Written by Ben Chuang

In the ever-evolving world of men's fashion, the rules of style are continually being rewritten, and the classic suit is no exception to this trend.

One sartorial choice that has gained remarkable popularity and challenged conventional norms is the art of pairing boots with a suit.

This bold and dashing combination offers a refreshing departure from traditional dress shoes and brings a rugged, contemporary edge to the refined world of formal wear.

In this blog post, we're going to delve into the fascinating realm of how to wear boots with a suit, exploring ways to master this fashion-forward look while maintaining the perfect balance between elegance and edge.

Appropriate Occasions to Wear a Suit with Boots

Are you tempted to wear boots with your suit for some contemporary flare? If so, it's essential to consider the appropriateness of this combination for various occasions. Here are some guidelines on when it's suitable to wear boots with formal clothing:

Casual Events:

Boots with a suit are an excellent choice for business casual events or gatherings. Think about wearing this combination to a relaxed evening out with friends, a semi-casual dinner date, or a weekend brunch. A pair of stylish boots can lend your suit a more laid-back and approachable appearance.

Creative Work Environments:

In creative workplaces such as advertising agencies, design studios, or tech companies, there's often more flexibility in dress codes. A suit with chukka boots can work well in these settings, allowing you to express your personal style while still maintaining a professional look. However, think carefully about donning dress boots on occasions that call for professional attire.

Autumn and Winter Seasons:

Boots are particularly practical during the colder months. Opting for a suit with boots in the fall or winter can provide warmth and comfort while maintaining stylish winter fashion. Consider pairing combat boots with a heavier suit fabric to stay warm and fashionable.

Fashion-Forward Events:

If you're attending events or gatherings with a fashion-forward crowd, you can experiment with a suit paired with black Chelsea boots. It can be a conversation starter and a way to stand out in a stylish manner.

Informal Weddings:

Some weddings, especially those with a rustic or bohemian theme, may permit dress boots with a suit. Check with the wedding dress code and the couple's own shoe preferences before donning this look.

Smart-Casual Dress Codes:

For events or settings with a smart-casual dress code, wearing boots with a suit can be a chic choice. This could include cocktail parties, art gallery openings, or upscale social gatherings such as the Kentucky Derby.

Travel and Leisure:

When traveling, especially to places with unpredictable weather, combining chukka boots with a suit can be practical and stylish. It ensures you're prepared for different conditions while looking sharp.

However, it's essential to remember that not all occasions are suitable for this style choice. Traditional and formal events like gala dinners, weddings with strict dress codes, or conference attire typically require classic dress shoes. The appropriateness of boots also depends on the style of boots you choose, the type of suit, and the overall look you're trying to achieve.

Picking the Right Suit

Wondering about how to pick the right suit? We've got you covered. Boots can be paired with various types of suits, but some suit styles and fabrics work particularly well with boot style in this combination. Here are some types of suits that go well with boots:

Tweed Suits:

Tweed suits are a classic choice to pair with boots, especially during the colder months. The rugged texture and weight of tweed complement the durability and robustness of boots. This combination is perfect for a rustic, outdoorsy look.

Slim-Fit Suits:

Slim-fit suits, which have a narrower cut, work well with boots. The streamlined silhouette of the slim pants and suit pairs nicely with the bulkier appearance of some boot styles, creating a stylish contrast. Be sure to pick out a slim-fit dress shirt to go with your outfit, and check out our online suit-size calculator.

Dark Colors:

Boots often look best with suits in darker colors. Charcoal, navy, and dark gray shirts create an elegant and harmonious contrast with grey suits in most types of boots.

Double-Breasted Suits:

Double-breasted suits exude a sense of formality, but when paired with the right boots, they can create a balanced mix of classic and contemporary styles. Opt for sleek, well-polished boots to complement the sophistication of a double-breasted suit. Power suits are often double-breasted and can look great with the right pair of boots. 

Patterned Suits:

Suits or shirts with subtle patterns like herringbone or gingham can work beautifully with boots. The combination adds depth and visual interest to your overall look.

Monochromatic Looks:

Creating a monochromatic look with your suit and boots can be a sophisticated choice. For example, black boots with a black suit or dark brown chukka boots along with a brown suit can create a sleek, cohesive appearance. For more inspiration, refer to this article about the best suit colors.

