Vacation Clothing Ideas

Sunshine, sandy toes, and a suitcase full of dreams—it's time to dive into those vacation clothing ideas that are as unforgettable as your next getaway. Whether you're jet-setting to a tropical paradise or planning a chic city escape, every Windsor girl knows the secret to slaying those vacay vibes is all about the right wardrobe. Picture breezy skirts that dance with the ocean breeze, dresses that turn heads faster than a sunset cocktail, and tops that make every moment Instagram-worthy. Your adventure awaits, and with these killer outfit ideas, you'll be living your best life in style. So pack your bags, grab your shades, and let's make some memories!

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$38.90

4.577778 star rating

A white sleeveless ribbed knit midi dress featuring a V-neckline and chic high front slit.

Sale

$19.97 $46.90 57% off

4.75 star rating

A vibrant yellow skater dress with a ruffled skirt, halter tie-back, and smocked high waist.

$44.90

4.6 star rating

A brown cotton-blend romper with a halter plunge neckline and playful skater silhouette.

$39.90

5 star rating

A breezy ivory lace maxi skirt with a high-rise waist, side slit, and asymmetric hem.

$44.90

4.6 star rating

A gold metallic knit maxi dress featuring a plunge cowl halter neckline and adjustable strappy open back.

$42.90

4.6 star rating

An ivory knit wrap skirt with a tie-waist and cascading fringe hem for a chic getaway look.

Sale

$19.97 $59.90 67% off

4 star rating

An ivory A-line maxi dress featuring gauze fabric, sheer lace insets, and a faux leather belt.

Sale

$19.97 $46.90 57% off

4.5 star rating

A chic black knit jumpsuit featuring a strapless neckline and flattering wide-leg silhouette.

$39.90

4.75 star rating

A denim mini skort with a mid-rise adjustable belted waist and form-hugging silhouette.

$39.90

4.5 star rating

A sheer white crochet knit cover-up dress with long sleeves, plunge neckline, and chic hoop insert.

$32.90

4.5 star rating

A natural crochet maxi skirt featuring a high-rise waist and sultry high front slit.

Sale

$19.97 $54.90 64% off

5 star rating

A denim woven maxi dress featuring a flowy ruffled silhouette, square neckline, and spaghetti straps.

$38.90

5 star rating

A vibrant pink mini dress featuring a leopard snake print, mesh fabric, side cutout, and ruffled slit.

Sale

$12.97 $29.90 57% off

5 star rating

An off-white cotton crop top featuring flowy short sleeves, a tie-front, and a flattering V-neckline.

$34.90

4.666667 star rating

A sheer mesh zebra print maxi skirt in brown, perfect for vacation or going out.

Sale

$10.97 $24.90 56% off

4 star rating

An olive tropical crop top with a strappy lace-up back and trendy palm print.

Sale

$14.97 $34.90 57% off

4.5 star rating

A chic brown strapless maxi dress with a high slit and flattering bodycon silhouette.

$44.90

5 star rating

A sultry black floral maxi dress with a V-neckline and form-hugging silhouette, perfect for vacations.

$34.90

3 star rating

A mocha halter jumpsuit featuring a cutout bodice and flattering wide-leg silhouette in stretchy knit.

Sale

$6.97 $19.90 65% off

4.5 star rating

A black tropical print crop top with a plunging V-neckline and ruffled babydoll hem.

Sale

$14.97 $34.90 57% off

5 star rating

A trendy wide-leg pant in brown abstract print with a flattering high-rise waist.

$29.90

3 star rating

A black floral mesh crop top featuring long sleeves, a tie-front closure, and an ultra-cropped hem.

Sale

$20.97 $49.90 58% off

5 star rating

A sultry black knit jumpsuit featuring a cutout bodice and wide-leg silhouette.

$36.90

5 star rating

A natural high-rise mini skort featuring a printed woven overlay, side tie, and stretchy knit shorts lining.

