Pick The Right Shoes Every Time With Our Foolproof Guide

There are lots of potentially tricky silhouettes and unconventional hemlines on the horizon for fall—culottes and full skirts, we’re looking at you—all of which beg the question: what shoes should I wear with that? Luckily, we’ve got the answer!

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    From cropped jeans and prim pumps to leather leggings and printed ankle booties, we’re playing matchmaker and found a slew of perfect sole mates for today’s slideshow.

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    PHOTO: Stockholm Street Style

    Cuffed Jeans + Nude Sandals

    Roll the cuff of slim (but not skinny!) jeans to hit at or just above the ankle strap of the heels to create a sleek, elongating line.

     

    Get The Look:
    Frame Denim Le Garcon Slouch Jeans ($199) in Berkley Square; Chloe Two Tone Quarter Strap Sandals ($595) in Brick/Beige.

     

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    PHOTO: http://www.fashionvibe.net

    Bright Full Skirt + Open Back Flats

    Full skirts can go fancy quite fast, so offset their party-time vibe by grounding the look with a pointed-toe flat.

     

    Get The Look:
    Topshop Burnout Floral Midi Skirt ($100) in Apricot; Zara Pointed Slingbacks ($80) in White.

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    PHOTO: Stockholm Street Style

    Leather Pants + Bold Ankle Boots

    Think of your leather pants as a blank canvas and the perfect foundation for experimenting with a bold footwear choice. A graphic-print bootie not only gives the look an eclectic feel, it will help you break out of an all-black rut.

     

    Get The Look:
    Theyskens’ Theory Pittel Faux-Leather Leggings ($245) in Black; Loeffler Randall Felix Stacked Booties ($450) in Camel Dot Printed Calf.

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    PHOTO: Vanessa Jackman

    Tailored Shorts + Oxfords

    Play up the tomboy vibe of tailored shorts with a pair of menswear-inspired oxfords for a low-key, polished effect.

     

    Get The Look:
    Elizabeth and James Jody Floral Jacquard Shorts ($295) in Green; BDG Christina Wingtip Oxfords ($49) in Brown.

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    PHOTO: Stockholm Street Style

    Cropped Trousers + Strappy Mules

    Truthfully, cropped trousers lend themselves to a multitude of shoe pairings. If you’re looking for something a little edgy, go for a black leather slingback mule.  

     

    Get The Look:
    Sonia Rykiel Wool Pants ($740) in Ochre/Bordeaux; Alexander Wang Maryna Slingback Sandals ($575) in Black.

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    PHOTO: Stockholm Street Style

    Slouchy Pants + Bright Sneakers

    If you’re going for that luxe loungewear look, play up the sport angle with slouchy trousers and sneakers. A bright hue keeps the look feeling fashion-forward.

     

    Get The Look:
    Theory Arai Pants ($190) in Black; Saucony Women’s Jazz Original Sneakers ($53) in Pink/Bright Yellow

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    PHOTO: http://weworewhat.com

    Printed Trousers + PVC Pumps

    Your pants and shoes shouldn’t compete for the spotlight, so if you’re going for eye-catching on top, think minimal—a.k.a. see-through ankle-strap heels—on bottom.

     

    Get The Look:
    Girl by Band of Outsiders Silk Floral Pants ($385) in Navy; Gianvito Rossi Plexy Laser Pumps ($625) in Silver.

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    PHOTO: Stockholm Street Style

    Shin-Length Pencil Skirt + Low-Cut Pumps

    Play off the skirt’s long, lean silhouette with a pair of sleek pumps that have a low-cut vamp. Subtle toe cleavage plus a pointy shape gives the appearance of longer legs, which is always a bonus.

     

    Get The Look:
    Stella Jean Dofi-Print Pencil Skirt ($349) in Orange; Sergio Rossi Suede Pumps ($575) in Dusk.

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    PHOTO: Vanessa Jackman

    Leather Shorts + Strappy Sandals

    It’s easy for leather shorts to land in GNO territory, but simple, strappy sandals give them a daytime-friendly spin.

     

    Get The Look:
    Zadig & Voltaire Leather Simio Shorts ($485) in Black; Vince Camuto Vogue Metallic Snake-Print Sandals ($225) in Pale Gold.

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    PHOTO: Stockholm Street Style

    Cropped Jeans + Ladylike Pumps

    Cropped jeans that hit mid-shin are perfect for showcasing a pair of delicate pumps.

     

    Get The Look:
    J.Crew Cropped Vintage Straight Jeans ($168) in Cascade Wash; Steven by Steve Madden Ravesh Pumps ($149) in Olive.

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J.Crew Cropped Vintage Straight Jean

J.Crew Cropped Vintage Straight Jean

J.Crew, $168
SHOP
Ravesh Pump

Ravesh Pump

Steven by Steve Madden, $149
SHOP
Le Garcon Slouch Jean

Le Garcon Slouch Jean

Frame Denim, $199
SHOP
Two Tone Quarter Strap Sandal

Two Tone Quarter Strap Sandal

Chloe, $595
SHOP
Wool Pants

Wool Pants

Sonia Rykiel, $740
SHOP
Maryna Slingback Sandal

Maryna Slingback Sandal

Alexander Wang, $575
SHOP
Pittel Faux-Leather Leggings

Pittel Faux-Leather Leggings

Theyskens’ Theory, $245
SHOP
Felix Stacked Bootie

Felix Stacked Bootie

Loeffler Randall, $450
SHOP
Burnout Floral Midi

Burnout Floral Midi

Topshop, $100
SHOP
Pointed Sling-Back

Pointed Sling-Back

Zara, $80
SHOP
Leather Simio Short

Leather Simio Short

Zadig and Voltaire, $485
SHOP
Vogue Metallic Snake-Print Sandal

Vogue Metallic Snake-Print Sandal

Vince Camuto, $225
SHOP
Silk Floral Pant

Silk Floral Pant

Girl by Band of Outsiders, $385
SHOP
Plexy Laser Pump

Plexy Laser Pump

Gianvito Rossi, $625
SHOP
Jody Floral Jacquard Shorts

Jody Floral Jacquard Shorts

Elizabeth and James, $295
SHOP
Christina Wingtip Oxford

Christina Wingtip Oxford

BDG, $49
SHOP
Arai Pant

Arai Pant

Theory, $190
SHOP
Women’s Jazz Original Sneakers

Women’s Jazz Original Sneakers

Saucony, $53
SHOP
Suede Pumps

Suede Pumps

Sergio Rossi, $575
SHOP
Dofi-Print Pencil Skirt

Dofi-Print Pencil Skirt

Stella Jean, $349
SHOP
EXPLORE: Shopping, Shoes, Fall Trends, Shopping, J.Crew, Steven by Steve Madden, Frame Denim, Chloe, Sonia Rykiel, Alexander Wang, Theyskens' Theory, Loeffler Randall, Topshop, Zara, Zadig & Voltaire, Vince Camuto, Girl by Band of Outsiders, Elizabeth and James, Gianvito Rossi, BDG, Theory, Saucony, Sergio Rossi, Stella Jean, Theyskens’ Theory, Zadig and Voltaire, Steven by Steve Madden Ravesh Pump, Shopping, Trends
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