Stretch Flare Pants

Stretch flare pants are the ultimate game-changer for your wardrobe, combining timeless flair with modern comfort. These pants are your go-to for those days when you want to strut your stuff with confidence and a touch of retro chic. Whether you're heading to brunch with the squad or dancing the night away, these fabulous flares will have you moving and grooving in style. So, slip into a pair of stretch flare pants and let them work their magic—because life's too short for boring outfits!

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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 sleek high-rise brown faux leather pant with a flattering straight-leg fit and flared hem.

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.

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.

Make A Scene Mid-Rise Flare Denim Jeans in Dark Denim

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Make A Scene Mid-Rise Flare Denim Jeans in Dark Denim

$49.90

A pair of dark denim mid-rise flare jeans with seam detailing and a hip-hugging fit.

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.

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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

Stretch Flare Pants

Stretch flare pants are the quiet MVPs of a modern closet—always ready to flex (literally and figuratively) when you need an outfit that feels as good as it looks. Whether you’re navigating a packed day of classes, heading to the office, or plotting a last-minute dinner with friends, these pants are the definition of effortless polish. The magic is in the fabric: think soft, forgiving, and just the right amount of hug. That built-in stretch means you can actually move—no stiff waistband, no awkward tugging, just pure comfort from morning coffee runs to late-night plans. And let’s talk silhouettes: the flare adds instant drama (the good kind), elongating your legs and giving every step a little extra swish. For anyone who’s ever wanted to channel that retro-cool vibe without feeling like you’re in costume, stretchy flare pants are your low-key ticket. They’re the rare piece that works for all body types, balancing curves and adding shape where you want it most. It’s no wonder they’re a go-to for gifting, too—because who doesn’t appreciate a pant that actually fits and flatters?

As the days get shorter and the air turns crisp, there’s something about slipping into bell bottom stretch pants that just feels right. Picture this: you’re layering up for a chilly morning, wrapping yourself in a chunky knit, and pulling on a pair of black stretchy flare pants that instantly elevate the whole look. They’re the answer to “what do I wear?” when you’re tired of jeans but still want structure, or when leggings feel a little too casual but you refuse to compromise on comfort. For holiday parties, Friendsgiving gatherings, or even just cozy nights in, elastic flare trousers can be styled up or down with zero fuss. Swap in a silky cami and heels for a night out, or keep it casual with sneakers and an oversized sweater. They’re also a dream for travel—easy to pack, wrinkle-resistant, and always ready to go the distance (even if your plans are just a quick coffee run and some window shopping). If you’re shopping for someone else, stretchy flare pants are a thoughtful pick. They’re forgiving in fit, versatile in style, and guaranteed to be worn on repeat—perfect for sisters, besties, or anyone who deserves a little upgrade to their daily rotation.

The beauty of flare stretch pants is in their versatility. They’re not just for one vibe or one season—they flex with your mood, your plans, and your personal style. If you’re into clean lines and a tailored finish, elastic flare trousers can be paired with a crisp button-down for a look that’s all business (without feeling buttoned-up). More of a free spirit? Lean into the boho energy with a flowy blouse and chunky boots. And if you’re chasing that model-off-duty look, black stretchy flare pants and a fitted turtleneck are a foolproof combo. From brunch to boardroom, errands to evenings out, these pants are the definition of “throw on and go.” If you’re craving more ways to play with proportions and find your perfect fit, take a peek at our curated collection of Fitted Flare Pants for even more inspo. No matter how you style them, stretch flare pants are the wardrobe staple you’ll reach for again and again—because feeling confident, comfortable, and put-together shouldn’t be a rare occasion.

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