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This year has us turning up the volume on our day-to-day wardrobe with ankle boots that are meant to stand out rather than blend into the background. Here are the six biggest bootie trends to stock up on, plus tips on exactly how to wear them for a super-stylish start to 2020.

RELATED: 6 Trends New York City Women Can’t Stop Wearing


The beloved ’90s grunge footwear is back with a vengeance, and flat Dr. Martens are popping up everywhere. Classic black leather is still the most popular option, but deep burgundy, white and even high-shine patent styles are tied for a close second, if you’re hoping to shake things up.

woman wearing combatboots and a silk skirt
Edward Berthelot/Getty Images

Wear Them With: Opposing Fabrics

Our favorite way to rock combat boots is with pieces that totally oppose their tough vibe. Silk slip skirts, cream-colored cashmere sweaters and ladylike handbags all give your Dr. Martens a much more sophisticated and modern upgrade. Just make sure your skirt goes no longer than mid-calf so your legs aren’t overwhelmed by so much fabric.

Shop similar styles: Dr. Martens boots ($150); Free People jacket ($198); Inhabit sweater ($348; $208); Silk Laundry skirt ($230); Saint Laurent bag ($2,290)

woman wearing combat boots and jeans
Edward Berthelot/Getty Images

Wear Them With: Straight-Leg Jeans and a Structured Top

Try something unexpected on top, like a tailored blazer or preppy cotton shell. This is an instance where we’d suggest skipping wide legs or a boyfriend cut, as the excess fabric will look sloppy paired with clunky footwear.

Shop similar styles: ASOS boots ($62); Mango blazer ($100; $80); CeCe top ($89; $45); Good American jeans ($159)



Bring on kicks in hot pink, bold red, electric blue and vivid green for a fabulous pop of color. While you could try a colorful lace-up or embellished bootie, we think this trend looks best with a simple, sleek silhouette and a pointed or square toe shape. That way, the brilliant hues can really shine.

woman wearing bright blue boots
Kristin Sinclair/Getty Images

Wear Them With: Black-and-White Prints

An attention-grabbing pop of aquamarine is all you need to inject some pizzazz back into the black-and-white sweater you’ve had for years and bring new life to a classic houndstooth coat. Of course, throwing on a few additional colorful accessories can’t hurt either, whether they match your boots or not. The trick to rocking multiple brights at once? Only add complementary colors to the mix (e.g., wearing green or purple with blue, or orange or pink with red).

Shop similar styles: P.A.R.O.S.H. boots ($305; 215); Alice + Olivia coat ($660; $165); Maison Fabre gloves ($215)

woman wearing red boots with a apurple dress
Daniel Zuchnik/Getty Images

Wear Them With: Neighboring Shades

Lean hard into a colorful outfit by pairing your ankle boots with prints and patterns in similar hues (e.g., red with pink, purple and orange). The end effect is just as flattering as a monochrome look, but a bit less bold, which makes getting dressed a morning affair.

Shop similar styles: MICHAEL Michael Kors boots ($160); Ulla Johnson top ($325) and skirt ($495)



Yes, the exotic animal print is still going strong into 2020. It doesn’t matter whether you prefer a more realistic gray or brown coloration, or if you go totally faux with red, purple or rainbow, so long as you wear ’em proud. Treat snakeskin as a neutral; the print can be rocked with almost any color, fabric or pattern in your wardrobe.

woman wearing snakeskin boots and purple outfit
Hanna Lassen/Getty Images

Wear Them With: Monochrome Ensembles

Solid-colored boots, while not a terrible choice, don’t add much to a tonal look. Throw a print into the mix, however, and you suddenly find your outfit has much more depth and interest thanks to some strategically placed scales. Gray snakeskin works best for cool colors like purple, navy blue or forest green, while brown or even yellow-tinged scales look better with warmer shades like burgundy or caramel. 

Shop similar styles: Marc Fisher Ltd boots ($220); Court & Rowe sweater ($99; $50); & Other Stories skirt ($79)

woman wearing snakeskin boots and jeans
Matthew Sperzel/Getty Images

Wear Them With: All Your Basics

Whenever you would normally reach for classic black boots, pull on your snakeskin pair instead. This year we plan to treat the animal print as a true basic, which means we’ll be wearing our snakeskin boots with a striped turtleneck and a floral cardigan, in addition to a fancy silk slip dress. Anything goes, but avoid wearing this pattern with zebra or leopard print. This isn’t the zoo! 

