How to Dress Like a Cowboy

There's something timeless about the cowboy aesthetic. Whether you're heading to a country music festival, working on a ranch, or simply love the rugged, classic look, dressing like a cowboy is all about combining style with functionality. At Dunder Don Workwear, we specialize in vintage, western, and work clothing to help you achieve that authentic cowboy look. This guide, approved by the Dunder Don himself, will walk you through the essential pieces of cowboy attire, from the iconic cowboy hat to the sturdy boots, and offer tips on how to choose and style each item. Get ready to embrace the cowboy spirit with confidence and flair, just like the Don would!

1. The Cowboy Hat

No cowboy outfit is complete without the iconic cowboy hat. It's both a practical and stylish accessory that protects you from the sun and adds a distinctive touch to your ensemble. Here's how to choose the perfect cowboy hat:

Choosing the Right Material

• Felt Hats: These are great for cooler weather and provide excellent durability. They're often more formal and can be worn year-round.
• Straw Hats: Ideal for the summer, straw hats are lightweight and breathable, perfect for keeping cool in hot weather.

Selecting the Shape and Style

• Cattleman Crease: The most traditional cowboy hat shape, with a single crease down the center and side dents.
• Gus Crease: A popular style with a higher crown and a deeper front crease.
• Tear Drop: Features a pinch front and a teardrop-shaped crown.

Sizing Your Cowboy Hat

A well-fitted hat should sit comfortably on your head without being too tight or too loose. Measure your head's circumference and consult the brand's sizing chart for the best fit.

Recommended Brands

• Stetson: Known for their high-quality, durable hats with a rich history dating back to 1865.
• Resistol: Offers a wide range of styles and is a favorite among professional cowboys.
• Charlie 1 Horse: Known for their fashionable designs and distinctive brand.

Hat Care Tips

• Storing: Store your hat in a cool, dry place, ideally on a hat rack to maintain its shape.
• Cleaning: Use a soft brush to remove dust and dirt. For felt hats, a damp cloth can help with deeper cleaning.

Shop Cowboy Hats at Dunder Don Workwear

2. The Western Shirt

A classic western shirt is a staple in any cowboy wardrobe. It's not just about style; these shirts are designed for durability and comfort, making them perfect for both work and leisure. Here's how to choose the ideal western shirt:

Key Features to Look For

• Pearl Snap Buttons: These buttons are a signature feature of western shirts, offering both functionality and a distinctive look.
• Intricate Stitching: Look for decorative stitching on the yokes, pockets, and cuffs for an authentic western aesthetic.
• Bold Patterns: Plaid, paisley, and solid colors are popular choices. Don't shy away from bold patterns that showcase your personality.

Choosing the Right Fit

• Slim Fit: Offers a more modern, tailored look, perfect for a sleek silhouette.
• Regular Fit: Provides comfort and ease of movement, ideal for daily wear and work activities.
• Relaxed Fit: Extra room for maximum comfort, making it a great choice for long days on the ranch.

Recommended Brands

• Wrangler: Known for their durable and stylish western wear, Wrangler shirts are a favorite among cowboys and country enthusiasts.
• Plains: Offers a range of high-quality, classic western shirts with traditional designs.
• Ely Cattleman: Renowned for their authentic western shirts, featuring detailed embroidery and durable fabrics.

Styling Tips

• Tuck In or Out: Tuck in your shirt for a polished look or leave it untucked for a more relaxed style.
• Layering: Pair your western shirt with a denim or leather jacket for added warmth and style.
• Accessorize: Add a bolo tie or a bandana to complete the western look.

Browse Our Vintage Western Shirts

3. The Jeans

Sturdy, well-fitted jeans are essential for any cowboy outfit. They provide the durability needed for tough tasks while offering comfort and style. Here’s what you need to know about selecting the perfect pair of cowboy jeans:

Key Features to Look For

• Durability: Cowboy jeans should be made from high-quality denim that can withstand heavy use.
• Fit: The fit should be comfortable and allow for easy movement, whether you're riding a horse or working on the ranch.
• Rise: Mid-rise and high-rise jeans are popular choices for cowboys as they offer a secure fit around the waist.

Choosing the Right Fit

• Slim Fit: Offers a more tailored look without being too tight. Ideal for a sleek silhouette.
• Regular Fit: Provides a balanced fit that’s neither too tight nor too loose, perfect for everyday wear.
• Relaxed Fit: Extra room in the seat and thigh areas for maximum comfort, making them great for long days of work.

