High Waist Casual Pants
High waist casual pants are the ultimate wardrobe MVPs for our Windsor girl ready to slay the day with style and confidence. Perfect for any occasion, these pants effortlessly blend comfort with a chic vibe, making them your go-to choice whether you're brunching with the squad or owning the office. With a flattering fit that highlights your silhouette and endless styling possibilities, these pants are your fashion-forward partner in crime. So go ahead, strut your stuff and let those high waist casual pants do all the talking.
$46.90 - $49.90
A chic black cargo jogger with high-waist, metal ring trims, and elastic hem for a sporty look.
$32.90
A chic pair of high-rise black skinny pants in coated faux leather with minimal stretch.
$42.90
A pair of medium denim high-rise mom jeans with distressed knee slits and a skinny leg fit.
$49.90
A pair of black high-rise cargo denim jeans with a straight-leg silhouette and trendy flap pockets.
$35.90
A chic ivory trouser with a high-rise waist and flattering wide-leg silhouette.
$46.90
A stylish pair of medium denim jeans with a high-rise waist and trendy knee destruction accents.
$34.90
A sleek pair of black faux leather pants with a high-rise waist and straight-leg silhouette.
$44.90
A pair of black high-rise cargo pants with cotton twill-knit fabric and multiple pockets.
$34.90
A stylish black crepe trouser with a high-rise waist and straight-leg silhouette for workwear.
$42.90
A stylish pair of brown high-rise cargo pants with adjustable drawcord hems and multiple pockets.
$34.90
A chic pair of black faux leather pants with a high-rise waist and trendy flare hem.
$28.90
A chic pair of black ponte capri pants with a high-rise waist and flirty side slits.
$44.90
A chic pair of black chiffon palazzo pants featuring a high-rise waist and wide-leg pleats.
$46.90
A medium-wash, high-rise denim jean with a wide-leg flare and hip-hugging fit.
$42.90
A pair of charcoal high-rise cargo pants with nylon woven fabric and adjustable bungee drawcord hems.
$32.90
A high-rise sage crepe trouser with a flattering wide-leg silhouette for a polished look.
$49.90
A cognac satin jogger pant with a high-rise waist, cargo pockets, and adjustable drawcord cuffs.
$34.90
A stylish pair of brown faux leather flared pants with a high-rise waist and sleek fit.
$46.90
A pair of high-rise boyfriend jeans in denim with distressed accents and a cuffed hem.
$34.90
A chic pair of ivory crepe trousers featuring a high-rise waist and straight-leg silhouette.
$9.97 $36.90 73% off
A high-rise brown faux leather pant with a lace-up front and flared hem for sleek style.
$49.90
A stylish pair of high-rise denim cargo jeans featuring a straight-leg silhouette and eight-pocket design.
$27.90
A chic pair of black and white gingham capri pants with a high-rise waist and side slits.
$49.90
A pair of black knit flare pants with all-over rhinestone embellishments and a high-rise waist.
$39.90
A sophisticated pair of black ponte knit pants featuring a belted waist and tapered straight leg.
$42.90
A chic pair of rose high-rise trouser pants with a flattering wide-leg silhouette and side pockets.
$34.90
A sleek black crepe knit trouser with a high-rise belted waist and straight-leg fit.
$13.97 $32.90 58% off
A pair of camel faux suede pants featuring dual lace-ups and a stylish flared hem.
$26.90
A sleek 90s-inspired high-rise capri pant in black woven fabric with a form-hugging fit.
$32.90
A comfy black ponte knit pant with a high-rise waist and flared hem for versatile styling.
$29.90
A boho chic black sheer lace flare pant with a high-rise elastic waist and knit lining.
$29.90
A playful pink pajama pant with cherry print, featuring a lace-trimmed high-rise waist and relaxed flare hem.
$44.90
A stylish pair of khaki high-rise cargo pants with a straight-leg fit and six-pocket design.
$36.90
A chic pair of snake print flare pants with clear sequin embellishments and a high-rise waist.
$32.90
A trendy pair of brown faux suede flare pants with a high-rise waist and leopard print.
$34.90
A high-rise taupe ponte pant with a flare leg silhouette and stretchy knit fabric.
$9.97 $29.90 67% off
A brown high-rise knit flare pant with a fold-over waist and ribbed hacci fabric for comfort.
$29.90
A pair of black crochet lace flare pants with a high-rise waist and hip-hugging fit.
$46.90
A trendy medium denim with high-rise waist and destructed detailing for a chic, casual look.
$18.97 $44.90 58% off
A high-rise dark denim bootcut jean with moderate stretch and vertical front seam accents.
$46.90
A light denim high-rise jean with unique seam detailing and a trendy flare hem.
$46.90
A dark denim high-rise jean with a hip-hugging fit and stylish flare hem.
