When it comes to our winter wardrobes, it can be easy to get stuck in a leggings rut. While these comfy-chic pants will always have a place in our hearts (and our closets), your wardrobe deserves some elevation — even while it’s cold outside. Enter leather pants. Not only are they trending at the moment, but leather pants are an easy way to make even the simplest of outfits look a little more curated. Ad unlike the ultra-skinny fits of yesteryear, there’s a plethora of relaxed and breathable fits that take an “out of the box” perspective on the classic pant, making them more wearable than ever.
“A good leather pant is a winter essential these days for both warmth and style,” says Elizabeth Kosich, NYC-based professional stylist. “Be it a legging, trouser or bootleg cut, the leather pant is a classic that can be dressed up or dressed down.” That’s the best part about leather pants — they’re surprisingly versatile. From meeting to date night, this chameleon of a pant fits into your daily wardrobe far more seamlessly than you might imagine. Need some style inspiration? We’ve got you covered. Below, check out our expert-approved leather pants outfits to try this season.
Power up
Heading to the office? David Zyla, Emmy Award-winning stylist and author, recommends giving your leather pants the 9-to-5 treatment with your favorite button-up. “Play up your power by pairing leather pants with a crisp button-front shirt,” he says. “For a less formal version, knot the shirt tails at the waist and add a knit vest.”
Wear The Look:
L’Academie The Bisous Leather Pant ($279; revolve.com)
A cinched waist and relaxed leg create a modern silhouette.
Madewell Flannel Classic Ex-Boyfriend Button-Back Shirt ($75; madewell.com)
This play on the classic button-down is actually a popover top, with a — surprise! — full row of buttons down the back.
Charter Club Ribbed Cashmere Duster Vest ($90; macys.com)
A simple duster vest can add long lines and a chic touch to any outfit.
Business Casual
Looking for another way to spice up your office attire? Go for an on-trend wide-leg leather pant. “Add a blazer, over-sized white shirt, and kitten heels to look professional, then accessorize with a classic watch, pearl necklace or smart handbag to ground the look and add some polish,” says Kosich.
Wear the look:
Ann Taylor Petite Faux Leather Wide Leg Crop Pants ($98; anntaylor.com)
Not into ultra-tight skinny silhouettes? Then the wide-leg option is the perfect fit for you.
Majorelle Rhea Blazer ($168; revolve.com)
A plaid blazer is essential for any winter wardrobe (and beyond).
Schutz Danica Kitten-Heeled Mules ($160; anthropologie.com)
Snakeskin is trending, and you can never go wrong with a classic mule.
Simply Chic
Want to keep it low-key? “Let the leather pants be the focal point of your outfit and pair them with a relaxed t-shirt or henley top and vintage sunglasses,” Zyla recommends.
Wear the look:
A New Day Women’s Slim Fit Mid-Rise Faux Leather Leggings ($25; target.com)
The classic fit, under $30—what else could you ask for?
Urban Outfitters Out From Under Scarlett Notch Henley Top ($24; urbanoutfitters.com)
Meet your new favorite long-sleeve V-neck.
Michael Kors CHELSEA Sunglasses ($99; macys.com)
Classic aviators top off the look.
Winter Uniform
Kosich’s go-to leather pants outfit for the winter? Pairing a cropped pant with vintage fur and sneakers, which she’s dubbed the “ultimate cool-girl look” for winter. “Often seen on the streets of New York and London, this look delivers on comfort, style, and warmth, making it my favorite winter uniform of all time,” she says.
Wear the look:
Sandro Leather Ankle Pants ($745; bloomingdales.com)
Look for a pair that hits a few inches above your ankles.
Compania Fantastica Wild Thing Faux-Fur Coat ($189; modcloth.com)
Vibrant blues and cheetah prints: a match made in punk heaven.
Converse Women’s Chuck Taylor High Top Sneakers ($55; macys.com)
A classic “cool-girl” sneaker that will tie any outfit together, no matter the season.
Date Night
Whether it’s a first date or your 10th, tuck away your LBD and try shaking things up with some leather. “Leather is a great way to amp up your sex appeal for date night,” says Kosich. “Pair your leather pants with a cold-shoulder top or silky camisole to strike a balance of sweet-and-sexy.”
Wear the look:
Nordstrom Faux Leather Leggings ($69; nordstrom.com)
An ultra-skinny leather legging is perfect for showing off your stems on date night.
Lovers+Friends Anisa Turtleneck Sweater ($98; revolve.com)
Upgrade your turtleneck sweater with a cold shoulder cut.
J. Crew V-Neck Camisole ($50; jcrew.com)
A satin cami is a simple and sexy way to elevate your outfit.
Western Wear
The Western trend was full-force last year, and it doesn’t seem to be going anywhere in 2020. “Take a cue from western wear and pair leather pants with denim in the form of a button-front shirt or updated jean jacket or duster,” says Zyla.
