Casual Flare Pants

Get ready to strut your stuff in casual flare pants that scream effortless chic and endless confidence. These wardrobe wonders are the ultimate go-to for any Windsor girl who’s ready to rock her day with a touch of flair. Whether you're brunching with the squad or owning the dance floor, these pants have got your back, hugging you in all the right places while flaring out for that perfect silhouette. Pair them with your fave top and some killer accessories, and you've got a look that's as unstoppable as you are!

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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.

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.

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.

Sheer Fling Lace Flare Pants in Ivory

$29.90

A pair of romantic ivory sheer lace flare pants perfect for making a statement at festivals.

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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 Black

$28.90

(33)

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: XS | 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

Windsor 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: L | 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

Windsor 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: S

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: M

Windsor Lounge Goals Rib Knit Flare Pants in Black

$39.90

(3)

Made for slow mornings and casual weekend plans, these rib knit flares keep you comfy but styled. The foldover waistband and side drawstrings let you adjust the vibe from relaxed to snatched. Fit & FeaturesRib knit fabric with stretch, High-rise foldover waistband, adjustable side drawstrings, Hip-hugging fit, Flare hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Lounge Goals Rib Knit Flare Pants in Black | Size: XS | Knit Fabric

Casual Flare Pants

Casual flare pants are the low-key heroes of every closet—effortlessly cool, endlessly versatile, and just structured enough to make you feel like you have your life together (even if you hit snooze three times and skipped breakfast). Whether you’re running errands, grabbing coffee with friends, or heading to a casual office, a great pair of flares instantly elevates even the simplest tee or sweater. February’s unpredictable weather is basically begging for pieces that can flex with your plans and your mood, and flare pants do just that. Picture them with a cozy knit and chunky sneakers for a laid-back weekend, or swap in a fitted top and heeled boots for a dinner date that doesn’t feel try-hard. There’s something about that subtle kick at the hem that brings a little drama to your everyday without a hint of discomfort—perfect for when you want to look like you tried, but not too hard.

When it comes to picking out your perfect pair, it’s all about finding the right balance between fit and fabric. Look for a high-rise cut if you love a snatched waist moment, or go mid-rise for a more relaxed vibe. Fabrics with a bit of stretch are your best friend—think soft knits or ponte blends that move with you, not against you. If you’re feeling adventurous, details like the windsor faux fringe pants or windsor fringe pants add just enough edge to keep things interesting, especially if you’re the type who likes a little texture or movement in your look. These styles are also a fun way to break out of a denim rut without sacrificing comfort. And don’t sleep on the gifting potential—flared pants make a thoughtful present for the friend who’s always “borrowing” your clothes, the sister who’s updating her wardrobe, or anyone who appreciates a piece that works for everything from study sessions to spontaneous road trips. For those craving even more comfort and flexibility, check out the full range of Stretch Flare Pants—they’re basically the secret weapon for looking put-together on days when you’d rather be in pajamas.

Styling flare pants is all about embracing that mix of retro-inspired shape with modern, personal twists. Cropped lengths show off your favorite shoes (white sneakers, chunky loafers, or ankle boots—take your pick), while full-length flares can elongate your legs and add a little drama to your stride. Layer them under oversized jackets, pair with tucked-in graphic tees, or add a statement belt for a dose of personality. The beauty of casual flares is how they adapt: they’re just as at home in a lecture hall as they are at brunch, just as ready for a midweek movie night as a Sunday stroll. If you’re after a closet staple that can keep up with your calendar and your ever-changing style mood, flare pants are the answer. They’re not just another trend—they’re a foundation piece you’ll reach for again and again, season after season.

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