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Photo: Chris Craymer

Step lively in this season's gorgeous boots! We've rounded up the latest and greatest, including runway-inspired ankle stilettos, classic knee-high styles, edgy wedges, and yes, shbooties—along with tips on how to wear them all with flair.

A graphic black-and-white paddock boot gets even more playful when paired with socks. (If this look feels too young for you, opt for opaque black tights instead.) A patchwork play on menswear prints can also add zing to solid black outfits.

Left: Boots, Roger Vivier,  $2,395; 212-861-5371. Coat, Diane von Furstenberg, $598; Dress, Black Fleece by Brooks Brothers, $975; Bag, Kooba, $248; Tights, Bootights by Shelby Mason, $32;

Right: Boots, Fratelli Rossetti, $720; 212-888-5107. Coat, Ella Moss, $278; Shirt, Osklen, $347; 212-219-8250. Skirt, DKNY, $295; Socks, Falke, $24, The Sock Hop; 212-625-3105.
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Photo: Chris Craymer

Stack Attack
Boots with a stacked heel let you walk tall—but comfortably.

A fold-over, motorcycle-style boot looks great with a skirt and tights or skinny jeans.

Boots, Sigerson Morrison, $595; Coat, Marimekko, $399; Skirt, PinkTartan, $295; Bag, Pierre Hardy,$895; 646-449-0070. Tights, Falke, $69;
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Photo: Chris Craymer

Chelsea Lately
Orange accents update the classic '60s-mod Chelsea boot. It's the perfect weekend shoe, adding polish to jeans and skinny pants. (But don't wear these boots with leggings—your feet will look huge.) A flat sole means you'll be able to run a day's errands with ease.

Boots, DV by Dolce Vita, $129; Jacket, ClubMonaco, $329; for stores. Shirt, Oasis, $105; Pants, Zara, $30; for similar styles. Bag, LouisVuitton, $4,150; Socks, Falke,$44, The Sock Hop; 212-625-3105.

Photo: Chris Craymer

Walk This Way
A stiletto-heeled boot will always be a wardrobe essential. Wear ankle styles with dark tights so you don't visually shorten the leg. Pair a tall boot with a skirt that hits at or below the knee—but if you have to wear a shorter skirt, opaque tights are a must.

Left: Booties, Elie Tahari, $595; 212-334-4441. Sweater and skirt, Cynthia Rowley, $295 and $325; for stores. Watch, Gossip for QVC; $48; Gloves, Bruno Magli, $270;800-624-5430. Bag, IIIBeca by Joy Gryson, $158; Tights, Bootights by Shelby Mason,$32;

Right: Boots, L.K. Bennett, $695; 713-961-0009. Coat, Tory Burch, $850; Sweater, H&M, $50; Tights, Bootights by Shelby Mason, $32; Shot on location at Ladurée, NYC.
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Photo: Chris Craymer

Military green is an active-duty neutral: Pair it with darks and brights alike. The boot on the left blends fashion and function (the lug soles provide traction); the riding style on the right is extra comfy, with a foam footbed that contains Adidas shock-absorbing technology.

Left: Boots, Tory Burch, $450; Coat, L.A.M.B., $695; 877-850-9998. Sweater, L.L. Bean, $69; Pants, Paige Denim, $219; Bag, Marc by Marc Jacobs, $548; Socks, Falke, $44, The Sock Hop; 212-625-3105.

Right: Boots, Rockport, $220; Coat, Etienne Aigner, $895; Blazer, Marc Jacobs, $1,400; Sweater, The Limited, $50; Bag, Clare Vivier, $649; Tights, Falke, $38;
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Photo: Chris Craymer

Red Alert
The shbootie (a hybrid shoe–ankle bootie) is a cooler alternative to pumps. It looks fantastic with skirts, dresses, or pants, but be mindful of your hosiery situation. While black tights are fine with black shbooties, bare legs are best for colored versions.

Left: Boots, Aldo Rise x Preen, $230; Dress, Lela Rose, $1,195; Bag, Brahmin, $795; Watch, Isaac Mizrahi Live! for QVC, $40;

Right: Booties, Christian Louboutin, $1,095; Dress, Oscar de la Renta, $3,390; Bag, Mark Cross, $2,495; Watch, Timex, $55;

Photo: Chris Craymer

Berry Nice
Nothing says fall like richly colored suede, and here are two new ways to wear it: as a wedge (left), which offers stability and comfort without sacrificing chic; and as a bootie with a metallic cap toe (right)—the best accent for this season's metallic clothing and accessories.

Left: Booties, Cole Haan, $398; 800-201-8001. Coat, DKNY, $795; Pants, J.Crew, $248; Watch, Timex, $55; Bag, Mark Cross, $3,495;

Right: Booties, MIA, $89; Jacket, Tommy Hilfiger, $1,199; 212-223-1824. Skirt, J.Crew, $228; Socks, Hue, $14; Bag, Lauren Ralph Lauren, $268; Shot at the Smith, NYC.

Photo: Chris Craymer

Booting Up
Rich brown-leather details elevate black boots (left); cream is an unexpected and fashion-forward choice for the ones on the right. How to wear a pale shoe with confidence? Don't pair it with matching tights—it's too nursey. Go with a bare leg or, if you must cover up, choose cream fishnet stockings.

How to Care for Your Boots

Tips from Joseph Rocco Jr. of Jim's Shoe Repair, NYC:

Spray leather and suede with water-and-stain protector before you wear them for the first time. (Patent can go without.)

Once your leather boots are weatherproofed, shine them up with a shoe cream (Rocco recommends Meltonian) instead of a wax, which may not allow leather to breathe and can cause it to crack.

Have a shoe repair shop add a thin rubber sole to your boots, for traction and an extra layer of protection. (Wear the boots a few times beforehand; a rougher sole helps the new layer adhere better.)

Left: Boots, Bally, $950; 212-751-9082. Dress, DKNY, $595; Bag, Zac  Zac Posen, $495;

Right: Boots, Gianvito Rossi, $1,020; Dress, CH Carolina Herrera, $1,045; 212-744-2076. Watch, Anne Klein $65; Bag, Marc by Marc Jacobs, $548; 212-924-0026. On twins: Jackets, $25 each, onesies, $13 for three, pants, $15 each, and shoes, $13 each, The Children’s Place;

Next: How to wear jeans at the office