Drop waist dresses have always been a bit of a fashion wildcard—you either love them or find them tricky to pull off. Over the years, this style has had its ups and downs. The flappers of the 1920s embraced the look with long, flowing designs, while later generations preferred shorter versions. Eventually, women started adding belts and sashes to define the silhouette. Then, for a long time, the trend disappeared—only to resurface in 2012. While some were skeptical about its loose shape, with the right styling, it proved to be a chic and wearable option.
Now, the drop waist dress is making a comeback once again. The key to pulling it off? Opt for a shorter length. Longer versions can look too much like a flapper costume, which is great for a themed party but not for everyday wear. If you prefer a bit more coverage, a midi length is a good compromise. However, the most modern and flattering take on this style is a shorter hemline.
Today’s drop waist dresses are far more versatile than their heavily embellished predecessors. They can be dressed up or down, depending on the occasion. A casual jersey version, like the one from Caslon, is perfect for throwing over a swimsuit at the beach. On the other hand, a long-sleeved, collegiate-inspired style from Aqua is great for a casual lunch or a stroll around campus. For a more formal event, a lace dress from Sam Edelman adds an elegant touch.
While the drop waist dress still carries a vintage vibe, it can easily be updated with modern styling. A simple version from Verdusa gets a fresh, edgy twist when paired with sleek ankle boots. Another option is to choose a design that incorporates current trends without going overboard, like a breezy BCBGMAXAZRIA dress with cold-shoulder details—perfect for warm weather.
When shopping for a drop waist dress, avoid styles that are too form-fitting. The beauty of this silhouette lies in its relaxed, effortless shape. A looser fit stays true to the original design and enhances its unique appeal.
If you’re unsure how to style this look, take inspiration from fashion influencers. One example is a handmade velvet drop waist dress styled with knee-high boots and a self-tie neckline, making it office-appropriate for creative workspaces. Another approach is to pair a patterned dress with neutral tall boots for a seamless, polished look. For a more laid-back, boho-inspired outfit, a simple drop waist dress can be effortlessly styled for an off-duty day.
With the right approach, the drop waist dress can be a stylish and versatile addition to any wardrobe.