Shop similar styles: Steve Madden boots ($110); Sam Edelman coat ($99; $75); Heartloom sweater ($130); Rebecca Taylor La Vie jeans ($195)



For better or worse, the sky-high style is back. This time around they feature large block heels and smooth, unadorned leather, primarily in neutral hues like black, brown and cream. Basic is better, at least when it comes to the tallest shoes of 2020.

Wear Them With: A Straight Pencil Skirt

A hip-hugging skirt helps balance the proportions of an oversize shoe, but don’t go too tight. Think along the lines of a straight, structured silhouette rather than an Herve Leger bandage skirt.

Shop similar styles: MICHAEL Michael Kors boots ($199; $80); Petite Studio jacket ($289) and skirt ($149)

woman wearing platform boots and jeans
Edward Berthelot/Getty Images

Wear Them With: Raw Denim and Menswear

Black platforms look best with pieces that stand in stark contrast to the style’s goth, punk and disco history. Think ’60s blue boilersuits, Cher Horowitz–inspired skirt suits and tailored menswear.

Shop similar styles: Missguided boots ($64); Club Monaco coat ($479; $240); Lee jumpsuit ($138)



Slimmer and more ladylike than other lace-ups (combat and hiking boots, we’re looking at you), the Victorian style adds a posh finish to jeans and skirts alike. Aim for pairs with either a classic block heel or slick stiletto, rather than an ornate cone or a curved detail. Steer clear of over-the-top embellishments or you may end up looking like you’re wearing a costume.

woman wearing black victorian boots
Melodie Jeng/Getty Images

Wear Them With: An Oversize Cardigan and Jeans

Balance the prim nature of Victorian boots with an otherwise super casual outfit. Loose jeans with a hem that hits just below the top of the boot and a chunky sweater should do just the trick. You’ll feel comfortable, but you won’t look messy at all.

Shop similar styles: Schutz boots ($295); Naadam cardigan ($250); J.Crew turtleneck ($37); Agolde jeans ($168)

woman wearing beige victorian boots
Matthew Sperzel/Getty Images

Wear Them With: An A-Line Skirt

If you want to sport your Victorian booties to work, brunch or even dinner, we suggest playing up the ladylike feel. A structured two-piece suit will feel too stiff or buttoned up, but an A-line skirt that hits mid-calf is just flowy enough. Plus, it shows off all the gorgeous detail of your kicks. Top it off with a slim-fit sweater, simple blazer or cozy cardigan.

Shop similar styles: Alexandre Birman boots ($692; $415); Treasure & Bond blazer ($99); Commando bodysuit ($88); 3.1 Phillip Lim skirt ($450)



Another style that’s carrying over from 2019 is the square toe. These angular boots can come in a wide range of silhouettes: western, Victorian, block heel, you name it. But don’t be intimidated by the shape—it’s actually really easy to wear.

Wear Them With: A Leg-Baring Dress

Square toes innately feel pretty retro thanks to their popularity in the ’90s, but wearing them with a modern dress, like a romantic prairie style, instantly bumps the boots to a newer, cooler level. That said, it’s very important to pay attention to hem lengths. Avoid anything that lands more than an inch below the top of the boot (really, knee-length is probably your best bet) or you might take on a sort of colonial woman feel—and that isn’t exactly trending right now. 

Shop similar styles: Lulus boots ($69); Ganni dress ($586)

woman wearing blue square toe boots
Kristin Sinclair/Getty Images

Wear Them With: Wide-Leg Pants

Dresses not really your style? Try a pair of wide-leg pants in whatever fabric you’d like (denim for the weekend, wool crepe for work) that hit right at the midpoint of your foot. While pointy-toe boots look fabulous with pants in a matching hue (and give you supermodel legs in the process), square toes look best in contrasting shades, so have some fun with light-blue kicks and brown trousers or camel-colored footwear and winter-white bottoms.

Shop similar styles: Schutz boots ($290); Proenza Schouler coat ($975); Tory Burch blouse ($398); Universal Standard pants ($130)

RELATED: Katie Holmes Just Brought Back Her Tiger Print Boots (and Paired Them with Black Culottes)

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