Choosing the right heels after 50 isn’t about abandoning style—it’s about embracing comfort without sacrificing elegance. As our feet change with age, so should our footwear choices. I’ve spent decades in the fashion industry, and I’m here to share which heels will keep you strutting confidently and which ones might leave you wincing in regret.
1. Block Heels: Your Feet’s New Best Friend
Oh, how I adore a good block heel! They distribute weight evenly across your foot instead of concentrating pressure on your poor toes and ball of foot.
The stability they offer means you won’t wobble around like you’re walking on stilts at your neighbor’s garden party. Trust me, your back will thank you profusely.
2. Kitten Heels: Purr-fectly Balanced Elevation
Whoever invented kitten heels deserves a lifetime achievement award! These dainty one-to-two-inch wonders give just enough lift without turning your arches into architectural disasters.
Where once I scoffed at their modest height, now I cherish how they let me dance at my niece’s wedding without needing foot massage therapy afterward.
3. Slingbacks With Cushioned Footbeds
Heavenly cushioning makes all the difference between grimacing through dinner and genuinely enjoying yourself! Modern slingbacks often come with memory foam insoles that remember your foot’s shape better than some people remember birthdays.
The adjustable back strap accommodates those midday swelling moments without cutting off circulation to your toes.
4. Wedges: Height Without The Hurt
Though wedges have gotten a bad fashion rap occasionally, I’ve found them to be absolute lifesavers for outdoor events. No more sinking into grass or wobbling across cobblestones!
The continuous sole provides crucial arch support that conventional heels simply cannot match. Plus, they pair beautifully with everything from maxi dresses to tailored pants.
5. Mary Janes With Adjustable Straps
Mary Janes aren’t just for schoolgirls anymore! The modern versions with adjustable straps accommodate those days when your feet decide they’re slightly larger than yesterday.
Having worn these to countless gallery openings, I can attest they’re perfect for when you need to stand for hours. The strap keeps your foot securely in place without painful toe-gripping.
6. Low-Height Pumps With Rounded Toes
Whoever declared that pointed toes were the only elegant option clearly never experienced bunion pain! Rounded toe pumps give your piggies room to breathe without looking matronly.
With just enough height to elongate the leg but not enough to torture your metatarsals, these classics have remained in my rotation for decades. They transition seamlessly from boardroom to dinner party.
7. Heeled Loafers: Business-Chic Comfort
Whoever thought to add a modest heel to the classic loafer deserves a fashion Nobel Prize! These beauties combine the polish of a heel with the comfort of your favorite flat.
The stacked heel provides stability while the loafer design keeps your foot secure. I’ve walked miles through airports in mine without a single complaint from my formerly fussy feet.
8. T-Strap Heels With Ankle Support
Having twisted my ankle more times than I care to admit in conventional pumps, discovering T-strap heels was like finding water in a fashion desert. The vertical strap provides crucial stability for those of us with wobbly ankles.
Though they take a moment longer to buckle, the extra support is worth every second. They’re particularly lovely with skirts that show off the elegant ankle detail.
9. Platform Pumps (With Modest Height)
Contrary to what you might think, a subtle platform can actually make heels more comfortable! The platform in front reduces the effective heel height, creating less strain on your arches.
While I avoid skyscraper versions, a modest 1/2-inch platform with a 2-inch heel creates the illusion of height without the punishment. They’ve become my secret weapon for evening events.
10. Needle-Thin Stilettos: Torture Devices Disguised As Shoes
Though I once pranced around in 4-inch stilettos like they were bedroom slippers, my feet now stage full-scale rebellions at the mere sight of these spindly torture instruments. The concentrated pressure on the ball of foot is excruciating!
After 50, these beauties belong in a display case, not on your feet. No outfit is worth the potential for falls or fractures.
11. Backless Mules With High Heels
High-heeled mules require constant toe-clenching to keep them from flying off mid-stride. This tension creates a ripple effect of pain through the entire foot, ankle, and eventually up to the knees.
Without back support, these treacherous beauties force your feet to work overtime. After wearing them to one wedding, I needed three days of recovery and a stern talking-to from my podiatrist!
12. Completely Flat Dress Shoes
Surprisingly, completely flat shoes can be just as problematic as too-high heels after 50! The total absence of heel height provides zero arch support, leading to plantar fasciitis and heel pain.
I learned this painful lesson after wearing ballet flats to an all-day conference. A modest heel actually distributes weight more naturally than these deceptively innocent-looking foot flatteners.
13. Strappy Sandals With Minimal Support
Those dainty strappy sandals with pencil-thin soles might look ethereal in magazine spreads, but they’re absolutely devilish to aging feet. Without proper cushioning, every step feels like walking on concrete in paper-thin socks.
The lack of support around the ankle and arch means your foot muscles must work overtime. I’ve retired mine after one too many evenings of foot cramps.
14. Plastic or PVC Transparent Heels
While these clear beauties might channel your inner Cinderella, they’re actually wicked stepmothers in disguise! Non-breathable plastic creates a sweaty sauna effect that’s both uncomfortable and potentially slippery.
Having once worn these to a summer garden party, I can confirm they fog up like bathroom mirrors. Plus, the rigid material offers zero flexibility for feet that need gentle accommodation.
15. Over-Embellished Evening Shoes
Those gloriously bejeweled statement shoes with crystals, feathers, and whatnot might look spectacular in photos, but they’re heavy! The added weight of extensive embellishments creates unexpected strain on aging joints.
After wearing my rhinestone-encrusted pair to a gala, my toes were numb for hours. Now I opt for elegant simplicity rather than carrying what feels like a chandelier on each foot.
16. Sky-High Platform Boots
Though these dramatic stompers might make you feel like a rock star, the combination of extreme height and weight creates a dangerous equation. The elevated platform severely reduces foot flexibility and ground feel.
Having twisted my ankle in these fashion statements at age 52, I’ve learned my balance isn’t what it once was. No amount of style is worth a fractured bone or ligament tear!