Old-School Fashion Trends From The 1920s That Are Making A Comeback

Vintage fashion has never been trendier. With the global rise of nostalgia for seemingly simpler times combined with a renewed interest in sustainable second-hand shopping, it's cooler than ever to look like you've just stepped out of a time machine. While many old-school fashion trends from the '30s and beyond have become popular again, we're seeing styles from even further back in history re-emerge into the mainstream today. One century ago, in the 1920s, fashion was undergoing a major shift. As cultural values slowly began to evolve, women gained more autonomy, and night life as we know it today emerged, the popular garments of the era naturally evolved to meet society's new needs. Would people of the time believe that, 100 years later, many of their looks would still be influencing mainstream fashion?

Looking at the styles that are trendy this decade, it's clear we've gone back to the Jazz Age for sartorial inspiration. Old-school styles like T-strap shoes, the drop waist silhouette, beaded handbags, and even opera gloves are just a few of the Roaring '20s contributions to modern fashion. Fashion may have changed quite a bit over the past century, but these trends — spanning 100 years of progress and innovation — have proven that they are truly timeless. 

Women have been carrying handbags for centuries. However, one of the most unique purse styles came into fashion in a major way during the 1920s: beaded bags. Women of the Roaring '20s carried handbags, clutches, and drawstring purses covered in eye-catching art deco patterns and bright colors. One century later, and we're still carrying elaborate beaded purses. 

While there are many similarities between the beaded bags of the 1920s and 2020s — like their themed designs and thin straps — some of the modern designs lean away from their vintage counterparts. These new styles include wooden beads, mini bags, and beaded top-handle bags with a thick strap. Streamlined top-handle bags are the sophisticated, timeless trend for everyone, but beaded detailing can further elevate the style. Try blending 1920s and 2020s style by wearing a beaded top-handle purse with floral embellishments, the latter of which was one of the most popular patterns of the Jazz Age. 

For early Hollywood stars in the late 1920s like Greta Garbo, opera gloves were a beloved accessory. Over-the-elbow gloves bring a dramatic flair to any look, which made them an instant hit among the most fashionable folks of the era. Today, long gloves are coming back in a big way. Throughout every fall and winter of the 2020s thus far, we've seen opera gloves return as one of the seasons' biggest trends. This is not only for their utilitarian benefits, but as a way to incorporate vintage vibes into cool-weather looks in a chic, elevated fashion.

There are plenty of ways to embrace the dramatic opera glove trend today. From ruched leather to bold pops of color, opera gloves can serve as the perfect statement piece for your next going-out ensemble. While many today still associate the old-school accessory with formal gatherings and black-tie attire (since long gloves were often worn for dressier occasions in the 19th and early 20th centuries), the 2020s are seeing opera gloves styled alongside more casual garments. Modern fashion is all about subversion — which makes opera gloves the perfect 1920s-inspired piece to feature in your regular wardrobe. 

One of fall 2026's biggest shoe trends is the humble T-strap heel. Named for the long strap that runs over the foot from the toe to the ankle, T-strap shoes have existed for over a century. In the 1920s, flappers popularized the chic shoe silhouette for its combination of streamlined style and extra support (when you're dancing the night away, you need a shoe that's as comfortable as it is stylish, after all). The style re-emerged in the 1970s and 1980s, with T-strap silhouette variations extending to flats and Mary Janes as well as heels.

Now, T-strap heels are one of the '80s shoe trends making a major 2026 comeback. The retro shoe trend is more versatile than you'd think; though the shape may seem ultra-feminine, there are ways to style it beyond expected pairings like midi skirts and dresses. Mix things up by pairing T-strap heels with exciting fabrics like fur and mesh, denim trousers, or even a flirty miniskirt. 

When you think of 1920s fashion, what comes to mind first? Next to long strings of pearls and cloche hats, drop waist dresses are likely among the top candidates. The drop waist silhouette features a lowered waist line that sits just below the hips. Reflecting growing autonomy for women, flappers couldn't get enough of androgynous-leaning silhouettes like drop waist dresses, which created a waifish effect. Throughout the mid 2020s, the drop waist shape has come back into fashion through chic dresses and skirts. 

While it isn't the first time the silhouette has re-emerged, it hasn't been this mainstream in quite some time. But, if you're nervous about embracing the drop waist dress trend, don't be. There are many ways to get in on the fun; no matter what dress shape flatters you best, from shift to A-line, you can find it in a drop waist. As one of the most prominent and long-lasting 1920s trends to make a comeback in the 2020s, drop waist dresses aren't going away anytime soon.