Honestly, I remember when people laughed at the idea of a pop star designing footwear. It was 2005. Everyone thought it was a gimmick. But here we are in 2026, and my Jessica Simpson black high heels are still the most reliable things I own.
You've probably seen the headlines about her empire hitting $1 billion in sales and then the whole drama where she had to buy her own name back from Sequential Brands. It’s a lot. But through all the business chaos, the shoes stayed... surprisingly good?
I’m not saying they’re Manolos. They aren't. But if you need to stand at a wedding for six hours without wanting to saw your feet off, these are usually the answer.
The "Comfort" Secret Nobody Admits
There is this weird elitism in fashion. People assume if a shoe costs $79 at a department store, it must be a torture device.
Actually, the Jessica Simpson line uses a specific "Feather Touch" memory foam. I’ve worn the Jittale Stiletto—it’s a classic black pump—and it has this squishy layer that most luxury brands skip because they care more about the silhouette than your actual arches.
Why Black Heels specifically?
Black is the workhorse. You can get them in:
- Patent leather (the glossy stuff)
- Suede (looks expensive, nightmare in the rain)
- Matte faux-leather (the everyday hero)
I once wore a pair of the Adonia platform sandals to a charity gala. They have this massive 5-inch heel, which sounds like a death wish. But because the platform is nearly 2 inches thick, the actual pitch of your foot is barely anything. It’s basically a wedge in disguise.
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What Most People Get Wrong About Sizing
Sizing is where things get dicey. If you read the reviews on Zappos or DSW, you’ll see a war zone.
One person says they run huge. The next says they’re "designed for dolls."
Here is the reality: the pointed-toe pumps like the Prizma or the Cassanip run narrow. If you have even a slightly wide foot, you have to size up half a step. Otherwise, you’re looking at some serious toe-pinching by hour three.
I’ve found that the open-toe styles are much more "true to size." I’m a 7.5, and in her platform sandals, the 7.5 fits like a glove. In the stilettos? I’m an 8. Every single time.
The 2026 Trend: Why We're Going Back to Platforms
Fashion is cyclical, right? We spent a few years doing those tiny "kitten heels" that looked like something my grandma wore to church.
Now, everyone wants height again.
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The "Brat" aesthetic and the Y2K resurgence have made the Macee Platform or the Jixte sandals massive again. There’s something about a chunky black heel that just works with baggy jeans. It’s that "early 2000s Jessica" look—short hemline, huge shoes.
Styling them without looking like a throwback
Don't do the denim-on-denim thing unless you're ironic about it. Instead, try these:
- Black patent pumps with sheer black tights and a mini skirt. Very "French girl" chic.
- Chunky platforms with wide-leg trousers. The shoes give you height so the pants don't drag on the floor, but you can actually walk to the subway.
- Strappy stilettos with an oversized blazer. It balances out the "sexy" vibe with something more structured.
Is the Quality Actually There?
I’ll be real: these aren't "forever" shoes. If you wear them every day on city concrete, the heel tips will wear down in a season.
But for the price? It's hard to complain. You’re getting real suede in many cases, or high-quality synthetics that don't look like plastic.
I’ve had a pair of her black d'Orsay pumps for four years. I’ve had the heel taps replaced once at a cobbler for ten bucks, and they still look brand new.
Compare that to some "fast fashion" brands where the actual structure of the shoe starts to wobble after three wears. Jessica’s shoes feel solid. They don't have that "creaky" sound when you walk, which is my biggest pet peeve.
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How to Spot the Best Deals
Never pay full price.
Seriously.
Between Nordstrom Rack, 6pm, and the seasonal sales on her actual website, you can almost always find Jessica Simpson black high heels for under $60. I’ve seen the Calie pumps go as low as $35.
At that price point, you can afford to have a "backup" pair in the trunk of your car.
Actionable Insights for your next purchase:
- Check the Pitch: If the heel is over 4 inches, make sure there is at least a half-inch platform. Your lower back will thank you tomorrow.
- The "Pinch" Test: If you're buying pointed toes, go up half a size. Don't let your ego tell you you're still a 7 if the shoe is a 7.5.
- Material Matters: If you want them to last, stick to the matte leathers or suedes. Patent leather shows scuffs that are impossible to buff out once they’re deep.
- Inspect the Heel Tap: Before you wear them out, tap the heel on a hard floor. If it sounds "hollow" or like cheap plastic, take them to a cobbler for a rubber tip immediately. It’ll make them 10x more comfortable.