25 Pointed-Toe Shoes That Will Keep Your Style on Point

The silhouette is classic for a reason.

pointed toe shoes

Charles & Keith

The revival of ‘90s fashion over the past several years has brought with it a strong appreciation of shoes with chunky soles, minimalist straps, and, quite famously, square toes. But with all due respect to the angular silhouette, it's pointed-toe styles that continue to have the most universal and timeless appeal.

Seen across flats, boots, and heels in the current market, pointed-toe shoes tend to remain popular despite fashion’s other cycling trends. This is thanks to the shape’s ability to lengthen the appearance of the legs, whether it's a subtle almond or sharp spike on the shoe. Even extra-long trousers that touch the floor look intentional and chic with a tiny triangular peak of a shoe from the hemline. Meanwhile, skirts and dresses of all lengths needn’t be styled with a heel when a pointed-toe flat can create the look of long legs, without the challenge of balancing on stilettos.

Ahead, explore a variety of pointed-toe shoes that are bold and exciting, yet timeless in silhouette.

Tibi Caden Stretch Boots
Tibi Caden Stretch Boots $575.00

Not the biggest fan of stilettos? A kitten heel with a pointed toe can sneakily make anyone look five inches taller.

Schutz Mikki Up Boot
Schutz Mikki Up Boot $238.00

These tall, high-heeled boots will be your midi dresses’ best friend this winter.

Rothy's The Point
Rothys The Point $145.00

Rothys climate-conscious flats are praised for their comfort, and this shade of red is quite striking, no?

By Dose Jasmine Two-Strap 100mm Mule
By Dose Jasmine Two-Strap 100mm Mule $353.00

Even with a barely there, sparkly strap, the pointed toes of these sandals are a statement-making touch.

Mango Slingback leather shoes
Mango Slingback Leather Shoes $120.00 $80.00

Pointed-toe mules—especially in a vibrant green—are for work and play.

Wally Boot Saddle Croc Embossed
Staud Wally Boot Saddle Croc Embossed $550.00

The rich texture of these boots will give any outfit some oomph.

Jimmy Choo Love 85mm Leather Pumps
Jimmy Choo Love 85mm Leather Pumps $695.00

No pointed-toe round-up would be complete without the pump, the most timeless of all heel styles.

Peche Benson
Pêche Benson $92.00

For everyday comfort and chunky-shoe appeal, these Pêche loafers are it.

Amina Muaddi Begum 95mm Crystal-Embellished Pumps
Amina Muaddi Begum 95mm Crystal-Embellished Pumps $1,220.00

Oh-so-far from your average pair of pumps.

Prada Triangle Logo Pointed Toe Slingback Pump
Prada Triangle Logo Pointed Toe Slingback Pump $950.00

Prada brings a dose of sportiness to its kitten-heel pumps.

Fabienne Pile
Flattered Fabienne Pile $84.00

A fuzzy take on the classic black kitten heel.

Dallas Suede Knee Boots
Khaite Dallas Suede Knee Boots $1,380.00

A white, kitten heel Western boot is a fresh, modern take on a traditional pointed-toe silhouette.

Louise Et Cie Jadran Pointed Toe Bootie
Louise Et Cie Jadran Pointed Toe Bootie $96.00

You’re new go-to black booties have a touch of velvet and a flared heel.

Chelsea Paris Dexter Pump
Chelsea Paris Dexter Pump $285.00

Why not get playful with ankle-wrapping straps and tassels?

Keeyahri Zerina $1,199.00

We love the sleek, tall shaft and flawless leather of these Keeyahri boots, but the structural heel is the star of the show.

Elleme Chouchou Ballerina Pointed Toe Flats
Elleme Chouchou Ballerina Pointed Toe Flats $405.00

For a subtle dose of quirkiness, we all about the scrunchie details on these flats.

Jacolina Heel
Vince Camuto Jacolina Heel $110.00

Vince Camuto's pastel mint heel will be your go-to for spring.

Alaia Pointy Toe Clog
Alaïa Pointy Toe Clog $1,170.00

Clogs have made their return, from the runway to e-commerce sites everywhere. And best yet, now they have a tapered toe.

Intentionally Blank West Clouds
Intentionally Blank West Clouds $225.00

We love the adjustability of a lace-up option.

Brother Vellies Olivia Pump
Brother Vellies Olivia Pump $795.00

Both the pointed toe plus delicate foot-to-ankle jewelry create a lengthening effect.

Charles and Keith Croc-Effect Bow-Tie Mules
Charles & Keith Croc-Effect Bow-Tie Mules $49.00

Whenever spring makes its return, we’ll be wearing these mules to welcome it.

Tory Burch Jessa Pointed Toe Loafer
Tory Burch Jessa Pointed Toe Loafer $348.00

There’s an extra bit of drama in the very sharp toe tip of these Tory Burch loafers.

Fred Salvador Ruthie Ankle Boot
Freda Salvador Ruthie Ankle Boot $495.00

The snake skin is eye-catching, but also neutral enough to go with any trouser or denim wash.

Marion Parke Must Have Flats
Marion Parke Must Have Flats $475.00

It’s simply a fact: Black, pointed-toe flats are one of the hardest working shoes in a wardrobe.

Magaux The Chelsea Boot
Margaux The Chelsea Boot $328.00

The timeless Chelsea gets an update with an elongated silhouette.

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