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Finding the perfect pair of black boots is like finding the perfect pair of jeans: they’ve got to be comfortable yet versatile enough so you can wear them with pretty much everything. And when you find that perfect pair, well, there’s no taking them off.
To make your search easier, we asked top fashion editors to share their favorite boots of the season. So step up and take a look before they sell out!
And in case you missed it, check out the boot that two TODAY editors (and apparently the rest of the internet) are obsessed with here.
TODAY editors, writers and experts take care to recommend items we really like and hope you’ll enjoy! Just so you know, TODAY does have affiliate relationships. So, while every product is independently selected, if you buy something through our links, we may get a small share of the revenue.
1. Dr. Martens Flora Chelsea Boots, 75, Amazon
“Every fall, I find myself reaching for these boots because they're great in the rain/slush, and look cute with both jeans and dresses. I wore them nearly every single day of Fashion Week last February, and I expect to spend all winter in them this year, too,” notes Laurel Pantin, editorial and fashion director at Coveteur.
2. Nine West Front Pointy Toe Booties, $119, Zappos
“Revamping your fall wardrobe can get pricey, so I try to make sure my purchases are super-versatile and wearable, like these pointy toe booties. The shape of this shoe creates a very polished vibe, yet it can also look casual and cool when paired with denim. Plus, the heel height is high enough to look dressy, yet low enough that I can wear them all day without my feet hurting. In fact, I'm such a fan I bought them in two colors — wine and black!” says Sarah Ball, fashion market editor at People.
Get the look for less: Shoe brand Summerwhisper sells a similar stiletto bootie with a slightly lower heel for $38. They are currently marked down 60% from the original retail price!
3. Aerosoles Square Away, $130, Amazon
“Ankle length are always my go-to boots because I find them to be the most versatile to style; you can wear them with jeans, dresses, skirts, etc. I love this moto-inspired pair because of the edgy studded details and chunky stacked heel. They’re so comfortable I completely forget I’m wearing a 3-inch heel, even at eight months pregnant!” notes Sarah Gerrish, fashion market director at Redbook.
If you like the buckles, but you don't love the heel, Nordstrom's Topshop Krown Studded Bootie is for you.
4. Dolce Vita Cassius Ankle Booties, $140, Shopbop
“I love black boots in all shapes and sizes — they’re the most versatile shoe of the season. These booties are the perfect solution for when you want some height without the pain of 4 inches. The 2-inch block heel allows you to wear the boot from morning to night. Plus, I like how they already have that worn-in look, like you’ve owned them forever,” says Gabrielle Porcaro, senior fashion and market editor at Women’s Health.
Get the look for less: TODAY favorite brand, Sole Society has a suede ankle boot with a block heel that is nearly identical to Gabrielle's favorite! The ankle may not hit as high, but at 40% off you can't argue with the price!
5. Ariat Women’s Naturally Charcoal Santos Boots, $135, Amazon
“These cowboy boots are super comfortable, go great with dresses, jeans, basically everything. So comfortable, they were made to walk in — so they are perfect for living in New York City, where all I am doing half the time is running from one appointment to another,” says Jessica King, senior fashion and market editor at Martha Stewart Living and Martha Stewart Weddings.
6. Sam Edelman Kinzey Kitten Heel Bootie, $140, Nordstrom
“A short bootie with a tiny heel is the perfect boot to buy now and will actually stay on trend for seasons to come, as we saw this shape continue on the Paris runways at the spring/summer 2018 collections,” notes Kyle Anderson, fashion market and accessories director at Marie Claire.
7. Nine West Zadan Pointy Toe Booties, $99 (originally $119), Lord & Taylor
“Nothing screams fall like a black ankle boot, and this affordable pair has a Victorian-style polish that dresses up jeans or frilly dresses. I never thought I'd be into a kitten heel but this height is actually trending and perfect for running around the city,” says Jennifer Barthole, senior fashion editor at Shape.
8. Ash Hope Star Leather Booties, $215, Shopbop
“If you know me, you know I LOVE a Chelsea boot. It slips on easily and the heel is less than 2 inches, essential for a life that includes getting on and off the subway. The star embroidery on these boots gives them something a little special while remaining a basic, everyday boot,” notes Aya Kanai, chief fashion director, Hearst Women’s Fashion Group.