How to Wear Cowboy Boots with a Suit?

Wearing cowboy boots with a suit can be a bold and stylish choice, but it requires careful execution to achieve a balanced and fashion-forward look. Here are some tips on how to wear cowboy boots with a suit:

Choose the Right Suit:

Opt for a suit that leans towards the more casual end of the spectrum. Lighter fabrics like linen, cotton, or textured wool suits, work well with cowboy boots. Darker and more formal suits may not be the best match for this style. Check out our article on the top suit brands for more information. 

Trousers Length:

Make sure the trousers of your suit are tailored to the right length. They should break just above the top of your cowboy boots, allowing the boots to be visible without excessive bunching of the fabric.

Select the Right Boots:

When wearing cowboy boots with a suit, choose a pair that is sleek and not too ornate. Classic cowboy boots with a relatively simple design and minimal embellishments tend to work best for this style. The color of the boots should complement the suit.

Belt and Accessory Coordination:

Match your belt to the color of your cowboy boots for a cohesive look. Additionally, you can add some subtle Western-inspired accessories like a leather belt buckle or a bolo tie for a touch of authenticity.

Keep the Shirt Simple:

To balance the boldness of cowboy boots, wear a simple, well-fitted dress shirt or a non-iron black button-up. This creates a contrast between the rugged boots and the more traditional suit.

Cowboy boots worn with a suit can be a standout look when done right, so feel free to experiment and adapt it to your own fashion sensibilities.

How to Wear Chelsea Boots with a Suit?

Wearing Chelsea boots with a suit is a stylish and versatile choice that adds a touch of modern elegance casual style to your outfit. Here's how to wear Chelsea boots with a suit:

Choose the Right Suit:

Opt for a suit with a slim or tailored fit. Chelsea boots tend to have a sleek and streamlined design, so a well-fitted suit complements this style. Dark suits in shades like charcoal, navy, or black work particularly well. Here's how to pair a blue suit with a black shirt.

Select the Right Chelsea Boots:

Choose Chelsea boots that are clean, minimal, and well-polished. Classic leather Chelsea boots in black or brown are timeless choices. Suede Chelsea boots can also work, especially for more relaxed occasions.

Sock Choice:

Opt for dress socks that match the color of your Chelsea boots or your suit. Coordinating the sock color with your footwear creates a seamless and polished look.

Shirt Selection:

Pair your suit with a checked dress shirt or a crisp white shirt with a tie for a formal look. Alternatively, you can wear a dress shirt without a tie or opt for a more casual shirt like a chambray or knit polo shirt for a semi-casual appearance.

 

Accessorize Well:

Add tasteful accessories like a tie clip or pocket square to enhance the overall sophistication of the outfit. The choice of accessories can help you strike the right balance between formal and casual.

This combination offers a fashionable and sophisticated alternative to traditional dress shoes, so feel free to adapt it to your individual preferences and the specific dress code of the occasion.

Frequently asked questions about matching dark boots with a suit

Can you wear chukka boots with suit pants?

Yes, you can wear suede chukka boots with a suit, and it's a stylish and versatile choice for a smart-casual or semi-formal look. The key is to select a well-fitted suit in a contemporary style and pair it with clean, minimal chukka boots in leather or suede. This combination works particularly well for events or settings with a smart-casual dress code, and it offers a modern twist to traditional suiting.

Can you wear desert boots with a suit?

Yes, you can wear desert boots with a suit, but it's essential to choose the right suit and setting. Desert boots, with their casual and comfortable design, are best suited for smart-casual or more relaxed occasions. Opt for a lightweight, unstructured suit in a complementary color, like khaki or light gray, and make sure the suit trousers are tailored to have a slight break above the top of the desert boots.

What suit colors pair well with boots?

Try wearing a charcoal, black, or navy suit with your boots. Medium gray or dark blue suit and brown suits also harmonize well when you wear dress boots. For a more casual or rugged appearance, lighter suits in shades like khaki, light gray, or tan can be a superb match for boots, adding a touch of relaxed sophistication to your ensemble.