The Drop-Waist Dress Trend Is Made for Late-Summer Romance

Key Takeaways

• One of this season’s top dress trends is the drop-waist, which has been a fixture since the 1920s but returned to popularity as a result of bridal trends and a resurgence in sophisticated retro aesthetics.
• The silhouette transitions seamlessly from summer to fall looks, especially when accessorized dramatically and layered with your favorite cardigan or blazer.

Drop-waist dresses have become a staple part of summer 2025’s uniform, but to say they’re making a comeback is only partially true. Since its inception a century ago, some form of the drop-waist, whether a subtle, just-below-the-hip placement or a dress that dramatically blooms mid-thigh, has been present on runways and department store clothing racks alike.

That being said, experimental iterations of the drop-waist dress have had their moment this summer—and with fashion month approaching, we’re expecting to see even more of this transitional season-friendly look. Below, we examine the evolution and appeal of the drop-waist trend, plus styling tips and product picks to nail the statement.

The History of Drop-Waist Dresses

Although they’ve received a modern touch recently, the drop-waist dress’s inception dates back to the 1920s flapper era. Like many classic styles we love today (including the timeless little black dress), drop-waist dresses became popular thanks to the It girls of a full century ago. Their first iterations typically had looser, tubular silhouettes on the upper half and blossomed into a fuller skirt, being one of the first garments in women’s fashion to go against more restrictive ideals.

The drop-waist silhouette was more than just a dress—it was a symbol of women’s liberation and the fight against harmful societal norms. This overall trend for looser-fitting clothing, called “La Garçonne,” was popularized by none other than Coco Chanel.

Drop-waist dresses became a fashion staple for decades to come, especially in the mid-to-late 1960s alongside other looser-fit pieces in the popular “mod style category,” such as shift dresses. Many of the time’s biggest fashion tastemakers—like Audrey Hepburn and Jackie Kennedy Onassis—embraced shorter renditions of the drop-waist dress, complete with bolder color patterns reflective of the time.

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The Drop-Waist Dress Trend in 2025

Once a key style for representing rebellion and independence, the drop-waist dress surprisingly found popularity in bridal fashion, particularly in 2024, thanks to modern designers like Danielle Frankel. The look has since found its way out of the chapel and into the closets of this era’s most stylish people, albeit with less matrimonial designs.

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Modern drop-waist dresses have a sophisticated retro feel, fitting in alongside other trends of the moment like east-west handbags and caftans. The silhouette has become a go-to for office looks and swanky brunch ensembles, plus it’s had multiple red carpet moments on a roll call of stylish celebs, including Rihanna, Demi Moore, Rachel Zegler, Lana Del Rey, and Irina Shayk.

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Need we say more? Considering it’s one of the more practical dresses to wear as we approach fall, we’re expecting to see even more maxi dress iterations of the drop-waist as the temperature cools down.

How to Style

The beauty of a drop-waist dress is its versatility: It’s basically the Swiss army knife of your closet. This style comes in midi and mini lengths for warm-weather adventures, but for a style that’s versatile year-round, a maxi silhouette adds drama with surprising mileage.

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During the dog days of summer, feel free to wear your drop-waist dress on its own with oversized sunglasses and your favorite accent jewelry. As we approach chillier fall days, many of these dresses adapt well when layered with a cozy cardigan or blazer.

This dress silhouette practically begs to be paired with a closed-toe shoe, so don’t be afraid to style yours with your favorite knee-high boots, ballet flats, or mules. From there, just add a statement top-handle bag for a winning dose of everyday glamour that you can take to dinner parties, fashion week, and beyond.

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Standout Drop-Waist Dresses to Shop

The drop-waist dress revival is just getting started. The proof is in the stockpile of designs going viral, including Aritzia’s color-blocked take and Abercrombie & Fitch’s dipped-line midi. Below are a few modernized takes on the classic trend, including structured nods to its looser-fitting past and romantic, end-of-summer-worthy finds.