Leisure Pants

Leisure pants are the ultimate wardrobe MVP, ready to take you from lazy Sunday brunches to spontaneous road trips with the squad. These chic and comfy bottoms are your go-to for mixing effortless style with a sprinkle of sass. Whether you're lounging at home or hitting the town, leisure pants have got your back, making sure you feel fabulous and free to slay the day your way. So, slip into these versatile wonders and let the good times roll!

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Windsor Major Cutie Cargo Joggers Pant in Black

$46.90

A chic black cargo jogger with high-rise waist, metal ring trims, and elastic cuffed hems.

Forever On Trend High Rise Ponte Capri Pants in Black

Best Seller

Forever On Trend High Rise Ponte Capri Pants in Black

$28.90

A chic pair of black ponte capri pants with a high-rise waist and flirty side slits.

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.

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.

Windsor Glitzy Vibes Rhinestone Knit Flare Pants in Black

$49.90

A pair of black knit flare pants with all-over rhinestone embellishments and a high-rise waist.

Now Trending

High-Rise Coated Skinny Pants in Black

$39.90

(118)

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

Forever On Trend High Rise Ponte Capri Pants in Brown

$28.90

(27)

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 Brown | Size: M | Knit Fabric

Walking The Walk Faux Leather Straight Leg Pants in Black

$39.90

(24)

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

Windsor Classic And Chic Wide-Leg Trouser Pants in Black

$35.90

(20)

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: XS | 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 Polish High-Rise Flare Trouser Pants in Black

$42.90

(9)

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: S | Woven Fabric

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 Chic And Confident Pinstripe Flared Trouser Pants in Black

$46.90

(4)

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

Windsor Trendsetter Alert Coated Faux Leather Flared Pants in Brown

$39.90

(3)

Set the trends in this coated faux leather flare pant featuring a sleek high-rise waist and a flattering straight-leg fit that flares out at the hem. Pair with a long sleeve top. Fit & FeaturesCoated faux leather fabrication, High-rise waist, Single button with hidden zipper closure, Straight-leg fit, Flared hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Trendsetter Alert Coated Faux Leather Flared Pants in Brown | Size: XS

Windsor Low Effort Tie Waist Flare Pants in Black

$34.90

(3)

Low effort, high payoff—these pants do all the talking. The sleek flare pants shape with a soft tie detail create an easy, flattering fit that works for nights out, dinner plans, or styled up with a bandeau. Fit & FeaturesKnit stretch fabric, Low-rise tie waist design, Hip-hugging fit, Flared hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Low Effort Tie Waist Flare Pants in Black | Size: XS

Leisure Pants

Leisure pants are the unsung heroes of every wardrobe—equal parts comfort and style, designed to move with you from lazy mornings to spontaneous coffee runs and everything in between. When you’re shopping for pants Windsor style, it’s all about finding that perfect blend of softness, stretch, and silhouette that feels as good as it looks. Think: elastic waistbands that never dig in, buttery fabrics that drape just right, and fits that let you breathe (literally and figuratively). Whether you’re a homebody who loves a cozy movie marathon or someone who lives for a long walk in the crisp February air, leisure pants have you covered. They’re the pieces you reach for when you want to look put-together without even trying—ideal for Zoom calls, brunch dates, or a quick dash to the market. And if you’re thinking about gifting, trust us: leisure pants are a crowd-pleaser. They work for your best friend who’s always on the go, your sister who’s got a knack for loungewear chic, or even Mom, who deserves a little extra comfort. No sizing guesswork, no worrying about style misfires—just pure, wearable ease.

The beauty of leisure pants is in their versatility. Go classic with a straight leg for a streamlined look that pairs with everything from oversized sweaters to cropped tanks, or embrace the laid-back vibe with wide-leg and jogger styles that bring a dose of street-style energy to your everyday. If you’re craving a little nostalgia, flare silhouettes are back in a big way—flattering, elongating, and just the right amount of retro. For those who run hot, lightweight cotton or modal blends keep things breezy, while plush knits and fleece-lined options are your February best friends, especially when the weather calls for layering up. Don’t underestimate the power of pockets, either—perfect for stashing your phone, keys, or that emergency lip balm. And when it comes to color, you can’t go wrong with neutrals for maximum mix-and-match potential, but a pop of pastel or a bold print can instantly lift your mood (and your outfit). If you’re already dreaming of warmer days, keep an eye on transitional styles that work now and later—think cropped hems or breathable fabrics that will segue seamlessly into spring. For even more inspiration, check out our Summer Pants collection and start planning your next seasonal switch-up.

Ultimately, leisure pants are about celebrating your downtime—and your downtime deserves to look and feel amazing. They’re the answer to “I have nothing to wear” days, the solution for travel comfort without sacrificing style, and the secret weapon for anyone who wants to blur the line between loungewear and streetwear. With pants Windsor knows how to do best, you get the freedom to style them your way: dressed up with a blazer and sneakers, dressed down with a hoodie and slides, or styled somewhere in between. The best part? You don’t have to choose between comfort and confidence—you get both, every single time. So whether you’re shopping for yourself, curating a care package, or simply refreshing your rotation for the season ahead, leisure pants are the ultimate foundation for effortless, everyday style.

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