch to darker colors and materials that offer better insulation. Black, brown, and burgundy are popular choices for winter boots as they complement the season’s color palette.

Look for boots made from leather or faux fur to keep your feet warm and protected from the elements.

Socks, tights & leggings for warmth

In the summer, you can go sockless or wear ankle socks with open-toed boots to keep your feet cool and comfortable. However, in winter, you’ll need to layer up to stay warm. Pair your closed-toe boots with cozy socks, thick tights, or leggings.

Not only will they provide insulation, but they can also add a stylish touch to your winter outfits.

Pro Tip: If you’re wearing ankle boots with dresses or skirts in the winter, opt for opaque tights in a matching color to create a streamlined look.

Remember, the key to styling boots in different seasons is to consider the weather conditions and choose appropriate materials, colors, and styles. By following these tips, you’ll be able to rock your boots all year round, whether it’s for a summer festival or a winter stroll through the snow!

Dressing Up Boots vs Casual Looks

When it comes to styling boots, there are various options to choose from depending on the occasion and your personal style. Whether you want to dress up your boots for a formal event or keep it casual for a day out with friends, here are some key factors to consider.

Heels vs Flat Boots

One of the first decisions to make when styling boots is whether to go for heels or flat boots. Heeled boots can instantly elevate your outfit, adding a touch of sophistication and glamour. They are perfect for dressing up an ensemble for a night out or a special occasion.

On the other hand, flat boots offer a more relaxed and casual look. They are great for everyday wear and can be paired with jeans, leggings, or dresses for a comfortable yet stylish look.

Leather vs Suede

Another factor to consider when styling boots is the material. Leather boots are timeless and versatile, making them a classic choice for both dressy and casual looks. They are durable, easy to clean, and can withstand various weather conditions.

Suede boots, on the other hand, have a softer and more luxurious texture. They add a touch of elegance to any outfit and are perfect for creating a chic and sophisticated look. However, suede boots require more care and attention to maintain their appearance.

Monochrome Outfits

One stylish way to wear boots is by opting for monochrome outfits. Pairing your boots with an outfit of the same or similar color can create a sleek and cohesive look. For example, black boots paired with black jeans and a black sweater can create a slimming and stylish silhouette.

This minimalist approach allows your boots to become the focal point of your outfit. Additionally, monochrome outfits can make you look taller and leaner, adding an extra touch of confidence to your overall look.

For more inspiration and ideas on how to style your boots, you can check out fashion websites such as Vogue or Harper’s Bazaar.


With so many options, you can see that boots are an extremely versatile shoe choice. Follow these tips to help inspire your outfit creations. The most important rule is to have fun with your style – mix, match, and layer boot looks to perfectly suit your personal taste and the occasion.

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