High-Heel Trends From The '30s And Beyond You're Going To See Everywhere Again

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Nearly 100 years later, the style lessons first laid down in the 1930s are more relevant than ever. Set between the aftermath of 1920s extravagance and 1940s wartime practicality, the 1930s were a masterclass in elegance. Footwear trends reflected intricate details that leveled up classic styles, from the T strap to a snakeskin finish, and fashion gurus today are taking note. According to style coach Tami Harrigan of Exclusively Styled, it's only a matter of time before the major heel trends of the '30s are alive and well again — if they're not already. We already know that old-school fashion trends from the '30s have become popular again, so there's no reason why footwear wouldn't follow.

Harrigan points to heeled Oxford lace-ups as the most unexpected vintage trend we can expect to see more of in the coming months, but there are also other throwback styles on the horizon, from the '30s and even later. Personal stylist and image consultant Cynthia Kennedy agrees, having found emerging crazes in the '40s, the Swinging '60s, and even in the decade of disco. As the creator of Your Style Transformation Academy, Kennedy tells Glam exclusively that relying on a vintage style — like sculptural or architectural heels, for example — can add a new dimension to your look: "They're proof that sometimes the most interesting part of an outfit is what's happening below the ankle!"

To stay ahead of the curve, you might want to consider adding the following heels to your shopping list, since many vintage shoe trends made a comeback in 2026. But even if these specific shoes don't return to popularity as predicted, retro footwear featuring metallic finishes and chunky platforms can help you infuse a modern outfit with a little more character. 

Now an androgynous staple of preppy style, Oxford shoes were widespread in the 1930s. According to Tami Harrigan, heeled versions specifically might be at the beginning of a resurgence. "I love the lace ups, creative cut-outs, solid and two-tone styles," she reveals to Glam exclusively, adding that the way they fuse masculine and feminine elements makes them fit in particularly well now. "They are the perfect companion to wear with suits, oversized jackets, wide-legged jeans, and skirts." Meanwhile, flat Oxfords are one of the '80s shoe trends returning in 2026.

We can't talk about 1930s footwear without mentioning the iconic style that ruled them all: T-strap heels. The signature strap looping over the ankle emerged to replace Mary Janes in the middle of the decade, and by the looks of things, has never really left for good. "I love the fact that a design which was all the rage almost a century ago is just as relevant today," Cynthia Kennedy notes in our exclusive chat. "The delicate strap gives visual interest without overwhelming the shoe and it's a great way of infusing some vintage glamour into a modern wardrobe." To nail the luxe vintage vibe, Kennedy recommends the Kensie Odessa T-Strap Pumps.

Architectural heels might feel inherently modern and cutting-edge, but it-girls in the 1930s were all over this trend decades before many of us were born. "André Perugia, the French shoe designer, was hard at work on some gorgeous heel shapes in the 1930s, and I love seeing designers testing those same creative limits nearly 100 years later," Cynthia Kennedy tells Glam exclusively. She points to Sarah Burton's Spring/Summer 2027 line for Givenchy as a good place to look for inspo, but the more affordable JW PEI Women's Hannah Snakeskin Heel Mules absolutely get the job done.

Snakeskin shoes have made a few appearances in recent years, so this bold style might feel more modern than it is. Reptile skin was a footwear trend in the 1930s, with lizard, crocodile, and snakeskin all proving more affordable and accessible than traditional leather at the time. These days, reptile skin shoes are slowly but surely making a return, spotted on A-lister Emily Ratajkowski in August 2026. This trans-seasonal shoe style is posited to replace quieter neutrals, appearing on everything from boots to mules. 

The original foolproof ballet flat, Mary Janes have continuously popped up over the decades both in flat and heeled varieties. They were a hallmark of '20s fashion and lasted to the mid-1930s, before the innovative T-strap took over with its more detailed silhouette. But this classic style will never really be gone, now serving as a mainstay in both '90s minimalism and preppy academic styles. In 2026, heeled Mary Janes are lending a quiet refinement to casual aesthetics. Lean into the academia vibes with white socks, or wear them on their own for an elegant yet understated finish to any outfit.

Another style that is giving "futuristic" while actually being vintage, metallic heels are increasingly in-demand in the 2020s. Gold and silver footwear dominated the red carpet at the 2026 EPSY Awards, meanwhile style maven Amal Clooney was spotted donning a reflective pair of heels in October 2026. Black shoes were the style du jour in the '30s, but metallics offered a hint of Old Hollywood glamour that many dreamed of in a post-Depression world, even if they couldn't acquire it. Wear gold or silver T-straps today, and there will be no doubt about which decade you're emulating.

T-strap shoes are classic, but they did dip in popularity by the time the '40s rolled around, making way for the clean ankle strap. Cynthia Kennedy explains exclusively to Glam that ankle straps looked particularly elegant on '40s d'Orsay heels, and modern versions like the Juliet Holy Ankle Strap Heeled Sandals capture this effortless sophistication. "The cutaway sides show off just enough of the foot to create a delicate, feminine silhouette, while the ankle strap adds another beautiful design element," Kennedy adds. "They're a great alternative to a traditional pump, and I love the idea of pairing them with a tailored suit for a little unexpected glamour."

A specific subcategory of sculptural heels, comma heels have a distinctive curve that resembles their namesake. First designed in 1963 by Roger Vivier, they can be subtle, or they can lean more avant-garde. Modern iterations are often quite muted, and Cynthia Kennedy recommends the Tony Bianco Swish Heel for a style that nods to the original comma without feeling too retro. However, she tells Glam exclusively that she's anticipating a mainstream comeback: "I'd love to see more women wear this style because it's such a great way to make a statement, even when the rest of your outfit is beautifully understated."

Sky-high platform heels give away '70s style inspiration like no other shoe, and both Tami Harrigan and Cynthia Kennedy foresee this vintage icon returning to its glory in the near future. "The chunky block heels made of leather, wood, cork, and suede were the best," Harrigan tells Glam exclusively, adding, "Some versions of platform shoes have already made their way back today. But they should absolutely be brought back to wear with miniskirts, track pants and jeans." Kennedy recommends going for something like the Jessica Simpson Women's Immie Platform Sandals, which ooze fun and personality, and make for a particularly good holiday season shoe. 

It feels like we're only just appreciating quintessential '90s style now, and the perfect way to honor this iconic era is with classic square-toe strappy sandals. "The square toe made the heel comfortable to wear, while the strappy details made the shoe perfect for a night out," Tami Harrigan shares with Glam exclusively. "I still have a metallic pair in my closet now because I know they are going to make a comeback." Our expert recommends pairing them with everything from jorts to cocktail dresses, or even leather pants if you really want to embrace the '90s vibes.