Updating your wardrobe for fall is about more than swapping out your t-shirts for cardigans and topping your coat off with cozy scarves: It also requires a change of footwear. Breezy, open sandals are prone to give way to warmer, more covered styles, with the best boots for fall reigning supreme as the top picks of the season.
There are several factors to consider when sussing out the right pair to invest in. Read on for some of the most important things to keep in mind while shopping for boots below.
Boot Style: Boots come in all different styles, from booties and ankle boots to over-the-knee (think riding or thigh-high boots). Some will favor those with chunkier heels, like block heels or wedges, which make them easier to walk in, while others prefer the beloved stilettos seen in high-heel options.
Boot Heel Height: Speaking of heels, the “right” boot heel height will vary greatly from person to person. If you’re someone for whom comfort is of high importance or you suffer from foot issues, such as bunions or plantar fasciitis (a condition in which the bottom part of the foot is inflamed), you’ll likely want to go with a flat boot or one with a low heel (department stories typically characterize a low heel from 1 to 2 inches). If you’re more concerned with aesthetics, however, you may prefer a high heel, typically ranked between 3.5 to 4.5 inches and above. A standard heel falls between 2 to 2.5 inches.
Boot Material: The material your boot is made from can make a world of difference from how long your shoe lasts to how it makes you feel. Suede, for instance, while handsome, makes for a less-than-stellar choice for those who live in snowy areas where staining salts are regularly tossed onto the sidewalks. Smooth, long-lasting leather may be the preference of many, but animal advocates may prefer a synthetic material, such as polyurethane.
Boot Sizing: Fitting your leg for a boot goes beyond your run-of-the-mill numbered sizing: You’ll also want to make sure you’ve properly measured your calf before ordering. To do so, wrap a cloth tape measure around the fullest part of your lower leg. A narrow calf is typically one that measures less than 13.75 inches around, while a wide calf typically fits those with a circumference of 16 inches or more.
The Best Fall Boots of 2019
We’ve researched hundreds of boots to come with a list that caters to every style, height, material, and size preference. Keep scrolling for Woman’s World’s top picks for the best fall boots of 2019.
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Sam Edelman Penny Riding Boots
Best Riding Boots — Sam Edelman Penny Leather Boot
Where to buy: $149.90, Nordstrom
Riding boots may have been created centuries ago and used for everything from military uniforms to equestrian gear, but today, they’re one of the most popular boot styles around. Sam Edelman’s gives a modern take on the old classic in this Penny version, which features all of the markings of a true riding boot that's typically characterized by a knee-length height, a sturdy toe, and a low, distinguished heel. They’ve also got an elastic gore for give at the shaft, a 1-inch heel, and a back zipper.
Zi Gi Saray Boots
Best Slouchy Boots — ZiGi Saray Boots
Where to buy: $59.99 (Originally $79), Belk
These affordable slouched boots are just the right height for scrunching up over a pair of jeans. They’ve got a 3.25-inch heel for those that like a more elevated shoe, and a slip-on style for easy on and off.
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Lauren Ralph Lauren Eastwell Dress Boots
Best High Heel Boot — Lauren Ralph Lauren Eastwell Leather Dress Boots
Where to buy: $185, Macy’s
If you’re looking for something slightly more elevated, check out these leather finds from Lauren Ralph Lauren. With a 2.75-inch heel, they’re still low enough to keep from killing your feet, but high enough to command instant attention. They're also slightly thicker than most skinny heels, leading us to believe they'll stand up slightly better than most. A side buckle adds a nice, polished touch.
Wonders Block Heel Bootie
Best Block Heel Boot – Wonders Leather Block Heel Bootie
Where to buy: $274.95, Nordstrom
Block-heel boots are a favorite because of their wide, walkable bottoms and high functionality. This Spanish-made Wonders design draws the eye in with intriguing asymmetrical zipper detailing and a smooth, sleek leather finish. These boots also feel like a dream thanks to their memory gel footbed.
