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Trendy Pants That Serve Every Summer Mood

Step into the season with trendy pants designed to fit your every vibe—whether you’re catching golden hour with the group chat or slaying solo on the 'gram. Windsor’s latest pants drop is all about bold energy, soft textures, and silhouettes that stun from brunch dates to beach escapes. Think flare pants with a vintage kick, black pants that do double duty for work and play, and wide-leg styles that bring the drama—without you breaking a sweat.

Serving options? Absolutely. From high-rise cargo pants and ankle-length joggers to polished trouser fits and beachy jumpsuits in tropical prints, your summer wardrobe starts here. Play it cool in crochet pants, elevate your edge with faux leather pants, or keep things casual in our soft-knit leggings and skinny styles that contour and move with you. And don’t sleep on our matching pant sets and new prints—they’re made for mixin’, matchin’, and maximum impact.

We’re talking pant perfection that pairs effortlessly with corset tops, trendy bodysuits, and that blazer you’ve been waiting to style. Need outfit ideas? A flared silhouette plus strappy heels is your throwback moment. A classic black pant with a pop-color top? That’s your main character energy.

Not sure where to start? Get the vibe check from our fave styling how-tos:

Whether you're planning a weekend fit or a wow-worthy workday look, Windsor’s trendy pants collection delivers bold prints, luxe fabrics, and must-have styles for your every summer moment. Shop online, in-app, or IRL at a Windsor store near you.

  • Movin' On Up High-Rise Parachute Cargo Pants

    Elevate your sporty girl style in these parachute cargo pants for casual slays! The pants feature a high-rise drawstring waist with side pockets, one back pocket, a wide-leg silhouette, large side pockets with velcro closures, pleating along the hem, and adjustable drawstring cuffs so you customize the style. Complete the look in a sleek corset top for a day or evening out!

    Fit & Features

    • High-rise drawstring waist, side pockets, one back pocket
    • Front hidden button and zipper closure
    • Wide-leg silhouette
    • Large side pockets, velcro closures
    • Pleating at the hem, adjustable drawstring cuffs
    • Smooth woven non-stretch fabric
    • Runs true to size

    Style Number/Barcode: 06302-0782

    Category Name: Pants

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fashion Boot Camp Denim Cargo Joggers

    Step up as a stylish cadet in these denim cargo joggers! The pants feature a flattering high-rise waist, side pockets, and lower cargo flap pockets with dual button closures, a jogger-style leg, and a pull strap along the cuff. Complete the look with the matching jacket for casual hangs or school! 

    Shop Matching Jacket: Fashion Boot Camp Denim Bomber Jacket

    Fit & Features

    • High-rise waist
    • Front button and hidden zipper closure, belt loop accents
    • Side pockets, lower cargo flap pockets, dual button closures
    • Jogger-style leg
    • Pull tab straps along the cuff
    • Denim woven fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06302-0780

    Category Name: Pants

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Iconic Vibes Pinstripe Trouser Pants

    Create an iconic look and have a major it-girl moment in these pinstripe trouser pants! They feature a high-rise waist, dual front pockets, dual faux back pockets, a wide-leg silhouette, and a relaxed fit. The woven fabric features a pinstripe pattern for a chic flair. Complete your look with the matching vest or blazer to wear from the office to dinner!

    Shop Matching Tops: Iconic Vibes Pinstripe Cropped Vest, Iconic Vibes Pinstripe Blazer

    Fit & Features

    • High-rise waist, back elastic waistband, pleating
    • Hidden front zipper, hook and bar closure
    • Dual front pockets, dual faux back pocket slits
    • Wide-leg silhouette, relaxed fit
    • Pinstripe pattern
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06402-1334

    Category Name: Pants

    Price: $3.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Play Date High Rise Straight-Leg Pants

    Play up a cute and comfy style with these knit pants for all of your casual plans! The pants feature a flattering high-rise banded waist and a straight-leg silhouette on stretchy rib knit fabric. Complete the look with the matching cardigan.

    Shop Matching Top: Play Date Sweater Knit Cardigan

    Fit & Features

    • High-rise banded waist
    • Straight leg silhouette
    • Stretchy sweater rib knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06502-2391

    Category Name: Pants

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Always Ahead High-Rise Flare Pants

    You'll always be ahead of the trends in these flare pants perfect for elevating your everyday look! The pants feature a flattering high-rise waist, hip-hugging fit, and flared hem on stretchy rib knit fabric. Style with the matching top.

