Photo:
@chrissyford
On Chrissy Rutherford: BY FAR bag
Leather pants and black boots are always a winning combo.
BY FAR
Este 25mm Square Toe Ankle Boots
$484
Photo:
@missenocha
On Enocha Tellus: Zara boots
It doesn’t get chicer than a textured sweaterdress and knee-high heeled boots.
Staud
Cami Boot Tan Suede
$550
Photo:
@alyssainthecity
On Alyssa Coscarelli: Staud Large Moon Bag
Little block-heel boots make tailored trousers look even more polished.
Sam Edelman
Irie Bootie
Photo:
@lefevrediary
On Amy Lefévre: Schutz boots
The only thing that can make a jumpsuit cooler is a pair of heeled boots.
Tony Bianco
Fantasy Butter Nappa 8cm Calf Boots
$360
Photo:
@champagnemani
On Imani Randolph: For Love & Lemons dress
Hello, date-night look!
Zara
Zippered Heeled Ankle Boots
$90
Photo:
@aimeesong
On Aimee Song: Chloé bag
When in doubt, go monochrome.
Free People
Rocky Slouch Boots
$298
Photo:
@bettinalooney
On Bettina Looney: Bottega Veneta The Pouch Large Clutch ($2700)
Make your favorite heels work for winter by adding opaque tights.
Jimmy Choo
Bing Crystal Embellished Patent Mule
$995
Photo:
@slipintostyle
On Ellie: Stand Studio coat; Saks Potts pants; Charles & Keith shoes, Le Specs The Last Lolita Sunglasses ($119)
Mixing prints and bold colors gets taken up a notch with the addition of heeled ankle boots.
Vince Camuto
Quindele Pointed Toe Bootie
$159
Photo:
@deborabrosa
On Débora Rosa: Mango outfit
Make a Canadian tuxedo even cooler with black heeled ankle boots (and maybe throw a big coat on top when heading out).
Mango
Block Ankle Boots With Square Toe
$70
Photo:
@anoukyve
On Anouk Yve: Jimmy Choo boots; Little Lifner bag
Dress up your favorite coat and thick scarf with a pair of knee-high heeled boots.
Vicenza
Friday Fever Heel Boots
$248
Photo:
@ada_oguntodu
A cool outfit gets even cooler with sleek heeled ankle boots.
Staud
Wally Ankle Boots
$395
Photo:
@emilisindlev
The best way to add a pop of color to an otherwise neutral outfit? Bright-hued heels.
Jeffrey Campbell
Estella Pointed Toe Slingback Pump
$145
Photo:
@natashandlovu
On Natasha Ndlovu: Alexander McQueen coat; Bottega Veneta Jodie Mini Bag ($1720)
Your favorite sweaterdress was made to be paired with pumps.
Sam Edelman
Bianka Slingback Pump
$140
Photo:
@dolcecurvy
The classic combination of a turtleneck sweater, trousers, and a black coat suddenly feels modern when styled with heeled black ankle boots.
Tory Burch
Double T Ankle Boot
$478
Photo:
@venswifestyle
On Renia Jaz: Bottega Veneta The Chain Pouch ($3600)
Camel always looks expensive—even more so when paired with neutral-colored pumps.
Aeyde
Melia Leather Point-Toe Pumps
$395
Photo:
@symphonyofsilk
On Lorna: Polène bag
Give your favorite blazer-and-skinny-jeans outfit a fun twist with heeled boots (bonus points if they’re snake print).
Reformation
Remy Knee Boot
$478
Photo:
@smythsisters
On Marianne: Levi’s jeans
The perfect dinner-at-home look includes a white button-down, black jeans, heeled boots, and a chunky scarf.
Reformation
Roberta Ankle Boot
$348
Photo:
@babba
Colored coats are always fun, and heeled black ankle boots just make them feel a touch more polished.
Madewell
The Dimes Kitten-Heel Boot
$198
Photo:
@amandasorensonn
White heeled boots were made to be worn with plaid coats.
Mango
Round-Toe Leather Boots
$250
Photo:
@femmeblk
On Lydia Tsegay: Polène bag; Zara T-shirt; Sentaler coat
Strappy heels with an all-white look are as aspirational as it gets.
Stuart Weitzman
Nudistcurve 100 Smooth Leather Sandal
$475
Photo:
@polliani
On Janka Polliani: Gucci bag and Off-White Tights ($120)
This feels like a modern-day Blair Waldorf outfit—in a good way.
Charles & Keith
Black Gabine Patent Leather Mules
$83
Photo:
@ileniatoma_
On Ilenia Toma: Gucci GG Marmont Mini Bag ($950)
Note to self: Invest in tights.
Steve Madden
Lizah Knee High Boot
$100
Photo:
@greceghanem
On Grece Ghanem: Zara blazer
A simple blazer and jeans are suddenly an outfit with the addition of unique heels.
Manolo Blahnik
Hangisimu 70 Embellished Satin Mules
$1095
Classic.
Photo:
@styleheroine
On Evangelie Smyrniotaki: Woolrich jacket
Slightly baggy jeans feel balanced with a lift from sleek pumps.
Zara
High Heeled Shoes
$50