I freaking love boots. In my opinion, they’re one of the most masculine, versatile, badass footwear options a guy can own.
Boots can make you look taller, sharper, sexier, and more confident—but only if you’re wearing the right boot with the right outfit. The problem is that a lot of guys get one piece of the equation wrong: the boot is too casual for the outfit, the pants don’t work with the boot, or the style is simply too bulky or awkward.
Here’s how to look BETTER in boots!
- The first rule is that your boot’s dress level needs to match your outfit’s dress level. A chunky lug-sole boot is casual and belongs with denim, heavier chinos, cargos, flannels, and other rugged pieces. A sleek Chelsea boot or polished dress boot can work with nicer jeans, slacks, sport coats, and even a suit. Suede automatically makes a boot feel a little more relaxed, while smoother, shinier leather tends to look more refined. The bottom line is that you need to understand what type of boot you’re buying and where it fits stylistically.
- Understand that pants really matter with boots. You don’t want the ankle opening to squeeze tightly around the boot or get caught on the laces. Chelsea boots are one of my favorites because pants naturally drape over them without creating extra bulk. Cowboy boots generally require a wider leg opening or even a boot-cut pant, while more streamlined boots work beautifully with straight or tapered pants. Whatever you’re wearing, the pants and boots need to look intentional together.
- Choose the right boot color—and coordinate your leather appropriately. When it comes to color, black is always safe, but personally, I love brown boots. Brown offers so many rich shades, textures, and tones, especially in fall and winter, and it adds depth to an outfit. You also don’t need to obsess about perfectly matching your casual boots and belt. Coordinate the colors and overall dress level, but save the precise leather matching for dressier outfits. And every guy should seriously consider owning a suede chukka—it’s simple, clean, casual, versatile, and incredibly easy to wear.
- Another major mistake is wearing boots that are just too massive. Avoid anything excessively bulky, overly pointy, or unnecessarily square-toed unless the style specifically calls for it, like certain work or cowboy boots. I generally prefer a clean almond-shaped toe that looks masculine without being clunky.
- And remember, no single boot works perfectly with everything. Ideally, I think a guy should own at least two or three different styles. If I could only choose one casual option, I’d probably go with a brown matte-leather cap-toe lace-up boot—it’s rugged, masculine, versatile, and ridiculously easy to style.
- Ultimately, boots have personalities. A rugged lace-up boot gives off an Americana, hardworking, masculine vibe. A polished dress boot feels refined and elevated. A sleek Chelsea boot tells me the guy wearing it understands style. That’s what makes boots so freaking awesome: they can be rugged and masculine, but they can also be sexy, sophisticated, elegant, and polished. The key is choosing the boot that fits your personality, your outfit, and the situation you’re walking into.