Chinese Laundry Kristin Cavallari Lash Bootie
Best Peep Toe Booties — Chinese Laundry Kristin Cavallari Lash Suede Ankle Bootie
Where to buy: From $119.46, Amazon
Part summer shoe, part fall, these gorgeous peep-toes are the perfect pick for making the seasonal transition. They're available in three warm autumnal hues and encase your ankle in cozy, 100 percent kid suede while allowing your tootsies plenty of room to breathe.
Charles By Charles David Viceroy Boots
Best Over the Knee Boots – CHARLES by Charles David Viceroy Boots
Where to buy: $159, Nordstrom
Over-the-knee boots have been fashion staples since the 1960s, when Balenciaga first sent them down the runway. They’re still every bit as stylish today, with women of all ages pairing them with dresses, skirts, over jeans, you name it! We’re particularly fond of these synthetic Charles David numbers, which feature a 3.35-inch block heel, an open back slit at the top of the shaft, and a side zipper.
Best Moto Boots — UGG Wilde Leather Moto Boots
Where to buy: $195, UGG
You’re no doubt familiar with the tall suede brown UGGs that hit the streets in full force come this time of year, but the company also makes some seriously quality motos. Not only are these Wilde boots more edgy than UGG's regular kicks, they’re designed a bit differently, too, with a waterproof exterior, a cushioned insole, and a molded rubber outsole. Inside, however, you'll find the same cushy UGGPure lining you’ve come to know and love, which means your feet will stay just as cozy as they do dry.
Solemani Paradise Boots
Best Boots for Narrow Calves — SoleMani Leather Paradise Boots
Where to buy: $189.99, Amazon
If you tend to look like you’re drowning in tall boots with too-wide shafts, you’ve met your match in SoleMani’s leather Paradise boots, which are specially made for those with slim calves, beginning at 12 inches.
Amazon customers agreed they make for the perfect fit, with one writing, “They fit tight around my skinny legs and they are so comfortable that I can walk around in NYC all day in them.”
Added another: “I am so thrilled to finally find a brand that makes boots that FIT on my legs and hug them nicely, rather than gapping and being so loose around my leg.”
Best Boots for Wide Calves — Torrid Braided Knee-High Boots
Where to buy: $74.90, Torrid
If you’re on the opposite end of the spectrum and struggle to find shafts that are wide enough to fit your calves, Torrid has you covered with its faux suede braided knee-high boots. They’ve got a “true” wide width that will fit snugly without being too tight and back goring, or a bit of stretch elastic, for even more give.
Madewell Reagan Boots
Best Pull On Boots — Madewell Reagan Leather Boots
Where to buy: From $178, Nordstrom
If you’re not keen on all the lacing, stuffing, and strapping that comes along with most seasonal footwear, may we present this pull-on style from Madewell? Designed with elastic sides to offer your ankle more give, they can be slipped on and off with ease. They come in a mix of prints and materials (choose from leather or calf hair), and their extra-padded footbed offers up a bit of added support.
Hunter Original Tour Adjustable Rain Boots
Best Rain Boots — Hunter Original Tall Back Adjustable Boots
Where to buy: $160, Hunter
When it comes to rain boots, no brand holds a candle to Hunter. We like this pair for the adjustable back that allows you to tighten or loosen the gusset as needed. With a natural rubber exterior, they’re completely waterproof, with a polyester lining. A pro tip: While your feet will stay dry in any of the brand’s vulcanized (hardened rubber) footwear, you may also want to nab a pair of Hunter’s boot socks ($30) as a buffer between your feet and the chilly rubber.
Cole Haan Eneida Wedge Boots
Best Wedge Boots — Cole Haan Leather Eneida Wedge Boots
Where to buy: $129.46 (Originally $220), Cole Haan
Leave it to Cole Haan to take a stylish design, like the ever-popular wedge boot, and make it fully optimized for comfort. The fashion house has added its cushioned grandføam technology to the footbed of these kicks to make them extra snug. That makes their low, 2-inch heel — complete with rubber traction — ideal for those need to stand or walk in them for prolonged periods.