The Best Boot Trend to Wear With a Minidress in 2026 Was Considered "Dated" a Year Ago

I've worked in the fashion industry for over six years, but sometimes I forget how quickly trends can come full circle. Take thigh-high, heeled boots, for example. Just a year ago, they might have felt dated, but in 2026, they're suddenly cool again—even when styled with a minidress. Case in point: Jennifer Lopez's recent outfit.

This week, after announcing the release of her new single, "Proof of Love," J.Lo shared photos on Instagram showcasing a stylish look. She wore a long-sleeve Valentino minidress with a cummerbund, pairing it with oversize sunglasses, a clutch, and thigh-high boots.

On Jennifer Lopez: Valentino dress and belt; Marina De Golle bag; vintage David Webb jewelry

J.Lo's outfit is a perfect example of how to make over-the-knee boots and a minidress feel modern and elevated. The key lies in the details. Choosing boots in a luxurious material, such as lambskin leather, creates an expensive look, while a pointed toe elongates the leg and adds a refined touch. Her neutral styling also plays a major role, with warm hues of gold, camel, and ivory coming together to create a polished effect.

If you needed proof that the once-perceived "dated" boot trend is back and worth styling with your fall and winter dresses in 2026, this is it. Keep scrolling to shop the chicest styles.

Shop the Best Thigh-High Boots