Wear the look:
Free People Penny Flared Faux Leather Pants ($47; bloomingdales.com)
A bootleg cut like these offers a subtle play on western Americana.
Petersyn Almira Blouse ($68; shopbop.com)
Give your Western-inspired ‘fit a feminine touch with ruffle details.
Levi’s Dad Sherpa Trucker Jacket ($128; urbanoutfitters.com)
Or, go for a denim jacket with a warm sherpa lining.
Weekend Warrior
“Nothing says after-hours like leather,” says Kosich. “So pair your leather pants with Dr. Martens and a winter coat, and rock the look straight through to Monday.”
Wear the look:
Abercrombie & Fitch Ultra High Rise Faux-Leather Paperbag Pants ($78; abercrombie.com)
A relaxed-fit leather pant, for your relaxed weekend.
Dr. Martens 1490 10-Eye Boot ($150; urbanoutfitters.com)
A classic combat boot is all you need to trek through the weekend.
Stand Studio Maria Cocoon Oversized Faux Shearling Coat ($228; net-a-porter.com)
A warm, plush teddy coat is pretty much a must-have this season.
More is More
Whoever said “less is more” was totally wrong—well, at least when it comes to leather. “Match your leather pants with a leather jacket for a biker chic vibe, and add a scarf or bandana to complete the look,” suggests Zyla.
Wear the look:
Commando Control Top Faux Patent Leather Leggings ($98; nordstrom.com)
Want to truly shine this winter? Then a pair of patent leather pants is exactly what you need in your wardrobe.
Jakett Adrienne Jacket ($400; freepeople.com)
This light pink jacket is a great way to play with color if you’re not into the monochromatic look. Leather pockets add to the leather-on-leather effect.
Susanna Scarf ($58; anthropologie.com)
If you’d rather add just a subtle touch of color, this patchwork scarf can do the trick.
Comfy and Cozy
If you want to stay stylish and cozy during below-freezing temps, Zyla recommends styling your leather pants with an oversized chunky sweater. “Add some edge with a hi-lo or asymmetrical hem,” he says.
N:Philanthropy Scarlett Leather Jogger ($248; revolve.com)
These leather pants are just as comfy as your favorite sweatpants.
ModCloth On and Soft Again Chenille Sweater ($55; modcloth.com)
A soft chenille sweater is great for a trending look while staying cozy during the winter weather.
Caslon Mock Neck High Low Sweater ($42; nordstrom.com)
Play up your turtleneck sweaters with this high-low hemline.
Layered Up
“Winter is all about layering so don’t forget to add a layer of leather to your outfit by wearing leather leggings under your favorite all-season dress,” says Kosich. “You are sure to be remembered as a style maker with this look.”
Vince Camuto Snake-Embossed Leggings ($79; bloomingdales.com)
Add some texture to your outfit with this snake-print leather pant.
American Apparel 50/50 Ringer T-Shirt Dress ($15; americanapparel.com)
If you’re looking for a casual approach, try pairing your leather pants with your favorite t-shirt dress.
Madewell Indigo Ruffle-Neck Smocked Babydoll Dress ($128; madewell.com)
Or, give your go-to babydoll an edge with a pair of leather pants.
Color Pop
If you want just a touch of color, go for the all-black outfit and let your shoes take the spotlight. “For a night out, team a sleek pair of leather pants with a fitted knit top in the same color and a pair of vividly-hued stilettos,” says Zyla.
Spanx Faux Leather Moto Leggings ($110; nordstrom.com)
Give your #ootd a biker-influenced edge with this moto leather legging.
UO Sabel Textured Wrap Top ($39; urbanoutfitters.com)
This ballet-inspired top will give your grungiest outfits a femme vibe.
Aldo Cassedy High Heel Stiletto ($90; aldo.com)
A punchy red heel can do wonders for an all-black outfit.
Travel Essentials
“Leather is super comfortable and easy to travel in, so wear with a cashmere sweater and driving moccasins for that long flight,” says Kosich. “Then, mix and match with dressy and casual separates to complete your travel wardrobe.”
Aritzia Wilfred Free Modern Cargo Pant ($148; aritzia.com)
Want to look stylish while letting your legs breathe on a long flight? Enter: the cargo fit.
Charter Club Ribbed Colorblocked Cashmere Sweater ($95; macys.com)
Even if the temperature is currently below-40 degrees, embody the warm joy of springtime with some fun pastels.
L.L. Bean Women’s Wicked Good Moccasins ($79; llbean.com)
Keep your toes comfy and warm during your travels with these under-$100 shearling-lined moccasins.
"We often receive complimentary products to review at WellSquad. Each product we feature has been independently selected and reviewed by our editorial team."