Fall Trousers

Get ready to strut your stuff in the ultimate fall trousers that are about to become your new seasonal obsession. Picture this: crisp autumn air, leaves crunching underfoot, and you, turning heads with every step in those effortlessly chic pants. Whether you're channeling cozy vibes for a pumpkin patch date or serving up some serious office glam, these trousers are your go-to for all things fabulous this fall. With styles that range from tailored classics to laid-back cool, you’ll find the perfect pair to match your mood—and maybe even make a few jaws drop along the way. So, let’s dive into fall with trousers that promise to keep you looking fierce and feeling unstoppable!

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Windsor Classic And Chic Wide-Leg Trouser Pants in Black

$35.90

A chic black ponte knit trouser with a high-rise waist and flattering wide-leg silhouette.

Windsor Nine To Five Straight-Leg Crepe Trouser Pants in Black

$34.90

A stylish black crepe trouser with a high-rise waist and straight-leg silhouette for workwear.

Windsor Sleek Business High-Rise Faux Leather Flare Pants in Black

$39.90

A pair of black faux leather high-rise flare pants with a hip-hugging fit and sleek style.

Best Seller

High-Rise Coated Skinny Pants in Black

$39.90

A chic pair of high-rise black skinny pants in coated faux leather with minimal stretch.

Walking The Walk Faux Leather Straight Leg Pants in Black

Best Seller

Walking The Walk Faux Leather Straight Leg Pants in Black

$39.90

A sleek pair of black faux leather pants with a high-rise waist and straight-leg silhouette.

Out For The Day High-Rise Cargo Pants in Brown

$42.90

A stylish pair of brown high-rise cargo pants with adjustable drawcord hems and multiple pockets.

Trendsetter Alert Coated Faux Leather Flared Pants in Brown

$39.90

A chic brown faux leather pant with a high-rise waist and flared hem for trendsetting style.

Now Trending

High-Rise Coated Skinny Pants in Black

$39.90

(117)

Elevate your wardrobe with these essential pair of faux leather pants! These chic coated skinny pants feature a high-waist fit, waistband with belt loops, two back pockets, and hidden zipper closure. Style these high-rise pants with a sleek mesh bodysuit, corset top, or blouse for a chic and fierce look. Fit & FeaturesHigh-rise waist, belt loops, Front button and hidden zipper closure, Faux front pockets, two back pockets, Skinny leg design, Coated faux leather fabric, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor High-Rise Coated Skinny Pants in Black | Size: S | Leather

Walking The Walk Faux Leather Straight Leg Pants in Black

$39.90

(23)

In these faux leather pants, you'll be walking the walk of cool-effortless style! They feature a flattering high-rise waist and straight-leg silhouette on coated faux leather fabric that offers a sleek look for workwear or everyday 'fits. Complete the look in a smooth bodysuit and block heels. Fit & FeaturesHigh-rise waist, Straight-leg silhouette, Front button and hidden zipper closure, Faux front pockets, functional back pockets, Coated faux leather fabric, slight stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Walking The Walk Faux Leather Straight Leg Pants in Black | Size: M

Forever On Trend High Rise Ponte Capri Pants in Black

$28.90

(20)

Slip into these classic and chic ponte capri pants for effortless style! Channel a 90s vibe in these pants featuring a flattering high-rise waist, form-hugging fit, and flirty side slit accents along the hem. Complete the look in a basic tee and sandals! Fit & FeaturesPonte knit fabric, minimal stretch, High-rise waist, Form-hugging fit, Side slit accents, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Forever On Trend High Rise Ponte Capri Pants in Black | Size: XS | Knit Fabric

Classic And Chic Wide-Leg Trouser Pants in Black

$35.90

(19)

These classic and chic ponte knit trouser pants feature a high-rise elasticized waist with a hip-hugging fit and a wide-leg hem. The vertical seam running down the front of each leg will create a flattering silhouette you'll love. Fit & FeaturesPonte knit fabric with moderate stretch, High-rise elasticized waist, Vertical front seams, Hip-hugging fit, Wide-leg silhouette, Pants in size small have an 11" front rise with a 31" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Classic And Chic Wide-Leg Trouser Pants in Black | Size: S | Knit Fabric

Windsor Nine To Five Straight-Leg Crepe Trouser Pants in Black

$34.90

(13)

Look stylish and posh for your nine-to-five in these crepe trouser pants! Designed with a flattering high-rise waist and front pin-tuck detailing going down the straight-leg silhouette, you'll feel so confident to take on the day. Complete the look in an oversized blazer and heels. Fit & FeaturesCrepe fabric with stretch, High-rise waist, Pull-on-and-off styling, Straight-leg silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Nine To Five Straight-Leg Crepe Trouser Pants in Black | Size: L

Sleek Business High-Rise Faux Leather Flare Pants in Black

$39.90

(7)

