Fall Shoe How-To

Fall Shoe How-To
Photo: Perry Hagopian

Fall Shoe How-To

01 of 10

Fall Shoe How-To

Fall Shoe How-To
Perry Hagopian

A new season, a big new challenge: what really goes with fall's freshest flats, boots and stilettos? We walk you through the season's hottest styles and how to make them work.

02 of 10

Colorblock Wedges

Fall Shoe How-To
Perry Hagopian

A great mate for minis, matchstick pants, and slim jeans, these are chicest when worn with something that picks up at least one of the shoe's colors.

Shop the Look: Silk shirt, Lacoste, $215; lacoste.com. Wool pants, Paul Smith Black Label, $520; 646-613-3060. Suede wedges, Pierre Hardy, $500; 646-449-0070.

03 of 10

Chelsea Boots

Fall Shoe How-To
Perry Hagopian

These are as at home with a lamé dress on a big night out as with short skirts or sleek trousers for day. Be sure your pants cover the tops of the boots to avoid a chopped-at-the-ankles look.

Shop the Look: Denim and leather jacket, Maison Scotch, $265; saksfifthavenue.com. Wool-polyester dress, Whit, $399; eatontradingcompany.com. Leather boots, Red Valentino, $525; at Valentino.

04 of 10

Bright T-Straps

Fall Shoe How-To
Perry Hagopian

Red plus stiletto equals major sex appeal, so pair these with something demure like a ladylike skirt (long or short) or with jeans to dress them up for a Saturday date. To really elongate legs, the ankle strap should hit below your ankle bone.

Shop the Look: Acrylic-angora sweater, Porter Grey, $325; shopbop.com. Silk blouse, Kahlo, $264; satineboutique.com. Rayon-nylon skirt, BCBG Max Azria, $138; at Bloomingdale's. Resin, lizard skin, and gold plated bangles, Kara by Kara Ross, $145 each; kararossny.com. Studded leather T-straps, Schutz, $180; piperlime.com.

05 of 10

Cap-Toe Flats

Fall Shoe How-To
Perry Hagopian

Comfortable enough to commute in and cute enough to wear all day at the office, these flats are adorable with jeans, slim pants, or a knee-length pencil skirt that's tapered at the hem so it doesn't seem dowdy.

Shop the Look: Cashmere cardigan, Boden, $138; bodenusa.com. Cotton-polyester T-shirt, Nation LTD, $74; nationltd.com. Polyester-wool skirt, By Malene Birger, $395; hampdenclothing.com. Cubic zirconia and gold plated necklace, Betty Carré, $65; bettycarre.com. Brass watch with leather strap, Timex, $45; timex.com.

06 of 10

Over-the-Knee Boots

Fall Shoe How-To
Perry Hagopian

Combined with the skinniest jeans, these will make your legs look Gisele Bündchen-long. They also go with skirts, but avoid the Pretty Woman effect by ensuring the hem covers the tops of the boots.

Shop the Look: Wool-elastane jacket, Tocca, $495; 212-255-3801. Cotton shirt, Chance, $68; chanceco.com. Denim jeans, 3X1, $245; barneys.com. Gold tone bracelet, Michael Kors, $145; michaelkors.com. Gold tone watch, Michael Kors, $250; at select Michael Kors stores. Suede boots, Report Signature, $315; shoes.com.

07 of 10

Menswear Pumps

Fall Shoe How-To
Perry Hagopian

These dolled-up penny loafers are stylish with tailored trousers or when playing against type with sporty separates or a girlie dress.

Shop the Look: Fleece and leather pullover, Love Zooey, $189; lovezooey.com. Cotton-wool-viscose shorts, Burning Torch, $225; 310-399-1920. Rope, metal, and enamel paint bracelet, Orly Genger by Jaclyn Mayer, $125; jaclynmayer.com. Rhinestone and antiqued silver plated cuff, Giles & Brother, $225; gilesandbrother.com. Leather pumps, Tommy Hilfiger, $89; piperlime.com.

08 of 10

Casual Brogues

Fall Shoe How-To
Perry Hagopian

Add a Y chromosome touch to flouncy skirts and slim pants in feminine colors and patterns. They gray hue is ideal for transitioning from summer to fall.

Shop the Look: Wool-viscose coat, Theonne, $518; theonne.com. Denim shirt, Graham & Spencer, $174; grahamandspencer.com. Cotton pants, Maje, $320; us.maje.com. Suede and metal cuff, Max Mara, $390; 212-879-6100. Faux leather bag, Aldo, $55; aldoshoes.com. Suede brogues, Jean-Michel Cazabat, $295; 646-669-8508.

09 of 10

Cut-Out Metallic Heels

Fall Shoe How-To
Perry Hagopian

While these are stunning with cocktail dresses, they work for day too. In fact, gold is a neutral that goes with all your nothing-matches-this outfits.

Shop the Look: Viscose-wool and alpaca wool top, Generation Love, $178; shopbop.com. Lambskin skirt, Vince, $1,050; at Vince. 14kt gold and oxidized silver, or sterling silver cuff, Loren Stewart, $175-$350; lorenstewart.com. Metallic leather heels, Rupert Sanderson, $920; rupertsanderson.com.

10 of 10

Smoking Slippers

Fall Shoe How-To
Perry Hagopian

A fresh alternative to ballet flats, these are equally versatile, playing well with minis and cropped pants. Don't be afraid to wear them with prints-as long as the shoes and clothes have at least one color in common. What not to pair them with? Wide-legged pants, long skirts, and tights.

Shop the Look: Mohair with faux-pearl detail cardigan, Girl by Band of Outsiders, $349; net-a-porter.com. Silk dress, Joie, $198; 202-338-9465. Gold fill and gold vermeil necklace, Sonyarenee Jewlery, $48; sonyarenee.com. Brass bracelet, ALC, $465; at Saks Fifth Avenue. Printed satin slippers, Charles Phillip Shanghai, $135; shopbop.com.

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