Recommended Brands

• Wrangler: Known for their rugged and durable jeans, Wrangler has been a go-to brand for cowboys for decades. Their jeans offer excellent comfort and durability, perfect for both work and casual wear.
• Levi’s: An iconic brand, Levi’s jeans are celebrated for their quality and timeless style. They offer a range of fits and styles, ensuring there’s something for everyone.
• Ariat: While relatively newer, Ariat has quickly made a name for itself with jeans that combine innovative design with classic western style. Their jeans are known for their durability and comfort.

Styling Tips

• Boot Cut: Boot cut jeans are a traditional choice, designed to fit comfortably over cowboy boots.
• Straight Leg: Offers a modern look while still being practical for wearing with boots.
• Dark Wash vs. Light Wash: Dark wash jeans are versatile and can be dressed up or down, while light wash jeans offer a more casual, laid-back vibe.

Explore Our Blue Jeans Collection

4. The Belt and Buckle

A wide leather belt with a standout buckle is a must-have for any cowboy outfit. Not only does it keep your jeans in place, but it also adds a touch of cowboy flair to your ensemble. Here’s how to choose the perfect belt and buckle:

Key Features to Look For in a Belt

• Material: Leather is the traditional choice for cowboy belts due to its durability and classic look. Look for full-grain leather for the highest quality.
• Width: A wider belt (around 1.5 inches or more) is typical for a cowboy style and provides a strong, durable option.
• Detailing: Intricate tooling, embossing, or stitching can add a personalized touch to your belt.

Choosing the Right Buckle

• Size: Cowboy buckles come in various sizes. Larger buckles are more traditional and make a bold statement, while smaller buckles offer a more understated look.
• Design: Buckles often feature western motifs such as stars, horses, and rodeo scenes. Choose a design that reflects your personal style and interests.
• Interchangeable: Consider belts that allow for interchangeable buckles so you can easily switch up your look.

Recommended Brands

• Nocona: Known for their high-quality leather belts with classic western detailing and a wide range of buckle designs.
• Justin: Offers durable belts with a variety of traditional western styles and motifs.
• Ariat: Known for combining style and functionality, Ariat belts are perfect for everyday wear and special occasions.

Styling Tips

• Match with Boots: Coordinate your belt with your cowboy boots for a cohesive look.
• Tuck in Your Shirt: Tucking in your shirt will showcase your belt and buckle, highlighting this key accessory.
• Layering: Add a western belt over a duster coat or long jacket for an added touch of cowboy style.

Find the Perfect Belt

5. The Boots

Cowboy boots are perhaps the most important part of the cowboy attire. They should be comfortable, durable, and stylish. Here’s what to look for when choosing the perfect pair of cowboy boots:

Key Features to Look For

• Material: High-quality leather is the standard for cowboy boots, offering durability and a classic look. Exotic leathers like ostrich, alligator, or snakeskin can add a unique touch.
• Toe Shape: Cowboy boots come in various toe shapes, including pointed, round, and square toes. The choice depends on personal preference and comfort.
• Heel Style: Traditional cowboy boots have a slightly angled heel, while roper boots have a lower, more squared-off heel.
• Shaft Height: The shaft height can vary, but it typically extends to the mid-calf, providing protection and support.

Choosing the Right Fit

• Snug Fit: Cowboy boots should fit snugly around the instep but provide enough room for your toes to move comfortably.
• Break-In Period: High-quality leather boots will have a break-in period. They should feel comfortable after a few wears.

Recommended Brands

• Dan Post: Known for their comfortable and stylish boots, Dan Post combines traditional craftsmanship with modern comfort features.
• Tony Lama: Offers a wide range of cowboy boots known for their high quality and intricate designs.
• Ariat: Renowned for their innovative technology and comfort, Ariat boots are perfect for both work and casual wear.
• Justin: A classic brand with a long history, Justin boots are known for their durability and timeless style.
• Wolverine: While primarily known for their work boots, Wolverine also offers stylish and durable cowboy boots.
• Thorogood: Known for their American-made quality, Thorogood boots offer both style and durability.

Styling Tips

• Boot Cut Jeans: Pair your cowboy boots with boot cut jeans for a traditional look. The jeans should cover the shaft of the boots.
• Polishing: Regularly polish your boots to maintain their shine and protect the leather.
• Occasions: Cowboy boots can be worn for various occasions, from casual outings to more formal events, depending on their style and design.