    Shop Matching Top: Always Ahead One-Shoulder Tunic Top

    Fit & Features

    • High-rise elastic banded waist
    • Hip-hugging fit
    • Flared hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 06502-2398

    Category Name: Pants

    Price: $5.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trish Mid-Rise Carpenter Wide-Leg Denim Jeans

    Casual coolness is what the Trish mid-rise denim jeans are all about! They feature a flattering mid-rise waist, wide-leg silhouette, and carpenter-style strap and pocket detailing on vintage-inspired denim fabric with a slight stretch. Complete the look in a cute crop top and mules for brunch or a girl's day!

    Fit & Features

    • Mid-rise waist
    • Wide-leg silhouette
    • Carpenter-style strap, back pocket detail
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Denim fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06602-0459

    Category Name: Pants

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Autumn Chill Crochet Wide-Leg Pants

    You'll love styling these crochet knit pants on chill autumn days! They feature a flattering high-rise elasticized waistband, a wide-leg silhouette, and ribbed cuffs. Complete the look in a basic top, cozy jacket, and slippers! 

    Fit & Features

    • High-rise elasticized waistband
    • Wide-leg silhouette
    • Ribbed cuffs
    • Crochet knit fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06502-2392

    Category Name: Pants

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Playing For Keeps Cargo Straight Leg Denim Jeans

    You'll want to keep these cargo denim jeans on rotation! The jeans feature a flattering mid-rise waist with an adjustable belt, a straight-leg silhouette, and six cargo-style flap pockets on premium denim fabric with slight stretch. Complete the look in a sassy corset top for a bar crawl with friends!

    Fit & Features

    • Mid-rise waist
    • Adjustable belt, buckle closure
    • Straight-leg silhouette
    • Six cargo flap pockets
    • Front button and hidden zipper closure, belt loops
    • Premium denim fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06302-0771

    Category Name: Pants

    Price: $6.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Big On Comfort High-Rise Cargo Joggers

    These high-rise cargo joggers will have you looking like a fashionista no matter where you go! The pants feature a slim silhouette, pleated striped panels, side pockets, and cargo-style pockets, and elasticized cuffs, you'll be stylishly equipped to take on the world. Plus, they're crafted from a brushed twill woven fabric, so you'll be comfy and cozy like a boss! Style the joggers with a crop top for daytime plans!

    Fit & Features

    • High-rise waist
    • Slim silhouette, jogger-leg
    • Pleated striped panels, elasticized cuffs
    • Front button, hidden zipper closure, belt loop accents
    • Side pockets, cargo-flap pockets, faux back pockets
    • Brushed twill woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0788

    Category Name: Pants

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Look Again Ponte High-Rise Cargo Joggers

    Reinvent your wardrobe with these ponte joggers perfect for everyday styling! The jogger pants feature a modern, high-rise waist, and a slim relaxed leg silhouette for an ultra-flattering fit. Plus, all the functional details you need—side and back pockets, cargo-style flap pockets, elasticized cuffs, and pintuck seams down the front for added flare. Complete the look in a basic long sleeve top and pumps for a casual business lunch or meeting up with the girls!

    Fit & Features

    • High-rise waist, belt loop accents
    • Hidden front hook-eye and zipper closure
    • Side and back pockets, cargo-flap pockets
    • Pintuck seams down the front
    • Slim, relaxed fit silhouette, elasticized cuffs
    • Smooth ponte knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06502-2402

    Category Name: Pants

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Play Fair High-Rise Camouflage Cargo Pants

    These camouflage pants play fair everywhere you wear them! Featuring a high-rise waist, a flattering wide-leg silhouette, cargo-style flap pockets, and a trendy camouflage print on woven fabric. Style the cargo pants with a basic bodysuit top and mules for a day out!