These faux leather pants feature a flattering high-rise waist, hip-hugging fit, and a trendy flare hem on coated fabric for a sleek look. Perfect for styling with a graphic tee and booties. Fit & FeaturesCoated faux leather fabric, slight stretch, High-rise waist, Hip-hugging fit, flare hem, Front button and hidden zipper closure, Two-pocket styling, Pants have an 11" front rise with a 30.5" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Business High-Rise Faux Leather Flare Pants in Black | Size: XS

Windsor Sleek Polish High-Rise Flare Trouser Pants in Black

$42.90

(7)

Sleek, sculpted, and made to move with you. These high-waist flare pants blend polished tailoring with a flattering seam detail—perfect for dressing up your 9-to-5 or elevating your weekend look. Fit & FeaturesSmooth woven fabric, High-rise waist, belt loop accents, Hidden front zipper and hook-eye fasteners, Hip-hugging fit, Seam detailing down the front, Flare hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Polish High-Rise Flare Trouser Pants in Black | Size: L | Woven Fabric

Sale

Sleek Look Mid-Rise Cutout Flare Pants in Black

$16.97 $39.90
57% off

(4)

Perfect for hangouts or dinners out, these mid-rise flare pants accentuate your best assets! With a flirty side waist cutout with adjustable drawstring and a hip-hugging fit, these pants offer a sleek look. Fit & FeaturesSlinky knit fabric, full knit stretchy lining, Mid-rise waist, Side waist cutout with adjustable drawstring, Hip-hugging fit, Flare hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Look Mid-Rise Cutout Flare Pants in Black | Size: L | Knit Fabric

Windsor Chic And Confident Pinstripe Flared Trouser Pants in Black

$46.90

(3)

Sharp lines, chic confidence. These pinstripe trouser pants hug through the hips, flare out at the hem, and instantly pull an outfit together whether you’re dressing them up or keeping it low-key. Style with the matching vest top! Shop Matching Vest: Chic And Confident Pinstripe VestFit & FeaturesPinstripe print, Knit fabric, Low-rise waistband with belt loops, Slim fit through hip and thigh, Flared leg silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic And Confident Pinstripe Flared Trouser Pants in Black | Size: L

Glitzy Vibes Rhinestone Knit Flare Pants in Black

$49.90

(2)

You'll be the first star everyone sees at the party in these glitzy high-rise pants! With all-over tonal rhinestones, a hip-hugging fit, and a flare hem, these pants will make an entrance. Fit & FeaturesKnit fabric, All-over tonal rhinestone embellishments, High-rise waist, Hip-hugging fit, Form-hugging fit through the legs, Flared hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Glitzy Vibes Rhinestone Knit Flare Pants in Black | Size: M

Fall Trousers

There’s something about fall that makes pulling on a great pair of trousers feel like a ritual—one that signals the return of crisp mornings, golden afternoons, and that sweet spot between bundled-up and breezy. This is the season where your wardrobe starts to work overtime, and trousers step up as the unsung heroes of getting dressed. Think about it: whether you’re dashing out the door with coffee in hand, settling into a corner booth for Sunday brunch, or powering through back-to-back meetings, a well-chosen pair of fall trousers instantly elevates your look and your mood. They’re the piece that bridges the gap between comfort and polish, giving you room to move (and breathe) without sacrificing an ounce of style. The best part? Trousers work for everyone—students, professionals, creatives, and anyone who wants to look put-together with minimal effort. They’re also a thoughtful gift for the friend who’s always “borrowing” your clothes, the sister who’s starting her first job, or the roommate who’s on a mission to upgrade her closet. Trousers are that rare find: practical, versatile, and always in style, no matter how much your taste or schedule changes.

When it comes to picking out fall trousers, it’s all about finding the right balance between trend and timelessness. This season, look for rich textures—think soft suiting, subtle plaids, or a hint of stretch that lets you move through your day with ease. The silhouette is key: wide-leg trousers bring a little drama and look incredible with an oversized sweater, while tailored styles can be dressed up or down depending on your mood (or your calendar). And don’t sleep on details like pleats, high waists, or unexpected colors—these are the small touches that make your outfit feel intentional, even if you got ready in five minutes flat. Layer them with chunky knits, cropped jackets, or a sleek bodysuit for endless combinations that feel fresh every time. If you’re shopping for someone else, trousers are a safe bet for anyone who loves to mix and match, experiment with new looks, or just needs a reliable go-to for everything from class to cocktails. They’re the silent staple that quietly makes every closet better, season after season.

As you refresh your fall wardrobe, remember that good trousers are an investment in feeling confident and comfortable, no matter what the day throws at you. They’re the foundation for those “I actually have my life together” moments—even if you’re just making a grocery run in the rain. If you’re ready to explore more options, take a look at our curated collection of Contemporary Trousers for styles that blend modern edge with everyday wearability. Whether you’re building a capsule closet or just looking for that one perfect pair, fall trousers are the starting point for outfits that work as hard as you do.

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