You know what? I didn’t expect to like Cuban heels this much. I thought they’d feel loud or costume-y. But I wore three pairs, in real life, for real stuff. Work. A wedding. A gig. The whole shebang.
If you want the blow-by-blow version—including blister reports and all—here’s the full day-by-day diary I kept during that month of wear-testing read it here.
So, here’s what happened.
Why Cuban Heels, Anyway?
Cuban heels give a small lift. Not stiletto-tall. Not flat. Most are around 1.5 to 2 inches. They look a bit 70s rock, a bit cowboy, a bit dance floor. Think clean lines, solid block heel, and a little drama. Not too much—just enough. For a glimpse of authentic Cuban style that inspired these heels, take a quick scroll through the street-style photos on Lovely Cuba — the color and energy translate straight into footwear.
Also, yes, the click-clack on tile sounds cool. Until you’re in a quiet hallway.
If you’re curious about what technically makes a heel “Cuban”—from the blocky silhouette to the way it supports your weight—the folks at MasterClass break it down in detail right here.
The Three Pairs I Actually Wore
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Saint Laurent Wyatt 40 (black suede, 40mm heel): I wore these to a friend’s wedding and two long office days. Pricey. Sharp. Very “I have my life together,” even when I don’t.
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ASOS Design Cuban Heel Chelsea Boots (black leather): Budget buy for daily wear. I used these on city commutes and a concert. They’re lighter and less fussy. Not as crisp as the Saint Laurents, but they held up.
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Capezio 2" Character Shoes (Cuban heel): I used these for a salsa class and a small theater run. Stable heel. Good for turns. Your ankles feel locked in, in a good way.
The Good Stuff
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The height boost: I’m 5'6". These make me feel 5'7-ish. It shows in photos. My stance looks longer. Clothes hang better.
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Balance and stance: The heel tilts you just a bit forward. My walk felt steady. Not tottery. More “I own this room.”
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Style play: With cropped black jeans? Chef’s kiss. With a suit? Sharp. With a midi skirt and tights? Kicks up the whole look. Pair any of those combos with a chunky chain around your neck—here’s my no-fluff review of one in solid gold—and the ensemble suddenly feels curated.
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The vibe: They whisper rock star. Not shout. If Harry Styles shows up in your brain, yeah—same.
And if you want proof that this silhouette has been stealing spotlights for decades—think Beatles boots, Saturday Night Fever disco floors, even modern political campaigns—there’s a fun timeline in The Guardian here.
The Not-So-Fun Bits
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Break-in pain is real: The Saint Laurents pinched my left pinky toe for the first week. I used thin wool socks and a shoe stretcher overnight. Better after 3 wears.
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Slippery soles: Leather soles on tile felt slick. I added thin rubber taps (my cobbler calls them “topy”). Problem solved.
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Heel caps wear fast: Street use chewed up the heel caps in 4 months. My cobbler replaced them. Cheap fix, but still a trip.
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Noise: Clicks on tile are fun until you’re in a library. I tiptoed around like a cartoon burglar.
Fit and Sizing (Learned the Hard Way)
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If you have wide feet, try half a size up in pointed styles. Cuban heels often run narrow at the toes.
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Heel slip is normal at first. If it keeps rubbing, add a small heel grip.
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If you’ll stand all day, look for a padded insole and a firm heel counter (that’s the stiff bit at the back).
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Suede feels softer right away. Polished leather lasts longer.
How I Styled Them (and Didn’t)
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Best hits:
- Black jeans, white tee, leather jacket. Finish the look with a slimmer, feminine-cut Cuban link chain (I tested one and shared the truth right here).
- Tailored trousers, thin knit, long coat.
- Midi skirt, tights, fitted blazer.
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Misses:
- Super skinny jeans that bunch at the ankle. The heel looked huge.
- Baggy sweats. It gave “I got dressed in the dark.”
Tip: Hem your pants so they just kiss the top of the boot. Clean lines matter here.
Work, Wedding, Dance Floor
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Office days: The ASOS pair handled 7,000-step days. By 3 p.m., I felt a little calf burn. Not bad, just present.
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Wedding: The Saint Laurents looked amazing with a simple black suit. I stood for hours. My feet survived, but I switched to gel insoles after the ceremony. Worth it.
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Salsa class: The Capezios made turns easy. The heel gave me an anchor. My teacher said my posture looked stronger. I’ll take the win.
Care That Saved Me
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Add rubber taps to the soles early. It’s cheap and helps grip.
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Brush suede after rain. Don’t skip this. Water marks move fast.
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Swap heel caps when they wear down. Don’t wait till metal shows.
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Keep cedar shoe trees in them. They keep shape and stop smells. Not glam, but hey.
Small Things I Didn’t Expect
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People notice. “Did you get taller?” came up three times in a week.
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Stairs feel different. You place your foot with more care.
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They make you stand straighter. Or maybe I was just trying to look cool.
Speaking of getting noticed, the extra inch of height and the built-in swagger turned out to be a surprisingly good ice-breaker when I dipped back into the dating pool; if you want to see whether footwear-induced confidence can translate into real-world matches, swing by Fish4Hoes—their location-based matching system quickly pairs you with nearby singles who appreciate bold style, so you can put that new swagger to good use. If you happen to be cruising through Oklahoma and prefer a guaranteed, sophisticated night out where your sharp boots won’t go unnoticed, consider meeting one of the local professionals listed at Claremore escorts for a curated companion experience—the profiles there let you choose someone who matches your vibe and can elevate an evening from ordinary to unforgettable.
And if you’re considering going full Havana, the headwear angle is worth a look—my month with a Cuban hat proved that a brim can be your best friend when the sun’s up and the salsa beats are on.
Who Should Try Them?
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If you like a bit of flair without going full runway.
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If you want some height but hate thin heels.
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If you love 70s music, Western boots, or theater shoes. This sits right in that sweet spot.
If you have knee pain or very flat feet, try a lower heel (around 30–35mm) and add arch support. Your body will thank you.
Final Take
Cuban heels aren’t loud shoes. They’re quiet confidence with a little rhythm. My Saint Laurent pair is for shine. My ASOS pair is for daily life. My Capezios are for the stage and studio. I had blisters at first. I also had better photos, better posture, and a better mood.
Would I wear them again? I already am. And honestly, that soft click on the sidewalk? It still makes me smile.