$44.90
A pair of black high-rise acid wash cargo jeans with a slight stretch and straight-leg hem.
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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: M | Leather
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 Ivory | Size: XS | Knit Fabric
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: L
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: XS
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
Feel the breeze on the weekend in these crochet palazzo pants at festivals, concerts, or out at the fair! Featuring a high-rise elasticized waistband and a wide-leg silhouette, these pants offer a flattering fit on crochet fabric lined with stretch knit. Complete the look in a crop top. Fit & FeaturesCrochet fabric lined with stretch knit, High-rise elasticized waistband, Wide-leg silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Weekend Breeze High-Rise Crochet Palazzo Pants in Denim | Size: L
Pretty pleats make these high-rise palazzo pants a chic find! Style with a crop top and heels for dinner and drinks. Fit & FeaturesChiffon woven fabric, knit lining, High-rise waist, Wide-leg pleated silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Pretty Pleats High-Rise Chiffon Palazzo Pants in Natural | Size: M | Chiffon/Knit Fabric/Woven Fabric
Spice things up in these sleek and trendy faux leather pants, which boast fringed side trim and a flattering flare hem—perfect for dancing at festivals or concerts! Fit & FeaturesFaux leather lined fabric, minimal stretch, Mid-rise waist, front button and hidden zipper closure, Faux front pockets, back pockets, belt loops, Hip-hugging fit, Fringed side trim, Flare hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Spicing Things Up Mid-Rise Flare Fringe Pants in Black | Size: 3 | Leather
A comfy and cute mid-rise flare pants perfect for post-pilates and grabbing coffee! Pair with the matching jacket. Fit & FeaturesStretchy rib knit fabric, Folded mid-rise waist, Hip-hugging fit, Flare hem, Runs true to size, Shop The Matching Jacket: At Your Leisure Zip-Up Crop Jacket Free Shipping on All Orders Over $75. | Windsor At Your Leisure Mid-Rise Flare Pants in Black | Size: S | Knit Fabric
A perfectly trendy pair of denim pants with cute details like a pinstripe pattern and flattering wide-leg silhouette. Complete the look with the matching vest. Shop Matching Vest: Fresh Perfection Button Split Denim VestFit & FeaturesPinstripe pattern, denim fabric, High-rise waist, Wide-leg silhouette, Front button and hidden zipper closure, Four-pocket styling , Runs true to size , Free Shipping on All Orders Over $75. | Windsor Fresh Perfection High-Rise Wide-Leg Denim Pants in Dark Denim | Size: M
High Waist Casual Pants
Let’s be real: there’s something about high waisted casual pants that just hits different. Whether you’re running errands with your besties, heading to that brunch spot everyone’s talking about, or just living your main character moment on campus, high waisted casual pants are the ride-or-die staple your closet’s been dreaming of. They’re the ultimate confidence booster—snatching your waist, elongating your legs, and making even the laziest days look put together. Slide into a pair and suddenly you’re strutting, not walking, and every mirror you pass is an opportunity for a quick selfie. It’s the kind of energy that says, “Yeah, I woke up like this—and I’m not apologizing for it.” High waisted casual pants are that magical blend of comfort and style, giving you the freedom to move, dance, and conquer your day without ever sacrificing your vibe. Whether you’re pairing them with a cropped tee for that effortlessly cool look or going full boss mode with a blazer and statement heels, these pants are the MVPs of versatility.
Gift shopping for your fashion-forward bestie? High waisted casual pants are a guaranteed crowd-pleaser. They’re the piece that fits seamlessly into every wardrobe, no matter her style—edgy, preppy, boho, or somewhere in between. Imagine gifting a pair to your sister for her first big interview or to your BFF for her birthday bash—she’ll be texting you nonstop about how obsessed she is. These pants are made for making memories, whether it’s late-night adventures, spontaneous road trips, or just vibing at home with your crew. They’re also the unsung heroes of transitional dressing; throw on some sneakers for a coffee run or swap in chunky boots when you’re feeling extra. And if you want to take your look to the next level, don’t sleep on the power of a high waist in a classic hue. For those moments when you want to channel pure sophistication, check out our Black High Waist Pants—they’re the definition of timeless.
Here’s the inside scoop: when you’re shopping for high waisted casual pants, it’s all about finding your perfect fit and fabric. Think soft, stretchy materials that move with you, pockets deep enough for your phone (and maybe that emergency lip gloss), and details like pleats, tie waists, or cute buttons that make your look pop. Go for bold prints when you’re feeling playful or classic neutrals for that wear-anywhere appeal. And don’t forget—these pants are made for mixing and matching, so you can keep your style fresh without overthinking it. Whether you’re dressing up for a night out or just want to look cute while chilling at home, high waisted casual pants are your ticket to feeling like the main character every single day.