How To Pick The Right Shoes To Go With Your Pants

When Danielle moved from New York to LA, she began to expand her shoe collection—now that she didn’t have to walk anywhere, she could shop with reckless abandon. But more shoes led to more questions! Take, for example, her new Alexander Wang snakeskin pumps. They have an amazing ankle strap situation designed to show off. And the super chic grey suede Madewell booties: They’re perfect for dresses, but can you wear them with a skinny jean? What about a cropped pant?  Now that’s putting your best foot forward.

Photographer: Luke Wooden 
Hair and Makeup: Michelle Mungcal at Atelier Management 
Model: Stephanie at Photogenics



A slingback elongates the leg and balances the athletic attributes of a dressed up sweatpant so that it still feels feminine and polished. 

Sea Denim & Shearling Hooded Vest ($575) in Indigo; Tory Burch Florence Sweater ($250) in Camel Melange; Elizabeth and James Reed Sweatpants ($295, similar style here) in Black/Ivory; ShoeMint Karla Heels ($90) in Black.

Celeste d’Orsay Pumps ($350) in Pomegranate

Kurt Geiger London

Bond Pumps ($385) in Yellow Leather

Alice + Olivia

Dina High Heels ($295) in Amethyst

With louche, floor-grazing pants, height in the shoe is key. A wide leg or flare trouser needs at least 3 1/2 inches to balance the volume. Plus, it will give you legs for days. Stay away from anything with a pointed toe, as it fights with the hem, and stick to something slightly rounded.  

AllSaints Cammie Leather Jacket ($455) in Black; Iris & Ink The Pussybow Silk-Crepe Blouse ($125) in Off White; Joie Sitara Crepe Pants ($188) in Caviar; Manolo Blahnik Agatha Bicolor Leather Slides ($755) in Black White.


Jenni Kayne

Haircalf Mules ($625) in Black

Alexander Wang

Dina Mules ($575) in Buff

Jeffrey Campbell

Cassatt Pointed Toe Booties ($180) in Black Box

This touches on two points: how to navigate a pair of ankle boots that come up a few inches above the ankle, as well as what to do with those few extra inches of jean that hit below. Look for ankle boots that taper closely, so there isn't too much space between the boots and the jeans can scrunch over it.

Karen Walker Pennsylvania Jacket ($840) in Ecru; ATM Anthony Thomas Melillo Sweetheart Tank ($65) in Heather Grey; Citizens of Humanity Rocket Highrise Skinny Jeans ($198) in Au Natural; Hue Cotton Tissue Socks ($7) in Black; Tory Burch Lenny Booties ($395, 310.248.2612, similar style here) in Black. 


Ultimately, you always want your legs to appear as long as possible. A delicate heel, as opposed to a three to four inch heel, gives a quiet but elegant touch that elevates the look without overwhelming the pant.  

Zara Pin Stripe Coat ($239) in Navy Blue; Bec & Bridge Celestial Knit Tank ($240) in Ink; Alexander Wang Cropped Tuxedo Trousers ($575) in Geyser; Reed Krakoff Suede & Metallic Leather Slingback Pumps ($750) in Navy.

Banana Republic

Giah Pumps ($98) in Claret 

Tory Burch

Noelle Pumps ($350) in Electric Eel 

Salvatore Ferragamo

Rietta D’Orsay Pumps ($575) in Nero

Some people just need to be strapped into their shoes—me being one of them—but what to do with it? Try a cropped skinny that hits a few inches above the strap, but make sure it's fitted throughout so that the lines of the hem are streamlined with the ankle strap. It’s good to leave a little space in between so you can really show them off! 

M. Patmos Bomber Jacket ($995) in Olive; T by Alexander Wang Distressed Merino Blend Knit Pullover ($275) in Forest; J Brand Anja Leather Pants ($1,076) in Black; Paul Andrew Bouchra Heels ($965) in Black/White.

Alexander Wang

Lovisa High-Heeled Pumps ($485) in Leopard

Loeffler Randall

Alba Demi Platform Pumps ($395) in Taupe 

There’s actually a lot of shoes that can be worn with this more fashion-forward style, reminiscent of ‘80s Japanese fashion. Since cropped wide leg pants are opiate of the of the street style masses lately, we suggest just going with the flow and letting the look be more masculine. Oxfords with a chunky platform balance the wide leg while adding height, preventing the pants from making you look bottom heavy.  

J Brand Itani Sweater ($575) in Oatmeal Heater; ASOS Boyfriend Shirt with Wordy Wing Placement Print ($37) in Multi; Karen Walker Crisscross Pants ($650, similar style here) in Chestnut; Hue Cotton Tissue Socks ($7) in Black; Loeffler Randall Calla Platform Creepers ($350) in Black Dot Haircalf. 

Alejandro Ingelmo

Kennedy Platform Loafers ($575) in Oro

Surface to Air

Flatbush Creepers ($440) in Silver