Will A Guy Look Weird For Wearing Cowboy Boots In The City? A Guide To Wearing Cowboy Boots In The City

Cowboy boots have appeared in various Western films, but what is the accurate tale behind them? Of course, they’re more than simply a fashion statement. In their original shape, Cowboy boots were a lifesaver for working men.

Cowboys in the past needed practical, cheap footwear that they could wear while on the job. They made it possible for cowboys to ride and walk in tandem with equal support and comfort. Cowboy boots’ main design is for labor purposes, but others are more upscale for special occasions and celebrations. Even with the popularity of cowboy boots, the modern city guy has his reservations about donning them. He is not sure if he will look stylish or plain weird.

Will I Look Weird If I Wear Cowboy Boots In The City?  

You won’t. You can wear cowboy boots without looking country. After all, this on-trend footwear is more than simply a pair of boots. They are timeless items of footwear having a long history of use dating back centuries.

Cowboy boots should be your particular favorite. They bring out the trim, sleek appearance in you when worn correctly. “When worn well” is the take-home element of my phrase. So how can you wear cowboy boots without seeming like a jerk? That is an excellent question. Cowboy boots look great with skinny bootcut jeans or pants that aren’t too long or too short. They look well with gray, black, or brown slacks or jeans. Where should cowboy boots be worn? Please, for the love of God, don’t believe you need to go to a Kenny Chesney or Dolly Patron concert to rock your cowboy buddies. No, cowboy boots are acceptable attire for pubs, weddings, county fairs, rock concerts, and serious business meetings.

Feel comfortable if you want to add cowboy boots to your collection but aren’t sure what to match them with or how to wear them. The purpose of this page is to assist that city guy who has always wanted to wear cowboy boots but isn’t sure how.

Let’s get started, shall we?

A City Man’s Guide To Style Cowboy Boots  

1. Collared Plaid Shirts 

Plaid is currently into two divisions: those who regard it as a primary, fashionable need, and others who see it as a sartorial icon of that shudder-inducing neologism, the ‘hipster.’ However, dismissing plaid shirts as simply another outdated fad would be a mistake, given their history and endurance.

The key to wearing plaid patterns is to keep the rest of your outfit basic; plaid is a vibrant, vivid pattern, so let it speak for itself by pairing it with neutral hues that complement your shirt’s palette.

The collared Plaid shirt is a staple of the urban aesthetic. A plaid shirt and a pair of cowboy boots look great together. Wear a plaid shirt jacket or a flannel shirt over your tee, jeans, and cowboy boots combo for a more contemporary and laid-back look.

2. Wear A Denim Shirt

A denim shirt is a current closet essential for any man. Denim shirts come in various hues and materials, making them a flexible option. Dark indigo and black offer a more formal atmosphere, while light blue and acid washes give a more laid-back attitude. Short-sleeved versions are ideal for summertime, while long-sleeved types are ideal for layering when the weather gets cold. Slim fit styles create a more modern silhouette, and loose fits make a more comfortable vibe. For extra individuality, look for elements like tonal quilting and contrast seams.

Combine a short-sleeve chambray shirt with slim-cut chino shorts and low canvas shoes for a simple cool look. Wear your chambray shirt with rolled sleeves, black denim trousers, and cowboy boots for a more practical approach and refined look.

3. Wear A Suit

Nothing looks better on the city streets and boardrooms than a magnificent pair of handstitched cowboy boots paired with a custom-made men’s suit. Well-made cowboy boots may be worn in almost any scenario and almost everywhere. American heads of state from Ronald Reagan to George W. Bush have all embraced this style in the halls of the White House. 

Generally, the answer is a yes if you’re contemplating if a pair of wonderfully constructed handcrafted cowboy boots will go well with the custom-made suit you just bought from Adams Baker designers. Wearing cowboy boots with a suit is not only stylish, but it will also set you apart from other men. Who hates being the best-dressed man in the room?  

4. Wear A Leather Jacket

Call it style, funkiness, class, originality, or bad boy fad, but leather has an attitude that fabric lacks.

The beauty of leather is that it has a tough-guy image that is ageless rather than fashionable. Because people have relied on leather material since the dawn of time, we connect leather jackets with toughness. It’s not a manufactured look as shredded jeans or metal studs are. So, even if it’s a very smooth and sophisticated jacket design, a leather jacket gives users an impression of toughness, competence, and edginess. The leather jacket is a great companion to the cowboy boots, and it exudes a modern vibe.

Where To Wear Your Cowboy Boots

1. Salsa, square, and other types of step dance

2. Bars

3. Restaurants with a relaxed atmosphere

4. Fairs held by counties, states, grange associations, and other groups

5. Concerts of rock and country music

6. Picnics with a loved one on a romantic evening

7. Comedy shows

8. Going for horse riding.

Where To Avoid Wearing Cowboy Boots

1. When going for a first date

2. When attending political functions

3. When giving a speech.

4. When going on long treks or driving

5. When attending performances in a high-end theater

6. When attending games and Sports events


Any guy who chooses to avoid being basic and slips his feet into a pair of cowboy boots understands what it means to be high-quality. This guy is the type of fellow who will not accept anything less than the best.

When you see a man wearing a pair of genuine cowboy boots, you know he appreciates quality. He isn’t going to the store and buying whatever is on the shelf. Instead, he’ll most likely spend time investigating and evaluating his alternatives so that he may pick the best of the best. Each man should own a pair of cowboy boots.

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