High Waisted Tropical Pants

High waisted tropical pants are your ticket to instant main character energy. Whether you’re plotting your next getaway or just want to bring some vacay vibes to your everyday, these bold bottoms know how to turn every sidewalk into a runway. Slip into playful prints and breezy silhouettes that scream confidence—because you deserve to feel like the fearless, fun-loving icon you are. Let’s get those good vibes going and show the world how high waisted tropical pants were meant to be worn: with attitude, sunshine, and a whole lot of style.

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Windsor Retro Remix Striped Flare Pants in Brown

$39.90

A pair of brown striped knit flare pants featuring a smooth high-rise waist and hip-hugging fit.

Windsor Nine To Five Straight-Leg Crepe Trouser Pants in Black

$34.90

A stylish black crepe trouser with a high-rise waist and straight-leg silhouette for workwear.

Best Seller

Wild Intent Snake Print Pants in Taupe

$59.90

A pair of taupe snake-print faux leather pants with a sleek straight-leg silhouette and glossy finish.

Windsor Cozy Girl Chenille Knit Flare Pants in Brown

$44.90

A pair of brown chenille knit flare pants featuring a high-rise waist and fold-over ribbed waistband.

Chill Time Rib Knit Flare Pants in Brown

$36.90

A pair of brown rib knit flare pants featuring a high-rise foldover waistband and hip-hugging fit.

Lounge Goals Rib Knit Flare Pants in Green

$39.90

A green rib knit pant featuring a high-rise foldover waistband, adjustable side drawstrings, and flared hem.

No Second Guess Faux Leather Straight Leg Pants in Black-2

Best Seller

No Second Guess Faux Leather Straight Leg Pants in Black-2

$44.90

A pair of black faux leather straight leg pants featuring a smooth finish and tailored silhouette.

Windsor Midnight Spark Rhinestone Flare Pants in Black

$69.90

A pair of black stretch flare pants adorned with allover rhinestones and a smooth high-rise waistband.

Now Trending

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

High Waisted Tropical Pants

High waisted tropical pants are the kind of wardrobe hero you reach for when you want to channel vacation vibes—no matter what the calendar says. Think lush, leafy prints and bold botanicals that instantly transport you to somewhere a little sunnier, even if you’re just running errands or meeting friends for brunch. These pants are all about easy confidence: the high-rise fit flatters every curve, smoothing out your silhouette and giving you legs for days, while the relaxed, flowy cut keeps things breezy and unfussy. They’re crafted from fabrics that feel like a gentle breeze—lightweight linen, soft rayon, airy cotton—so you can move, lounge, or dance your way through the day without a second thought. And the styling options? Endless. Tuck in a crisp white tee for that effortless model-off-duty look, or pair with a cropped tank and strappy sandals for a little more drama. Heading somewhere with a chill in the air? Layer up with an oversized denim jacket or a slouchy knit—tropical prints don’t have to hibernate just because the temperature drops. In fact, there’s something unexpectedly chic about mixing a bold, leafy pant with cozy winter textures, like a chunky sweater or a tailored coat.

These pants aren’t just a treat for yourself—they’re also a thoughtful, joyful gift for anyone who could use a little escape in their everyday. Picture gifting a pair to your best friend before her winter getaway, or surprising your sister who’s always on the hunt for something unique and comfortable to wear to work, class, or a casual date night. High waisted tropical pants make dressing feel like play: they’re perfect for spontaneous plans, suitcase packing, or just adding a pop of color to gray December days. They work for all ages and body types, and they’re a favorite among anyone who values comfort as much as style. Plus, the details make all the difference—think pockets deep enough for your phone, adjustable waistbands, and just the right amount of swish with every step. If you’re planning a warm-weather trip or just want to manifest a little more sunshine in your routine, these pants are a no-brainer. For even more options and inspiration, check out our curated selection of High Waist Beach Pants—because your closet deserves a little vacation energy, too.

Whether you’re lounging at home, making a splash on holiday, or just want to stand out at your next gathering, high waisted tropical pants are the secret weapon you didn’t know you needed. They’re the piece you throw on when you want to look pulled together but feel like you’re still in pajamas—no judgment, just pure style. The best part? They’re versatile enough to evolve with your mood and your plans: swap sneakers for wedges, add a statement earring, or cinch the waist with a belt to change up your look in seconds. And with so many prints and silhouettes to choose from—wide leg, palazzo, cropped, or cargo—you can build a whole collection that feels fresh every time you wear them. That’s the beauty of high waisted tropical pants: they’re not just a trend, they’re a mood, a mindset, and a little reminder that style should always feel like a celebration.

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