The Heel Diaries: The Decades in Heels – How Style Has Evolved
Darling, if heels could talk, what stories would they tell? From shoe closets in 1920s jazz age speakeasies to stomps down the 90s supermodel runway, the history of the high heel is a saga of revolution, self-expression, courage, and, above all, glorious confidence. At Walking in Heels, we believe you can’t strut boldly into your next chapter until you understand the fabulous legacy behind every step. Whether you’re a vintage devotee or a modern magenta maximalist, today’s Heel Diaries is an invitation to journey through time—one stilettoed era at a time.
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Flapper Fabulous: The 1920s–30s – The Start of Strutting
The Roaring Twenties were a sweet spot for self-discovery and social change. As hemlines rose and dances became wilder, shoes took on a starring role. Enter the T-strap and Mary Jane—dainty, buckled, practical for high kicks but still impossibly chic. Patent leathers in black and metallics shone under city lights, while the lower heel heights made it possible to dance all night (and sneak home at sunrise).
By the 1930s, Hollywood’s golden age brought a wave of glamour. Think silver screen sirens in open-toe sandals: elegance with an undercurrent of rebellion, a bit like pouring champagne into your tea cup. Heels became narrower, and designers began experimenting with delicate ankle straps and even the first platform prototypes.
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Post-War Pin-Up: The 1940s–50s – From Utility to Ultra-Glam
War rationing might have paused peacetime decadence, but women still found ways to express themselves—sometimes with painted seams and makeshift heels. By the late 40s, as celebration and hope returned, so did eye-catching footwear. Christian Dior’s “New Look” brought wasp waists and soft lines—paired, of course, with alluringly arched pumps.
The 1950s saw icons like Marilyn Monroe and Audrey Hepburn flaunt kitten heels and pointed toes. The stiletto heel—engineered for drama—emerged, giving women (and Hollywood) the power to craft an entrance and silhouette that couldn’t be ignored. Suddenly, a shoe could be innocent or wicked, understated or a weapon—it depended entirely on the wearer.
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Go-Go and Groove: The 1960s–70s – Space Age and Saturday Night
The Swinging Sixties said goodbye to demure lines and hello to go-go boots, Mod style, and chunky mid-height heels. White boots and geometric cut-outs led the way, thanks to designers like André Courrèges and the infectious beat of British youth culture.
The 1970s belonged to disco fever and boundary-breaking expression. Sky-high platforms strutted their stuff in clubs from London to New York. Drag queens, rock stars, and rebels of all kinds claimed space in dazzling, sometimes outlandish shoes—proving once and for all that heels were for everyone. Remember: a glittery dancing queen never counted the hours—or the blisters.
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Power Moves and Pop Queens: The 1980s–90s – Bold, Bright, and Blazing Trails
Think power suits and shoulder pads, colour blocking, and serious shoe drama. As women stormed boardrooms, the stiletto returned as a signal of unapologetic ambition. Enterprising designs emerged: sharp toes, glossy patents, and even playful slingbacks. Madonna, Princess Diana, and the supermodels’ “model-off-duty” style reigned supreme.
The 90s gave us minimalist mules, strappy sandals, and yes, “ugly” platforms—grunge and girl power alike. Heels became a marker of identity: a Spice Girl platform for one night, a no-nonsense pump for the next. The rules relaxed, but the possibilities grew.
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New Millennium Mavericks: The 2000s–Now – Breaking Every Rule
The last 25 years have seen more freedom and choice than the rest of heel history combined. Think shouting colour, sculptural heels, gender-fluid designs, and creative collabs between icons and indie labels. Louboutin made red soles a status symbol; Choo and Blahnik made luxury mainstream.
And—most importantly—the boundaries of who ‘gets’ to wear heels have shattered. Drag artists, grooms, trans femmes, and every style rebel can find shoes in any size, shape, or shade. At WIH, inclusivity is the new “classic.” Our clients are as likely to pair heels with tuxedos as with tulle, channeling both old-Hollywood glamour and streetwear chic.
Today’s style lovers are spoilt for choice: want a patent pump for presentations, a polka-dot Mary Jane for tea, or a neon platform for pride? The world is your runway, darling.
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Why Heel History Still Matters to Your Strut
Knowing the roots of your favourite silhouette or buckle adds depth to your style and confidence. When you slip into a pair of retro-inspired T-straps or choose a dramatic modern stiletto, you’re honouring a line of innovators and rebels—people who made the world notice each step.
- – **Curious about vintage fit and care?** Maribel’s VIP tuition includes tips for breaking in and styling shoes from any era.
- **Feeling stuck between styles?** Book a group class to test-drive different silhouettes and history-inspired moves.
- **Want in on the drama?** WIH is bursting with stories from clients of every generation (and identity!) who made ‘yesterday’s heels’ their own.
Your heels don’t just echo the past—they announce your presence, your hopes, and your right to take up space, exactly as you are.
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Finding Your Place (and Era) in the WIH Community
Which decade calls you: ‘20s Jazz Baby, ‘50s bombshell, ‘70s disco diva, or future icon? The best part of the journey is mixing eras to create a look that speaks to your unique story. Dress up, experiment, swap shoe stories and techniques—there are no rules at WIH, only encouragement.
Looking for guidance on how to walk, what to pair, and how to feel fabulous, regardless of era? Book a one-to-one or join a group workshop for expert, inclusive coaching that bridges past and present.
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Your confidence is timeless. Strut tall in your favourite pair, and know you’re part of a community where history is honoured and boundaries are made to be broken. Subscribe to The Heel Diaries for more cheeky insights, expert tips, and inspirational stories from WIH—because every stride writes a new chapter.