Shop Our Cowboy Boots

6. The Jacket

For cooler weather, a durable jacket is essential for any cowboy outfit. Jackets not only provide warmth but also add an extra layer of style to your look. Here's how to choose the perfect cowboy jacket:

Key Features to Look For

• Material: Look for jackets made from sturdy materials like denim, leather, or canvas. These materials offer durability and protection against the elements.
• Lining: For added warmth, consider jackets with insulated or sherpa linings.
• Pockets: Functional pockets are essential for carrying small tools and personal items.

Choosing the Right Style

• Denim Jackets: A classic choice, denim jackets are versatile and durable. They can be worn over a western shirt for a timeless look.
• Leather Jackets: Leather jackets add a rugged, stylish touch to your cowboy attire. They offer excellent protection against wind and cold.
• Canvas Jackets: Canvas jackets, such as those from Carhartt, are known for their durability and functionality. They are perfect for tough outdoor work.

Recommended Brands

• Carhartt: Known for their rugged and durable workwear, Carhartt jackets are a favorite among cowboys and outdoor workers. Their jackets are designed to withstand harsh conditions and offer superior comfort.
• Levi’s: Offers a range of denim jackets that are both stylish and functional. Levi’s jackets are known for their quality and classic designs.
• Schott: Renowned for their high-quality leather jackets, Schott offers styles that are both fashionable and durable.

Styling Tips

• Layering: Pair your jacket with a western shirt and a vest for added warmth and style.
• Fit: Choose a jacket that fits comfortably over your other layers without being too tight or too loose.
• Accessories: Add a bandana or a scarf for extra warmth and a touch of western flair.

Discover Our Carhartt Jackets

7. The Accessories

Don't forget the finishing touches. Accessories can elevate your cowboy look, adding both style and practicality. Here’s how to choose the perfect accessories to complete your outfit:

Key Accessories to Consider

• Bandanas: A versatile accessory, bandanas can be worn around the neck, as a headband, or even as a face mask. They add a pop of color and a touch of western flair.
• Bolo Ties: A classic western accessory, bolo ties can be worn with a dress shirt for a formal look or with a casual shirt for a more relaxed style.
• Leather Gloves: Durable and practical, leather gloves are perfect for protecting your hands while working. They also add a rugged touch to your outfit.
• Belts and Buckles: As mentioned earlier, a wide leather belt with a standout buckle is essential. Choose buckles with western motifs to reflect your personal style.
• Hats: While cowboy hats were covered earlier, consider additional hat accessories like hat bands to further customize your look.

Choosing the Right Accessories

• Functionality: Choose accessories that not only look good but also serve a practical purpose. For example, a sturdy pair of leather gloves can protect your hands during outdoor activities.
• Quality: Invest in high-quality accessories that will last. Look for items made from durable materials like leather and high-quality fabrics.
• Style: Select accessories that complement your overall look. Whether you prefer a more traditional or modern cowboy style, there are accessories to suit your taste.

Recommended Brands

• Levi’s: Offers a range of stylish bandanas and other accessories that blend seamlessly with western wear.
• Ariat: Known for their durable and practical accessories, including gloves and belts.
• Stetson: Famous for their hats, Stetson also offers a range of hat accessories to complete your cowboy look.

Styling Tips

• Mix and Match: Don't be afraid to mix and match different accessories to create a unique look that reflects your personality.
• Layering: Layering accessories, such as wearing a bandana with a bolo tie, can add depth to your outfit.
• Personalization: Customize your accessories with personal touches, such as adding unique hat bands or choosing a buckle with a special design.

Accessorize Your Look

Conclusion

Dressing like a cowboy is all about embracing rugged, timeless fashion with a touch of individuality. At Dunder Don Workwear, we offer a wide range of vintage, western, and work clothing to help you put together the perfect cowboy outfit. Whether you're aiming for a full cowboy look or just adding a few western elements to your wardrobe, our collections have everything you need. Remember, the key to a great cowboy outfit is combining practicality with style, ensuring you’re ready for anything from a day on the ranch to a night out on the town. br> As the Dunder Don always says, "A well-dressed cowboy is a confident cowboy." Explore our full range of products and discover how you can create your own unique cowboy style:

Explore our full range of products

Feel free to reach out to us with any questions or for styling advice. We're here to help you embrace your inner cowboy with confidence and style.