    Fit & Features

    • High-rise waist
    • Wide-leg silhouette
    • Front button, hidden zipper closure, belt loop accents
    • Side pockets, lower cargo-style flap pockets
    • Back faux flap pockets
    • Camouflage print, woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0786

    Category Name: Pants

    Price: $6.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • High-Rise Wide-Leg Carpenter Pants

    These wide-leg carpenter pants will get you that trendy street style you've been seeing all over your feed. They feature a high-rise waist, two large front pockets, two back pockets, a utility-style side strap, a wide-leg silhouette, and an overall relaxed fit. The lightweight cotton-blend woven fabric has a minimal stretch for comfortable wear. Pair these carpenter pants with a graphic tee and sneakers for a casual-cool everyday look.

    Fit & Features

    • High-rise waist
    • Two large front pockets
    • Two back pockets
    • Single utility-style side strap
    • Wide-leg silhouette, relaxed fit
    • Cotton-blend woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06302-0794

    Category Name: Pants

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Mood Hacci Knit Wide-leg Pants

    These super comfy hacci knit wide-leg pants will have you in a totally relaxing weekend mood! They feature a high-rise elasticized drawstring waist, a tie-front design, and a wide-leg silhouette. The ultra-soft hacci knit fabric has plenty of stretch. Pair these pants with a basic cropped tank for a cute and casual loungewear look.

    Fit & Features

    • High-rise elasticized drawstring waist
    • Tie-front design
    • Wide-leg silhouette
    • Soft hacci knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06502-2394

    Category Name: Pants

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Favorite Trend High-Rise Oversized Sweatpants

    These comfy high-rise oversized sweatpants will be your new favorite trend to style! They feature a high-rise waist with an elastic waistband for comfortable wear, dual side pockets, a relaxed wide-leg silhouette, and an oversized fit. The heather knit fabric offers plenty of stretch and a soft fleece lining. Pair these sweatpants with a basic crop top and sneakers to look cute as you run errands, or a tube top and mules for a casual-chic 'fit to grab drinks!

    Fit & Features

    • High-rise elasticized waistband
    • Side pockets
    • Wide-leg silhouette
    • Heather knit fabric, soft fleece lining
    • Plenty of stretch
    • Oversized fit

    Style Number/Barcode: 06502-2395

    Category Name: Pants

    Price: $22.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Especially Cool High-Rise Belted Cargo Denim Jeans

    Your street style will look especially cool in these on-trend cargo denim jeans for your off-duty days! They feature a flattering high-rise belted waist with belt loop accents, five flap pockets, and a straight-leg silhouette on rigid denim fabric. Complete the look in a strapless corset for an afternoon lunch and movie!

    Fit & Features

    • High-rise waist, adjustable belt, buckle closure
    • Straight-leg silhouette
    • Five flap pockets, belt loop accents
    • Hidden front zipper and button closure
    • Rigid denim fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06602-0448

    Category Name: Pants

    Price: $6.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Work It High Rise Pinestripe Trouser Pants

    Work it down the hallway in these pinstripe trouser pants to show everyone who's the fashion boss of the office! They feature a flattering high-rise waist, hidden side pockets for keeping your hands warm or cell phone, and a wide-leg silhouette. The pinstripe knit fabric has plenty of stretch. Complete the look in a basic tee, heels, and a chic blazer.

    Fit & Features

    • High-rise waist, belt loops
    • Hidden side pockets
    • Wide-leg silhouette
    • Front button closure, hidden zipper closure
    • Pinstripe print, knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06502-2393

    Category Name: Pants

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Buckle Up High Rise Cutout Flare Denim Jeans

    Get ready for these edgy denim jeans to enter your closet! They feature a Y2K-inspired design with a flattering high-rise waist, side cutouts with adjustable straps and buckle closures, a hip-hugging fit, and a flared hem on premium denim fabric. Complete the look with a cute crop tee for a concert or movie with friends!

    Fit & Features

    • High-rise waist
    • Side cutouts, adjustable straps, buckle closures
    • Back zipper and hook-eye closure
    • Hip-hugging fit
    • Flared hem
    • Premium denim fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06602-0450

    Category Name: Pants

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flare For Glam Mid Rise Rhinestone Pants

    If you've got a flare for glam, these knit pants are perfect for giving your outfits a unique touch! They feature a flattering mid-rise waist, a hip-hugging fit, a flared hem, and an all-over rhinestone-embellished striped pattern on the stretchy knit fabric. Complete the look in a sultry satin bustier for your next night out!

