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.

  • Shoes
    Photo credit: 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.

     

  • Shoes
    Photo credit: 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.

  • Shoes
    Photo credit: 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.

  • Shoes
    Photo credit: 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.

  • Shoes
    Photo credit: 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.

  • Shoes
    Photo credit: 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

  • Shoes
    Photo credit: 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.

  • Shoes
    Photo credit: 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.

  • Shoes
    Photo credit: 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.

  • Shoes
    Photo credit: 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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