Womens High Rise Flare Pants

Ready to serve main character energy? Women’s high rise flare pants are here to make every sidewalk your runway. With a nod to retro vibes and a dash of modern sass, these pants are made for the girl who loves to turn heads and break hearts. Whether you're dressing them up for a night out or keeping it chill for brunch with the squad, these flares bring that instant confidence boost you crave. Go ahead, strut your stuff—your new favorite pair is waiting.

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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 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.

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.

Sultry Boho Crochet Lace Flare Pants in Black

$29.90

A pair of black crochet lace flare pants with a high-rise waist and hip-hugging fit.

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High-Rise Coated Skinny Pants in Black

$39.90

(119)

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

(32)

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

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: S | Knit Fabric

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

$34.90

(14)

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

Retro Remix Striped Flare Pants in Brown

$39.90

(8)

Retro flair meets everyday comfort. These striped flare pants sculpt your shape with a soft stretch fit that’s equal parts chill and elevated—perfect for coffee runs, office hours, or casual nights out. Fit & FeaturesStriped print, stretch knit fabric, Smooth high-rise waist, Hip-hugging fit, Flared hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Retro Remix Striped Flare Pants in Brown | Size: L | Knit 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 Trendsetter Alert Coated Faux Leather Flared Pants in Brown

$39.90

(4)

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: L

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

Womens High Rise Flare Pants

High rise flare pants are the kind of closet staple that quietly does the heavy lifting, no matter what your calendar looks like. They’re the unsung heroes of winter layering—the ones you reach for when you want to look instantly put together, but still need to feel like yourself. There’s something about the way a high rise cut smooths and elongates, giving you that legs-for-days effect without the fuss of a full-on wide leg. Whether you’re navigating chilly January mornings, running from class to coffee, or just want a break from your usual denim rotation, high rise flares have you covered. They sit comfortably at your natural waist, which means no awkward tugging or adjusting throughout the day, and they pair just as well with chunky knits as they do with cropped jackets or your favorite bodysuit. If you’ve ever found yourself in that “what do I even wear to this?” spiral, these pants are the shortcut to an outfit that feels both effortless and elevated. Plus, they’re a dream for showing off your go-to boots or that pair of platforms you’ve been saving for a night out.

Shopping for high rise flare pants isn’t just about chasing a trend—it’s about finding a fit that works for your lifestyle and your mood. Maybe you’re gifting a pair to your best friend who’s always mixing up her style, or maybe you’re treating yourself to a little January wardrobe reset (because yes, new year, new fits is a real thing). High rise flares make a thoughtful gift for anyone who loves a vintage-inspired silhouette, needs a work-to-weekend option, or just appreciates a pant that can handle both brunch and a boardroom. Look for soft, stretchy fabrics if comfort is your top priority, or go for structured styles if you want a little more polish. Dark washes and classic neutrals are perfect for winter, but don’t sleep on bold colors or subtle patterns if you’re after something that stands out. And if you’re curious about mixing it up, there’s always the option to compare with other rises—check out our Mid Rise Flare Pants for a slightly different vibe that still delivers on style.

Styling high rise flare pants really is as easy as it looks—think oversized scarves, sleek turtlenecks, or even a statement belt to emphasize that waistline. They’re versatile enough to go from a casual coffee run to a last-minute dinner invite, and they photograph beautifully (trust us, your mirror selfies will thank you). If you’re layering up for the cold, try a fitted thermal or long sleeve tucked in, then add a tailored coat or puffer for warmth that doesn’t sacrifice style. And when spring finally rolls around, just swap your boots for sandals and you’re set. High rise flares are one of those rare finds that work for every body type, every occasion, and every season—making them the ultimate investment piece for anyone who wants to look and feel their best, without overthinking it. Whether you’re shopping for yourself or picking out a gift that’s guaranteed to be worn on repeat, these pants are proof that fashion can be both fun and functional, all winter long and well beyond.

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