25 Outfits You'd Never Think to Wear With Heels — but Totally Should

There are pieces in your closet you'd never expect to wear with heels. When you bought those slouchy boyfriend jeans or that live-in graphic tee, you probably imagined rocking them with platform sneakers and a moto jacket. But when you slip into your stilettos and style the unexpected, well, that's what gets you head turns. Plus, it lends your wardrobe versatility — and there's nothing better than learning how to show off your staples in new ways. Read on for 25 unique looks that don't obviously belong with your pumps and platforms but work ridiculously well with them anyway.

01

A T-Shirt and Culottes

02

A Slip Dress and Jeans

03

Boyfriend Jeans and a Tunic

04

A Midi Skirt and Tee

05

A White Tee and Casual Army Jacket

06

A Trench Coat and Your Umbrella on a Rainy Day

08

Boyfriend Jeans and a Satin Tank

09

A Cozy Turtleneck Sweater

10

A Neck Scarf and a Tied-Up Flannel Shirt

11

Distressed Denim Shorts and a Bell-Sleeved Top

12

A Printed Silk Top, a Blazer, and Frayed Jeans

13

A Caftan You Could Easily Wear Over Your Swimsuit

15

A Silk Tank Over a Pajama Top and Black Skinny Jeans

16

A Long Chiffon Maxi and Bomber Jacket

17

A Bodysuit and Levi's

18

A Breezy Dress That Could Work Just as Well on the Beach

19

An Open Vest Over a Loose Printed Shirt

20

Belted Denim Culottes and a Turtleneck

22

An Oversize Cape Coat

23

A Thick Coatigan and Distressed Denim

24

Flared Pants and Lots of Layers Up Top

25

An Oversize Sleep Shirt and Jeans