I'm one of Big Stiletto's most loyal fans. If I'm not in a training sneaker, you won't find me in flat footwear, and until recently, a chunkier heel couldn't be sourced from my closet. That is, until recently. In the last few seasons, brands like Tory Burch, Khaite, and The Row sparked an interest in block heels, developing fresh takes on the dated shoe silhouette that made me rethink my strict loyalty to skinny and often unstable lifters. Their heels were thicker and heartier and, as such, quite approachable, even at high heights. At the same time, they were just as sleek as any stiletto I'd ever seen, not to mention fresher and different from my usual rotation. Immediately, I began my search for the perfect pair.
Obviously, there are the classic Tabi pumps, which come in a variety of silhouettes, many with a thicker, cylindrical heel. But if you're not in the market for such a divisive toe shape, don't fret. Most of the below options are far more approachable in appearance, not to mention price, with a mix of high and low prices at your fingertips. Think Massimo Dutti, Zara, and Jeffrey Campbell mixed in with Gucci, Prada, and Celine.
What each of these shoes shares is a '90s look with a twinge of old Prada—the latter is more noticeable in some pairs than others—and an overall cool factor that deserves to be shown off. Wear them with tights and a knee-length wool or leather skirt or dress in the wintertime. In the summer, opt for something lighter, like linen or silk, but in a similar silhouette. You can even style them with fitted trousers for a sophisticated ensemble that still feels youthful and chic. The options are, as they say, endless.
Scroll down to find your perfect pair. I know I'll be busy finding mine.
ZARA
Square Toe Leather Mules
Once I saw that Zara was getting in on this trend, I knew it was about to blow up.
Maison Margiela
Tabi Heels
These are a piece of fashion legend for a reason. Not only are they famously comfy, but they also signify that you have taste and know what you're talking about.
Tory Burch
Sculpted Peep-Toe Pump
These Tory Burch peep-toe pumps put a spell on me. They look to have been molded by the gods.
Massimo Dutti
Heeled Shoes With Rounded Toe
You bet these are already in my cart.
MANGO
Patent Leather-Effect Heeled Shoes
KHAITE
Cedar Glossed-Leather Pumps
Peep toes are another major comeback trend in 2025. This pair checks off two buzzy buys in one.
MANGO
Heeled Leather Loafers With Pleat Detail
Please style these with fun socks or tights. I'm begging.
THE ROW
Prudens Leather Pumps
Every season, The Row puts out a show that instantly sparks something inside of me. This is that pair right now.
ZARA
Heeled Pump With Strap
The T-strap makes this pair even more tempting, not to mention the $70 price tag.
These are selling scarily fast.
GUCCI
Lady Horsebit-Embellished Patent-Leather Slingback Pumps
If you love a horsebit Gucci shoe but aren't a loafer person (I feel you), go for this gorgeous block-heel slingback instead.
SARTO by Franco Sarto
Diona Ankle Strap Pointed Toe Pump
These feel extra '90s to me.
3.1 Phillip Lim
Nadia Heeled Ballerina Pumps
You can tell just from looking at these that they're comfy.
CELINE
Celine Lily Triomphe Pump in Patent Calfskin
Jeffrey Campbell
Bourdin Mary Jane Pump
These are tall, but the heel makes them so much less intimidating.
Prada
Patent Leather Slingback Pumps
You're gonna feel like Dorothy in these red slippers.
You know who loved a pop of leopard print? Carolyn Bessette-Kennedy. Enough said.
Nordstrom
Paola Ankle Strap Pointed Toe Pump
Just order them. You know you want to.
MANOLO BLAHNIK
Okkatopla 50 Suede Pumps
A great pair of classic Manolos will never be an irresponsible purchase.
AEYDE
Magda Patent-Leather Pumps
The kind of heel you can walk in for hours.
Prada
Brushed Leather Pumps
I'm going to Milan in a few weeks and just might have to come home with these.
Jeffrey Campbell
Hints-2 Suede Square Toe Pump
PARIS TEXAS
Belle Snake-Effect Leather Slingback Pumps
And always to snakeskin. Always.
