Best Heeled Dress Boots for Men

Heeled dress boots can be a fun alternative to traditional loafer and oxford styles. The extra lift makes a bold yet tasteful statement and is also great looking for shorter guys looking to add a few extra inches to their frame. Styles done in smooth or patent leather tend to look dressier, so you’ll want to stick to these finishes for more formal occasions. Save light-colored suede and distressed leather styles for your off-duty wardrobe. While monochromatic ankle boots are a no-fail option, Western styles are great if you’re feeling a little more daring. Ahead, shop some of our favorite heeled dress boots for men.

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1. Ariat Heritage Western Cowboy Boot

These boots are crafted from 100% leather and feature a 1.5-inch heel with an almond toe. The shoes have a mid-calf shaft and pull-on tabs at the opening, and they feature advanced torque stability shanks.

Pros: They’re available in narrow, regular and wide sizes.

Cons: They tend to run on the smaller side.

2. Florsheim Duke Side Zip Boots

These mid-calf leather boots are finished in a deep brown color and feature a 1.75-inch heel. For optimal comfort, they feature a full sock lining and are available in regular, wide, and extra-wide sizes.

Pros: A side zipper allows for easy on-and-off access.

Cons: They run on the smaller side, so you might want to purchase these in a half-size larger than your normal shoe size.