The Fall 2018 Boot Guide

Forget sweater weather—fall is the time for gorgeous, versatile, wonderful boots. Whether slouchy or structured, to the knee or skimming right above the ankle bone, there’s a boot for everyone.

Expanded sizing makes that last point especially true: Stuart Weitzman recently announced that most styles are now available in sizes 4 through 12 and three different widths. A boon always, it’s especially good news for boot season when higher rises and calf-hugging styles can make the just-right fit tricky.

Below, key styles to pay attention to and how to wear them.

The Combat Boot

Toughen up feminine silhouettes and fabrics with this classic kicker.

Tough, no-frills-attached combat boots feel just right for grounding any outfit this fall. The key elements to the classic style are still there—think lace hooks, rounded toes, and sturdy soles—but they’ve been made to feel style-forward with new elements. Beautifully non-work-boot shades like gray violet liven up a look; quilted leather and chunky heels provide a feminine feel.

This season, give combat boots life beyond the jeans-and-sweater section of your wardrobe. Toughen up luxe fabrics like silk and leather, and perfect a stylish juxtaposition by pulling them on with skirts and dresses. Standard boot IQ would have you think a nubby sock is best to wear underneath, but, surprise!, styling with sleek hosiery works just as well.

Shop the trend:

Worn with: (top) Self Portrait Coat, $570; Redemption Tank, $288; 3×1 Leather Pants, $995; Wolford Socks, $29; Jennifer Fisher Ring, shop similar (bottom) Beaufille White Blouse and Skirt, information upon request; Lady Grey Earrings, $132; Billy Reid Turtleneck, $495; Alberta Ferretti Skirt, $1,095; Jennifer Fisher Rings and Necklace; Wolford Tights, $49

The Over-the-Knee Boot

Think of OTK styles like a leather legging layer.

Thigh-grazing boots are sexy by nature, but in a Venn diagram they’d also be encircled by the “practical” and “perfect for chilly weather” circles. Wearing them with skinny jeans is quick, easy, and sleek, but layering them with gauzy dresses and minis will convince you that you can’t live without them.

Take a look in your closet and pick out the pieces that are typically relegated to the back once summer wraps up. Now, bring them front and center. They’re utterly wearable when you think of a chic OTK boot as a leather legging, adding another layer to keep you warm. Reconsider what you’re tucking in too. The really daring can try folding jumpsuits and silky joggers into a pair.

Shop the trend:

Worn with: (top) A.P.C. Joan Coat, $645; Kamperett Duster Coat, $485, and Bodysuit, $275; Wolford Tights, $35; Seline Kent Jewelry (bottom) Isabel Marant Dress, $1,025; Jennifer Fisher Bracelets and Ring; Cienne Blazer, $890, and Pants, $720; Jennifer Fisher Ring

The Sock Bootie

Take mid-calf hemlines into fall with ankle-hugging boots.

Emerging onto the shoe scene last fall, the sock bootie is still here and ready to become part of your seasonal uniform. Defined by an ankle or mid-calf silhouette that hugs the leg, it’s perfect for wearing with cropped jeans or midi dresses.

Their shape echoes the primness of Victorian style lace-ups when worn with feminine dresses; paired with cropped jeans or trousers, they’re a tool for handling chillier fall weather. While typical booties can be tricky with a hemline that hits right at the top of the shoe, the tight fit of a sock style means it easily slips under the leg of your pant for a streamlined look.

When styling with dresses, use a pair to replace classic pumps. For a statement look, invest in a bold shade and build a monochromatic outfit.

Shop the trend:

Worn with: (top) Prabal Gurung Dress, $1,495; Jennifer Fisher Earrings; 3×1 Shirt, $265, and Jeans, $225; (bottom) Beaufille Dress, $620; Lady Grey Earrings; Jennifer Fisher Rings; Wolford Socks, $29

The Flat Ankle Boot

This easy-to-wear style goes with, truly, everything.

Simple in attitude, sure, but don’t underestimate the flat ankle boot. This fall we’re urging you to push the outfit boundaries by styling a pair with cocktail dresses or other pieces that typically call for a heel. It adds a stylish flair and displays a whole lot of personality (plus, it’s unquestionably more comfortable).

The practicality aspects you’ve always loved about the flat boot are what makes it such a nice contrast for high-octane fashion pieces too. Try it as a finishing touch with sculptural jackets or oversized shapes.

Shop the trend:

Worn with: (top) Prabal Gurung Blouse, $1,495, and Skirt, $1,145; Jennifer Fisher Rings; Isabel Marant Dress, $1,825; Jennifer Fisher Earrings (bottom) Camilla and Marc Coat, $714

The Statement Boot

Take any outfit up a notch with color or sculptural details.

Boots find themselves in the “sensible footwear” category most often, but what if standout fabrics, museum-worthy sculptures, and serious sparkle were added to the equation? Cast a bold pair as your statement accessory this fall, keeping the rest of your outfit subdued to let them have a full moment.

A galaxy of multi-colored crystals is our favorite complement to an LBD, while an ’80s-inspired pair becomes the exclamation point in a monochromatic combo. If you prefer to fly a little closer to the radar, look for a classic shape with a twist. A sculptural heel in metallic gold is just the ticket.

Shop the trend:

Worn with: (top) Galvan Dress, $1,175; Lady Grey Lucite Earrings, $180; Camilla and Marc Dress, $499; Jennifer Fisher Rings (bottom) Calvin Luo Jacket, $270, and Skirt, $250; Jennifer Fisher Jewelry

Photographer: Harper Smith, Stylist: Lindsay Grosswendt, Hair: Leonardo Manetti, Makeup: Rommy Najor