Claire’s Pick of the Best Stiletto Heels

A good stiletto earns its height through construction, not just the number on the box. The heel itself should sit directly under the centre of the foot, not set back towards the arch, because that alignment is what keeps a four inch heel walkable rather than a wobble waiting to happen. Look at the shank, the piece of steel or rigid material running through the sole, because a stiletto without proper internal support will flex and eventually snap at the arch, however good the leather looks. The toe shape matters more than people admit too. A pointed or almond toe elongates the leg in a way a rounded one simply cannot, and a slightly tapered vamp, the front part of the shoe, does more for the line of an outfit than any amount of embellishment.

Leather uppers, whether smooth calf or a soft suede, move with the foot and soften with wear, while stiff synthetics tend to rub and crease unattractively at the point where the foot bends.

A well made stiletto should feel snug at the heel, with no slipping, and have enough room across the toes that the foot isn’t forced into an unnatural point.

Styling one is less complicated than most people make it. A stiletto with a tailored trouser, cropped at the ankle, gives a sharper line than any flat ever could, and the same shoe under a straight leg jean instantly dresses down a smart top for evening.

With a midi skirt or a slip dress it does the heavy lifting on its own, so keep the rest of the styling clean rather than piling on competing statement pieces. For daytime, a block colour that matches or nearly matches the skin tone tends to look more expensive than anything patterned, since it keeps the leg line unbroken.

Occasion wise, this is the shoe for anything that asks for a bit of formality, from evening events and dinners to interviews where a low heel would undersell the outfit. It is not the shoe for long stretches of walking or cobbled streets, and a stylist worth listening to will always suggest keeping a flatter pair nearby for the transition between venue and taxi, rather than pretending endurance is part of the appeal.

Top Picks

MADISON’S PICK STICKALZ – CAR GRAPHICS & VEHICLE DECALSHigh Heel Stiletto Shoes Woman Bag Purse Female Fashion Beauty Wall Sticker Decal Vinyl Mural Decor Art L2330 - 15x24 inches / Purple

$44.99 STICKALZ – CAR GRAPHICS & VEHICLE DECALS

TAYLOR’S PICK IFCHICJIMMY CHOO 'Love' Satin Pointed Stiletto Heel Pumps - EU

$850.00 $722.50 IFCHIC

CARL’S PICK FLORALKINIStar Rhinestone-Embellished Ankle Wrap Around Stiletto Heel Sandals - US 6/EU 37 / Black

$82.99 FLORALKINI

JASMINE’S PICK W CONCEPT (US)High Heel Stiletto Shoes [Black]

$66.00 W CONCEPT (US)

HARPER’S PICK W CONCEPT (US)3cm Ribbon Stiletto Kitten heel (CW0079BUR)

$107.00 W CONCEPT (US)

CHICSEW TRADING CO., LIMITEDWomen's Pointed Toe High Heel Stiletto Pumps Wedding Dress Shoes $79.99 CHICSEW TRADING CO., LIMITED

TINACUSTOM.COMTinaCus Genuine Leather Women's Handmade Pointed Toe Spikes-Stiletto Supper High Heel Side Zip Up Sexy - US5/CN34/EU35/UK3/Foot Length-22cm / white $113.50 TINACUSTOM.COM

STICKALZ – CAR GRAPHICS & VEHICLE DECALSHigh Heel Stiletto Shoes Woman Bag Purse Female Fashion Beauty Wall Sticker Decal Vinyl Mural Decor Art L2330 - 46x75 / Burgundy $99.99 STICKALZ – CAR GRAPHICS & VEHICLE DECALS

SHIEKHWomen Stiletto Heel Bootie Serenity-Pinkdisco Boots 7.5 Serenity $49.99 SHIEKH

SHIEKHWomen Edit Stiletto Heel Bootie Black High Heels 7.5 Black $64.99 SHIEKH

DRESTIGE USWomen's Shoes Steve Madden Open sandal with stiletto heel, clasp with buckle. $206.10 DRESTIGE US

THE LUXURY CLOSETMoschino Gold Leather Stiletto High Heel Sandals $123.00 THE LUXURY CLOSET

STICKALZ – CAR GRAPHICS & VEHICLE DECALSHigh Heel Stiletto Shoes Woman Bag Purse Female Fashion Beauty Wall Sticker Decal Vinyl Mural Decor Art L2330 - 15x24 inches / Purple $44.99 STICKALZ – CAR GRAPHICS & VEHICLE DECALS

GODDIVAGoddiva Diamante Bow High Stiletto Heel $66.00 GODDIVA

TINACUSTOM.COMTinaCus Genuine Leather Women's Handmade Pointed Toe Spikes-Stiletto Supper High Heel Side Zip - US4.5/CN33/EU34/UK2-2.5/Foot Length-21.5cm / black $113.50 TINACUSTOM.COM

CHICSEW TRADING CO., LIMITEDDiamante Heels Wrap Around Strap Fantasy Rhinestone Sparkly Stiletto Heel Sandals - Sliver / US9 $89.99 CHICSEW TRADING CO., LIMITED

FLORALKINICroc Print Wide Fit Pointed Toe Stiletto Heel Knee High Boots-White/Orange/Red/Green/Black/Cyan/Brown/Lime - US 12/EU 43 / Orange $95.99 FLORALKINI

FLORALKINIStar Rhinestone-Embellished Ankle Wrap Around Stiletto Heel Sandals - US 6/EU 37 / Black $82.99 FLORALKINI

TINACUSTOM.COMTinaCus Genuine Leather Women's Handmade Pointed Toe Spikes-Stiletto Supper High Heel Side Zip Up - US7.5/CN38/EU38/UK5.5/Foot Length-24cm / orange $113.50 TINACUSTOM.COM

FLORALKINIFaux Leather Scrunched Slouch Mid-Calf Pointed Toe Stiletto Heel Boots - US 4/EU 35 / Black $84.99 FLORALKINI

EGO (US & CA)Cecil Square Toe Stiletto Heel Knee High Long Boot In Burgundy Faux Leather, Women's Size US $54.00 EGO (US & CA)

CHICSEW TRADING CO., LIMITEDPearl Slingback Heels for Women, Pointed Closed Toe Slip On Heeled Sandals Stiletto Heel Evening Bridal Shoes for Wedding $79.99 CHICSEW TRADING CO., LIMITED

W CONCEPT (US)High Heel Stiletto Shoes [Black] $66.00 W CONCEPT (US)

W CONCEPT (US)3cm Ribbon Stiletto Kitten heel (CW0079BUR) $107.00 W CONCEPT (US)

W CONCEPT (US)1057 Loce Gold Square Stiletto Heel $157.00 W CONCEPT (US)

EGO (US & CA)Next-Diva Diamante Clear Perspex Strap Stiletto Heel Mule In Black Satin, Women's Size US $25.00 EGO (US & CA)

−80%

NINA SHOESWomens Dorcas Steel Metallic Textured Block-Heel Stiletto Platform Dress Sandal$99.95 $19.99 NINA SHOES

−25%

IFCHICGIANVITO ROSSI Orchid Fabric Stiletto Heel Sandals - EU$800.00 $600.00 IFCHIC

−15%

IFCHICJIMMY CHOO 'Love' Satin Pointed Stiletto Heel Pumps - EU$850.00 $722.50 IFCHIC

−20%

IFCHICJIMMY CHOO Azia Patent Leather Square Toe Stiletto Heel Sandals - EU$950.00 $760.00 IFCHIC