Table of Contents

• 🔧 Boot Style 1: The Classic Brown Service Boot
• 👔 Boot Style 2: The Dress Boot
• 🔨 Boot Style 3: The Work Boot
• 👢 Boot Style 4: The Black Boot
• 🎨 Boot Style 5: The Unique Boot

🔧 Boot Style 1: The Classic Brown Service Boot

The first and most versatile boot every man should own is a simple brown service boot. A great example is the Grant Stone Diesel in brown chrome leather. This boot features a mid-value brown color that’s perfect for pairing with a variety of outfits. It’s neither too dark nor too light, making it a staple that fits into numerous style categories.

When selecting a service boot, you can choose between a plain toe or a cap toe. Plain toes tend to look a bit dressier, making them suitable for professional settings. On the other hand, cap toe boots offer a rugged charm that is equally appealing. Personally, I’ve always preferred the cap toe style, which is why my first boot purchase was the Thursday Captain. Regardless of your choice, a high-quality brown service boot is a must-have in your collection.

👔 Boot Style 2: The Dress Boot

The second essential boot is a dress boot. This doesn’t have to be an ultra-formal black wingtip; it can simply be something you’d wear to a wedding or an important meeting. Many guys overlook footwear when it comes to dressing sharp, but it's one of the easiest ways to leave a good impression.

When choosing the leather color for dress boots, opt for darker shades. I personally like burgundy leather, as it’s both interesting and versatile. Burgundy pairs beautifully with jeans, green chinos, and can complement navy, charcoal, and brown suits. If your wardrobe consists mostly of charcoal and black suits, consider going with a black leather dress boot instead. My favorite dress boot is the Beckett Simonon Elliot in burgundy leather, which is stylish yet comfortable enough for dancing at weddings!

🔨 Boot Style 3: The Work Boot

Every man needs a sturdy work boot, and the color of the leather here is less critical since these boots are meant to take a beating. I lean towards brown leathers, especially lighter shades, as they show dirt and patina more easily, which I find appealing.

For work boots, you can either invest heavily in a high-quality pair or go for something more budget-friendly. Personally, I’ve been using the White’s Packer for six months for various DIY projects around the house, from sanding to fencing. While I love the build quality of the White’s Packer, it may be overkill for casual yard work. For a more affordable option, the Redwing Classic Chelsea is a comfortable choice that’s easy to slip on and off. The Thoroughgood MTO is another solid pick, despite its plastic welt, as it offers good slip resistance.

👢 Boot Style 4: The Black Boot

As you expand your collection, the fourth boot you should add is a black boot. If you often wear black t-shirts or jeans, a black boot becomes essential. While you can wear brown boots with black outfits, a black boot simply looks sharper.

Before I owned my first pair of black boots, I found myself struggling to match brown boots with black outfits. My first black boot was a sleek Chelsea, which doubles as a versatile dress boot. Currently, I’m a fan of the Grant Stone Brass Boot, which features a heavy lug commando sole for more rugged wear. If you prefer a dressier style, consider the Beckett Simonon Douglas, which resembles a Chelsea boot but adds a little flair with a buckle.

🎨 Boot Style 5: The Unique Boot

The fifth and final boot every man must have is one that reflects your personality. This should be a boot that you love, even if it doesn’t match most of your wardrobe or isn’t worn frequently. It’s about having a pair of boots that you think are cool and that make you feel confident.

For me, the Taft Dylan is a standout choice due to its unique woven leather texture. I don’t wear them often, but they always garner compliments when I do. I also enjoy my Wesco Engineers, particularly because of how the chrome leather ages and creases. The key is to explore beyond the basics and find a unique pair that resonates with your sense of style.

In conclusion, these five types of boots—classic brown service boots, dress boots, work boots, black boots, and unique boots—will cover all your style bases. With these in your wardrobe, you’ll be prepared for any occasion, whether casual, formal, or rugged. So, what are you waiting for? Start building your boot collection today!