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Before getting into what you shouldn’t buy, there are a few styles of boots I absolutely love: Chelsea Boots (clean, masculine, and incredibly versatile. A classic leather Chelsea with some character and patina can be dressed up or down, while a chunkier lug-sole Chelsea gives you a more rugged aesthetic), Chukka Boots (one of my favorite casual options for fall and winter. They’re simple, stylish, easy to wear, and work incredibly well with jeans or chinos), Wingtip Lace-Up Boots: (a dressier, more elevated option that’s incredibly versatile. Wear them with dark-wash jeans or chinos, and some versions can even work with a suit), Suede Wingtip Boots (lighter tan suede with a contrasting sole gives the traditional wingtip a more casual, interesting look while still staying sophisticated), and Classic Cap-Toe Boots (if you want basic badass boots, a simple brown leather cap-toe is tough to beat. It’s timeless, masculine, and easy to incorporate into your existing wardrobe).
Boots Men Should AVOID
First, avoid cheap fashion work boots. Legitimate work boots are built to take abuse, which means better construction and higher-quality materials. Cheap fashion boots designed to look like work boots usually don’t have the quality to back up the look.
Next, don’t assume expensive boots are automatically good. Look at the construction. I want to see real stitching connecting the upper and sole—not decorative fake stitching molded into rubber while each boot is basically glued together. Quality construction costs more, but it also means the boots are less likely to separate, peel, or fall apart.
I’d also avoid fake leather. Spend a little more and get the real deal. Genuine quality leather is more versatile, more stylish, lasts longer, molds to your foot, and actually starts looking better as it ages. Great leather boots develop character; cheap synthetic boots generally just look worn out.
Another huge mistake is buying uncomfortable boots because you convince yourself they’ll eventually break in. If your toes feel cramped, you feel pressure points, or your foot simply hurts when you put the boots on, don’t buy them. You may need a short adjustment period if you’re not used to something around your ankle, but fundamentally uncomfortable boots rarely become boots you love wearing.
I’m also generally not a fan of zippers on rugged boots. There are exceptions—especially with dressier boots, where an inside zipper can make sense—but if I see rugged work- or motorcycle-style boots with a big zipper on the side, they immediately feel more like fashion boots than authentic rugged boots.
One of the biggest mistakes I’ve personally made is buying boots for my imaginary life. You see an insanely cool pair and imagine yourself becoming the type of dude who wears them—but they’re six steps outside your normal aesthetic. Then they sit on the shelf. Push your style boundaries, absolutely, but be realistic. The best boots are the boots you’re actually going to wear.
And never buy boots based solely on how badass they look in an advertisement. Great photography can make cheap boots look incredible. If you see amazing “genuine leather” boots advertised for $50 or $60, something probably isn’t adding up. Quality boots cost more because quality materials and construction cost more.
I’d also avoid boots that are too pointy, have an excessively tall heel, or make your feet look gigantic. Super-thick, oversized soles can be difficult for the average guy to pull off. The same goes for extreme toe shapes. Instead, look for an almond-shaped toe—not too pointy, square, or round. It’s classic, masculine, flattering, and won’t look ridiculous five years from now.
Ultimately, every pair of boots needs to pass one final test: when I look down after putting them on, I need to think, “Damn, those are awesome.” Boots should make you feel confident. They add a little height, give an outfit a rugged, masculine edge, and can completely change how you look and feel.