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When to Wear Tall Boots


Parading in tall boots in the summer could leave a sweat trail on your calves from the heavy leather. Depending on the material, style and color, tall boots will generally work for three-season wear. In the winter, tall boots keep you stylish and warm. Wear them over skinny pants, under boot cut trousers or over tights with a skirt. In winter, even fashionable ladies turn to tall winter fur-lined or knit boots. During spring and fall, the weather may be mild enough for you to wear the boots comfortably with bare legs.

Dressed Down

Tall boots worn over jeans or jeggings command attention for your legs. Combine tall boots over pants with a T-shirt, tunic or belted sweater. Or pair tall boots with a flirty skirt, such as a ruffled or tiered skirt. If you're daring, try tall boots and tights with shorts for a skirt alternative.

Dressed Up

For the workplace tall boots can keep you in stride depending on the office style. Flowy or sleek dresses showcase boots loudly and proudly. Hemlines that hit the knee or below will be safe and classic, but you can show an inch or two of thigh too. Stick tall boots over capris if you want to show them off, or wear them under trousers to show just a hint of leather.


Color coordinate to look the best in your boots. You don't have to be matchy-matchy, but black boots can look too heavy on a spring day, unless you incorporate other dark elements. Camel or rust-colored boots can work with black, but chocolate brown doesn't play as nice.

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