    Fit & Features

    • Mid-rise waist, elastic waistband
    • Hip-hugging fit
    • Flared hem
    • All-over rhinestone embellished striped pattern
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06502-2404

    Category Name: Pants

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cinch It Together Crepe Corset Trouser Pants

    Cinch your workwear style together in these crepe trouser pants essential for looking sharp and chic! They feature a flattering ultra high-rise corset waist with flexible boning inserts, a back zipper closure, a slim hip-hugging fit, and a straight-leg silhouette. Complete the look in a sleeveless top for in the office!

    Fit & Features

    • Ultra high-rise corset waist, flexible boning
    • Back zipper closure
    • Slim hip-hugging fit
    • Straight-leg silhouette
    • Lined crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06502-2354

    Category Name: Pants

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • City Sleek Satin Cargo Joggers

    Look sleek in the city wearing these satin cargo joggers to elevate your style! They feature a flattering high-rise waist, hidden side pockets, a relaxed fit, cargo flap pockets with pull tabs, and an elasticized drawstring cuff. Complete the look in a long sleeve crop top for grabbing cocktails and appetizers!

    Fit & Features

    • High-rise waist, back elasticized band
    • Hidden side pockets, cargo flap pockets, pull tabs
    • Relaxed fit
    • Elasticized drawstring cuff
    • Front button and hidden zipper closure, belt loop accents
    • Smooth satin fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06402-1360

    Category Name: Pants

    Price: $20.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Serious Chills Velour Cargo Joggers

    Sit back and chill or go on a coffee run in these trendy velour joggers! It features a flattering mid-rise elasticized waist with hidden side pockets for keeping your hands warm, a relaxed fit, cargo flap pockets, and elasticized cuffs. The ultra-soft velour fabric has a moderate stretch. Complete the look with the matching jacket and your favorite sneakers!

    Shop Matching Jacket: Serious Chills Velour Zip Up Hoodie Jacket

    Fit & Features

    • Mid-rise elasticized waist
    • Hidden side hip pockets
    • Cargo flap pockets, velcro closures
    • Relaxed fit
    • Elasticized cuffs
    • Soft velour fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06502-0973

    Category Name: Pants

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fashion Doll Rhinestone Faux Leather Flare Pants

    Live your best dream life as an iconic fashion doll this Halloween! These sleek faux leather flare pants feature a high-rise waist, a lattice front design with a tie closure, a hidden side zipper closure, a hip-hugging fit, a form-hugging fit throughout the leg, and a flared hem. The lined faux leather fabric features mini rhinestone embellishments down the front of the leg for that stylish and stunning sparkle. Complete your fab costume with the matching corset top and rhinestone boots!

    Shop Matching Top: Fashion Doll Rhinestone Faux Leather Corset Top

    Fit & Features

    • High-rise waist, hidden side zipper, hook and eye closure
    • Lattice front design, tie closure
    • Hip-hugging fit, form-hugging fit throughout the leg
    • Flared hem
    • Rhinestone embellishments down the leg
    • Faux leather fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06402-1331

    Category Name: Pants

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Utilitarian Flare Faux Leather Cargo Joggers

    Step up your edgy style in these faux leather joggers perfect for concerts or hitting up the bar! They feature a flattering high-rise waist with a partial elasticized band, hidden side pockets, a skinny jogger-style leg silhouette, faux cargo flap pockets, and an elasticized hem. Complete the look in a corset top and rhinestone heels for a hint of sparkle!

    Fit & Features

    • High-rise waist, partially elasticized band
    • Front button and hidden zipper closure
    • Hidden side pockets, faux cargo flap pockets
    • Skinny-leg jogger silhouette
    • Elasticized hem
    • Lined faux leather fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06402-1358

    Category Name: Pants

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stroll The City Mid Rise Lace-Up Flare Pants

    Stroll the city sidewalks in these fab and fierce flare pants to elevate your style! They feature a flattering mid-rise waist, eye-catching side lace-up designs, a hip-hugging fit, and a flared hem on smooth knit fabric with minimal stretch. Complete the look in a trendy graphic tank top for dinner and drinks!

    Fit & Features

    • Mid-rise waist
    • Back zipper and hook-eye closure
    • Side lace-up designs
    • Hip-hugging fit
    • Flared hem
    • Smooth knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06602-0445

    Category Name: Pants

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance