Pants For Date Night
Pants for date night? Oh, babe, you already know the answer is yes. Whether you’re serving main character energy at rooftop drinks or plotting a little mischief over candlelit pasta, your outfit should be as bold as your plans. Slip into pants for date night that let you flirt, dance, and steal the spotlight—no questions asked. With every move, you’ll have them wondering how one girl can look this good and keep her cool. Let’s make some memories (and maybe a little trouble), one iconic fit at a time.
$39.90
A chic pair of high-rise black skinny pants in coated faux leather with minimal stretch.
$39.90
A sleek pair of black faux leather pants with a high-rise waist and straight-leg silhouette.
$35.90
A chic black ponte knit trouser with a high-rise waist and flattering wide-leg silhouette.
$28.90
A chic pair of black ponte capri pants with a high-rise waist and side slit accents.
$39.90
A pair of black faux leather high-rise flare pants with a hip-hugging fit and sleek finish.
$49.90
A dark denim high-rise pant featuring a pinstripe pattern and flattering wide-leg silhouette in denim fabric.
$34.90
A pair of black abstract print wide-leg pants crafted from stretchy knit fabric for a flattering fit.
$39.90
A stylish pair of brown faux leather flared pants with a high-rise waist and sleek fit.
$49.90
A pair of black knit flare pants with all-over rhinestone embellishments and a high-rise waist.
$15.97 $36.90 57% off
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 chic leopard print and high-rise waist.
$9.97 $29.90 67% off
A boho chic black sheer lace flare pant with a high-rise waist and hip-hugging fit.
$46.90 - $49.90
A chic olive cargo jogger with high-waist, metal ring trims, and elastic hem for a sporty look.
$42.90
A pair of medium denim high-rise boyfriend jeans with trendy knee slits and multi-button closures.
$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 hem and multiple pockets.
$49.90
A chic brown knit jumpsuit featuring an open back, hoop neckline, and wide-leg silhouette.
$46.90
A pair of high-rise boyfriend jeans in denim with distressed accents and a cuffed hem.
$46.90
A sultry black jumpsuit featuring a cowl halter neckline, cutout back, and wide-leg silhouette.
$14.97 $34.90 57% off
An ivory sheer lace flare pant featuring a high-rise elastic waistband and hip-hugging fit.
$34.90
A trendy wide-leg pant in brown abstract print with a flattering high-rise waist.
$49.90
A sultry black knit jumpsuit featuring a cutout bodice and wide-leg silhouette.
$9.97 $29.90 67% off
A brown high-rise knit flare pant with a fold-over waist and ribbed hacci fabric for comfort.
$34.90
A pair of black tropical print wide-leg pants crafted from stretchy knit fabric for a luxe vacation vibe.
$42.90
A pair of brown satin wide-leg palazzo pants featuring a mid-rise waist and hidden side pockets.
$29.90
A pair of romantic ivory sheer lace flare pants perfect for making a statement at festivals.
$59.90
A pair of black denim jeans featuring a mid-rise waist and dual side lace-up detailing.
$18.97 $44.90 58% off
A pair of gold lurex knit pants featuring a mid-rise drawstring waist and straight-leg fit.
$69.90
A pair of medium denim straight-leg jeans featuring rhinestone-studded star accents and classic five-pocket styling.
$49.90
A pair of dark denim mid-rise jeans featuring flared legs and playful star patch back pockets.
$14.97 $36.90 59% off
A pair of dark denim capri pants featuring a mid-rise waist, front seam detailing, and a form-hugging fit.
Now Trending
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
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
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: M | Knit Fabric
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
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
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
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: S
Windsor Spicing Things Up Mid-Rise Flare Fringe Pants in Black
$24.97 $59.90
58% off
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: 9 | Leather
Printed to perfection in a flattering wide-leg silhouette, these pants boast a classic high-rise waist. Pair with the matching top. Fit & FeaturesAbstract print, stretchy knit fabric, Cowl halter neckline, tie straps, Open back, Fitted crop hem, Runs true to size, Shop The Matching Top: Sultry Effect Abstract Cowl Halter Crop Top Free Shipping on All Orders Over $75. | Windsor Sultry Effect Abstract Wide-Leg Pants in Black | Size: L | Knit Fabric
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: XL
Pants For Date Night
Ready to turn heads and break hearts? Your date night just got a major upgrade, babe. When it comes to picking the perfect pair of pants for that special evening, it’s all about mixing comfort with a little bit of main character energy. Whether you’re headed for rooftop cocktails, a candlelit dinner, or a spontaneous adventure with your favorite partner in crime, the right pants can set the mood for the whole night. Think curve-hugging faux leather that makes you feel unstoppable, wide-leg silhouettes that flirt with every step, or tailored styles that say “I woke up like this” (but, you know, better). It’s about finding that sweet spot where you feel just as fabulous sitting across from your crush as you do strutting down the street after. And let’s not forget those little details—like a flirty slit at the ankle or a daring cutout at the waist—that make your look uniquely yours. The Windsor girl knows that date night is her time to shine, and she’s not afraid to play with bold prints, luxe textures, or a pop of color that says “I’m here for a good time AND a long time.”
Pants for date night are the ultimate power move, and they’re not just for you—they make an epic gift for your fashion-loving BFF, your sister who’s finally saying yes to that cutie from the coffee shop, or even as a treat-yourself moment (because who says you need a plus one to look this good?). These picks are perfect for anyone who wants to feel confident and comfortable, from first dates and long-term loves to spontaneous girls’ nights out. And if you’re feeling a little extra, you can always pair your pants with a killer crop top, a dreamy bodysuit, or a blazer that means business. Plus, if you’re in the mood to switch things up, don’t sleep on the magic of a skirt moment—check out the latest Date Night Skirts for even more ways to slay your next night out. No matter how you style it, your date night look is all about embracing your confidence, living in the moment, and making memories that are as unforgettable as your outfit. So go ahead, step into your power, and let your pants do the talking—because tonight, the spotlight is all yours.