Vacation Pants

Vacation pants are your ultimate ticket to carefree style and endless adventures! Whether you're jetting off to a tropical paradise or exploring a bustling city, these pants are all about bringing the heat with comfort and flair. Think breezy fabrics, vibrant patterns, and fits that let you move like the world is your runway. Perfect for those spontaneous dance-offs or sunset strolls on the beach, vacation pants are your go-to for turning heads and making memories. So pack your bags, grab your favorite pair, and get ready to slay every getaway with confidence and sass!

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Windsor Major Cutie Cargo Joggers Pant in Black

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Windsor Major Cutie Cargo Joggers Pant in Black

$46.90

A chic black cargo jogger with high-rise waist, metal ring trims, and elastic cuffed hems.

Windsor 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.

Out For The Day High-Rise Cargo Pants in Brown

$42.90

A stylish pair of brown high-rise cargo pants with adjustable drawcord hems and multiple pockets.

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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

Vacation Pants

Vacation pants are the unsung heroes of any getaway wardrobe—the kind of piece you reach for first when your suitcase is wide open and your itinerary is still a little fuzzy. Whether you’re plotting a mid-winter escape to somewhere sun-soaked or simply dreaming of balmy afternoons and breezy evenings, the right pair of vacation pants can do more than just keep you comfortable—they set the tone for the entire trip. Think fabrics that feel like a soft sigh against your skin: airy linens that let the breeze do its thing, featherweight cottons that move with you from city strolls to sandy boardwalks, and blends that stretch just enough to handle whatever the day brings. It’s not just about staying cool in the heat (though that’s a must), it’s about feeling effortlessly put-together even when you’re living out of a suitcase. Look for details like wide legs that catch the wind, cropped hems that show off your favorite sandals, and drawstrings or elastic waists that keep things flexible after a spontaneous gelato stop. And if your plans include a little adventure—think paddle boarding, hiking, or chasing waterfalls—quick-drying, moisture-wicking fabrics are your best friend, making it easy to transition from wet to dry without missing a beat.

Choosing vacation pants isn’t just about function, though—it’s about finding that perfect blend of comfort and style that makes you feel like the best version of yourself, no matter where you land. Maybe you’re shopping for yourself, prepping for a girls’ trip, or hunting for a gift that says “I support your wanderlust.” Vacation pants are that rare find that works for everyone: the friend who’s always cold on the plane, the sibling who loves a bold print, or the partner who needs something easy to dress up or down. They’re versatile enough to pair with everything from a swimsuit and slides to a crisp button-down for dinner al fresco, and they pack down small, leaving plenty of room in your bag for souvenirs (and maybe one more pair, just in case). The best part? They’re made for repeating—nobody’s judging if you wear the same pair three days in a row because they just work with every vibe. If you’re building a capsule wardrobe for travel, vacation pants are a no-brainer foundation, and they play well with all your favorite tops. For even more mix-and-match magic, check out our curated collection of Vacation Tops—because the only thing better than an outfit that feels effortless is one that looks it, too.

When it comes to packing for a getaway in January, vacation pants are a breath of fresh air—literally. As the temps dip at home, slipping into something light and relaxed is a reminder that adventure (and a little bit of sunshine) is always within reach. Imagine yourself lounging by the pool in a pair of flowy palazzos, exploring a bustling market in cropped cargos, or catching a sunset in wide-leg linens that sway with every step. These pants aren’t just for the beach—they’re for the flight, the brunch, the spontaneous detour to that hidden cove you spotted on Instagram. They’re the piece you’ll thank yourself for bringing, again and again, whether you’re hopping continents or just escaping for a long weekend. And when the trip is over? They slip right into your everyday wardrobe, carrying a little bit of that vacation feeling with you wherever you go.

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