Fall Shoe How-To

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.

Colorblock wedges

$"Fall Shoe How-To" \\ Model wearing Colorblock Wedges$

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.

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1 of 10 Photo: Perry Hagopian

Chelsea boots

$"Fall Shoe How-To" \\ Woman wearing Chelsea Boots$

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.

2 of 10 Photo: Perry Hagopian

Bright t-straps

$"Fall Shoe How-To" \\ Model wearing red t-strap shoes$

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.

3 of 10 Photo: Perry Hagopian

Cap-toe flats

$"Fall Shoe How-To" \\ Woman wearing Cap-Toe Flats$

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.

4 of 10 Photo: Perry Hagopian

Over-the-knee boots

$"Fall Shoe How-To" \\ Model wearing Over-the-knee boots$

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.

5 of 10 Photo: Perry Hagopian

Menswear pumps

$"Fall Shoe How-To" \\ Model wearing menswear pumps$

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.

6 of 10 Photo: Perry Hagopian

Casual brogues

$"Fall Shoe How-To" \\ Model wearing Casual brogues$

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.

7 of 10 Photo: Perry Hagopian

Cut-out metallic heels

$"Fall Shoe How-To" \\ Model wearing Cut-out metallic heels$

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.

8 of 10 Photo: Perry Hagopian

Smoking slippers

$"Fall Shoe How-To" \\ Model wearing Smoking slippers$

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.

9 of 10 Photo: Perry Hagopian