High Rise Bootcut Pants

Step into your power with high rise bootcut pants that are ready to strut their stuff and take you from day to night in style. These wardrobe essentials are all about that perfect blend of classic charm and modern flair, giving you the confidence to own any room. Whether you're channeling those boss babe vibes at work or dancing the night away with your squad, these pants have your back. Pair them with your fave tops and killer heels for a look that's effortlessly chic and totally unstoppable. Get ready to turn heads and break hearts—because when you're rocking high rise bootcut pants, there's no stopping you!

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Windsor So Far So Good High-Rise Bootcut Denim Jeans in Dark Denim

$44.90

A pair of dark denim high-rise bootcut jeans with a slim fit and slight stretch for comfort.

Windsor Trendsetter Alert Coated Faux Leather Flared Pants in Brown

$39.90

A stylish pair of brown faux leather flared pants with a high-rise waist and sleek fit.

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.

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.

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 finish.

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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

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

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: 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

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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: S | 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

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

High Rise Bootcut Pants

High rise bootcut pants are the ultimate closet chameleons—effortlessly blending timeless style with modern-day versatility. When winter rolls in and outfit inspiration starts to feel as gray as the sky, these pants step up as a reliable foundation for just about any look you’re dreaming up. That high-rise waistband isn’t just about following a trend; it’s about comfort, coverage, and that magical waist-defining effect that works for so many body types. Whether you’re curvy, athletic, or somewhere in between, the bootcut silhouette offers a subtle flare that balances proportions and flatters from every angle. Think of them as your personal stylist’s secret weapon: elongating your legs, smoothing your shape, and giving you that “I just threw this on” confidence without a second thought. And because bootcut pants come in everything from classic denim to structured twill and even bold bootcut pants print options, you can switch up your vibe as easily as you swap your shoes.

Styling high rise bootcut pants is an exercise in creativity—layer them with chunky knits and ankle boots for a cozy December brunch, or pair them with a sleek turtleneck and heeled booties for a night out that calls for a little extra polish. If you’re gifting, these pants are a smart pick for anyone who loves pieces that can go from work meetings to weekend plans without skipping a beat. They’re especially thoughtful for friends or family who appreciate a flattering fit but don’t want to sacrifice comfort (because, let’s be honest, we all have those days when only a high-rise will do). For the office, a tailored bootcut pant in a neutral hue instantly elevates your look, while a bootcut pants print or bold color can add just enough personality to keep things interesting. And if you’re shopping for yourself, think of high rise bootcut pants as the answer to your “I have nothing to wear” mornings—they’re just as at home with sneakers and a vintage tee as they are with a blazer and pumps.

Fit is everything when it comes to making the most of this silhouette. Look for a waistband that sits comfortably at your natural waist, and pay attention to the length—just grazing the top of your shoe is the sweet spot for that leg-lengthening effect. If you’re on the petite side, a slightly shorter inseam or a heeled boot can help prevent fabric from pooling at the ankle. For those who love to experiment, try mixing textures (think denim with a ribbed knit or faux leather with a silky blouse) or layering with unexpected accessories. And if you’re looking to expand your style repertoire even further, don’t miss the chance to explore complementary silhouettes like High Rise Flare Pants, which offer a little extra drama while keeping that same waist-cinching magic. However you style them, high rise bootcut pants are proof that the right pair of pants can turn even the simplest outfit into a moment—no overthinking required.

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