Get the look for less: Amazon's The Fix has a similar suede bootie with sequin stars and a higher heel, and a leather bootie with embossed stars both for $125. For only $35, Yoki sells an ankle boot with a rubber sole and star pattern.
9. Zara High Heel Sock-Style Ankle Boots, $59, Zara
“These sock boots are super comfortable and go with everything from jeans to dresses — and at $59 they won’t break the bank either,” says Jade Frampton, executive fashion market editor at Elle.
10. Sam Edelman Sondra Lace-Up Leather Ankle Boots, $225, Nordstrom
"This pair of boots delivers on both style and substance — and that's everything I'm looking for in a fall shoe. It's got to be cool, yes, but it also has to be functional with a walkable heel and a finish that's not too precious or pretty that I fear ruining them. This elevated riff on the hiking boot is the boot you'll live in — maybe not hiking — but everywhere else,” says Hannah Weil McKinley, content director at PopSugar Fashion.
11. Zara Leather Ankle Boot With Shimmery Heel, $119, Zara
"I love these black booties — they’re an update on the classic ankle style and the fun metallic heel gives them a glam feeling. I’ll wear them with long boho dresses and printed midi skirts from fall through winter. Bling on your boot? You can’t go wrong!" says Kristen Saladino, fashion director at Good Housekeeping.
12. Zara Over-the-Knee High Heel Boots, $70, Zara
“From December through late March, the streets in New York City are covered with snow and salt — translation: Shoes get ruined super easily. So I either wear wellies or boots I wouldn’t cry over if they were destroyed. This year, I love an over-the-knee boot because it keeps my legs warmer than tights,” notes Sarah Bray, style writer at Town and Country.
13. Schutz Mislane, $260, Schutz
“Form-fitting stretch boots are in this season and this suede version is my go-to shoe. They look great with cropped jeans, skirts and dresses! #winwin,” says Joiee Thorpe, fashion editor at Essence.
Get the look for less: For $159, Zappos sells a pair of Nine West boots that are incredibly similar. Steve Madden's Wagner boot sells at Nordstrom for $130 and comes in suede as well as patent leather.
14. Mango Over-the-Knee Heel Boots, $99, Mango
"I am OBSESSED with over-the-knee boots, but they must have a heel — a sensible heel! These instantly make me feel sexy in the dead of winter which is my secret weapon to combating winter blues,” says Tiffany Reid, fashion market editor at Cosmopolitan.
15. & Other Stories Pull-On Suede Boots, $195, Stories
“I love sock boots for their chic silhouette — cut close to the leg so they look feminine with skirts and tuck easily under skinny jeans. The heel on this one is walkable but gives you a little height, and suede is always a nice, rich texture for fall,” notes Stephanie Trong, fashion features director at InStyle.
Get the look for less: Jeffrey Campbell's Siren Bootie is available at Nordstrom for $125 and has a similar block heel and sock-like fit at the top.
16. Opening Ceremony Shayenne Suede Harness Ankle Booties, $450, Shopbop
“I live in motorcycle boots all season, and the sculpted 2-inch stacked heel on this style offers a little height and visual interest without sacrificing comfort. Plus the ankle harness strap adds a touch of Western trend without being too cheesy,” says Rachel LeWinter, senior market editor at Us Magazine.
17. Dolce Vita Dee Booties, $150, Zappos
“The kitten heel has made a huge comeback this year and I love it on boots or fall. This pair will make any outfit look extra chic,” notes Christina Holevas, style/accessories editor at Teen Vogue.
18. Aldo Kelii, $125, Aldo
“I am a big fan of a multipurpose boot that can be worn to work, dinner, parties and weekends. For me that means an ankle boot with a low, stacked heel. This year’s version is updated with a chic gold zipper to add a little more edge,” says Dori Katz Price, beauty and fashion director at Family Circle.
19. Cole Haan Jannie Waterproof Leather Chelsea Booties, $230, Bloomingdales
"As a busy working mom, I'm constantly on the go, from school to play dates to the office — so it's important to have stylish yet totally functional boots for the winter. That's why these gorgeous black booties, which have thick protective soles and are made of waterproof leather, are such game changers. They go great with jeans, or even a fabulous dress worn with a pair of colorful tights,” Jacqui Gifford, travel director at Travel + Leisure.