Sale

$10.97 $26.90 59% off

5 star rating

A vibrant orange floral tube top in chiffon with a tie-back detail and stretchy smocked panel.

Sale

$16.97 $39.90 57% off

5 star rating

A black floral mesh maxi skirt featuring a high-rise waist, dramatic front slit, and attached panty lining.

Sale

$12.97 $29.90 57% off

A black tropical print crop top in stretchy knit fabric with long sleeves and a sultry tie-front.

$14.90

2 star rating

A beige jelly sandal featuring a thong strap, pretty flower accent, and easy open-back design.

Sale

$10.97 $24.90 56% off

A black tropical print maxi skirt in sheer mesh with a high-rise waist and sultry side slit.

Sale

$16.97 $39.90 57% off

A black tropical print maxi skirt in stretchy knit fabric featuring a high front slit and flowy silhouette.

Sale

$18.97 $44.90 58% off

A brown tropical-print knit jumpsuit featuring a halter neckline, cutout bodice, and wide-leg silhouette.

$36.90

A pair of mid-rise denim hot shorts with a color wash tint and cheeky fit.

$34.90

An ivory crochet lace kimono with a relaxed fit, perfect for festival or vacation vibes.

$32.90

A relaxed off-white linen-blend crop top featuring a collared neckline and button-down front.

Sale

$9.97 $29.90 67% off

A boho chic ivory lace flare pant with a high-rise waist and sheer floral design.

Sale

$9.97 $56.90 82% off

A floral chiffon romper in natural with a strapless neckline and flattering drop waist seam.

$44.90

4.954546 star rating

A red floral print mesh maxi dress with a sleeveless sweetheart neckline and lace trim.

$35.90

5 star rating

A pink sleeveless bodycon midi dress with a square neckline and stretchy knit fabric.

$39.90

4.7 star rating

A brown knit midi dress with long sleeves, off-the-shoulder neckline, and ruched bodycon fit.

Sale

$19.97 $48.90 59% off

4.5 star rating

A flirty white mini skater dress featuring a breezy eyelet knit and charming tie-back detail.

Sale

$10.97 $26.90 59% off

4.857143 star rating

A rust satin paisley scarf top with a strapless neckline and tie-back design for effortless style.

$24.90

4.714286 star rating

A form-hugging ivory crop tube top with a strapless neckline in stretchy knit fabric.

Sale

$17.97 $42.90 58% off

4.75 star rating

An ivory halter romper with ruffled drop waist, faux leather belt, and hidden fitted shorts.

$39.90

4.75 star rating

A strapless black and white striped mini dress with a cutout bodice and bodycon silhouette.

$44.90

5 star rating

A sleeveless brown denim mini dress with a V-neck collar and zip-up front closure.

$26.90

4.666667 star rating

A chic ivory lace mini skirt with a high-rise waist and form-hugging fit.

$39.90

3.666667 star rating

A khaki denim skort with a high-rise waist and ruched drawstring for a unique touch.

Sale

$14.97 $44.90 67% off

4.5 star rating

A taupe paisley skater dress with a halter V-neck and stretchy smocked bodice.

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Wild At Heart Long Fringe Skirt in Tan
(33) 4.848485 star rating

Channel your western side with this trendy-chic skirt that will level up your festival look! It features a high-rise waist, an asymmetric mini-length hem with a form-hugging fit, and long fringe detailing that cascades to your ankles. The stylish fringe design will dance with you to your favorite band! Complete your 'fit with a cropped graphic tee and cowboy boots. Fit & FeaturesHigh-rise waist, Back zipper, hook and eye closure, Asymmetric mini-length hem, Form-hugging fit, Long fringe design, ankle-length hem, Faux suede fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Wild At Heart Long Fringe Skirt in Tan | Size: XS | Faux Suede

Bold Staple Ruched Asymmetrical Midi Skirt in Black
(10) 5 star rating

Fit & FeaturesStretchy smooth knit-lined fabrication, High-rise fit, Ruching, Asymmetrical high-side slit, Midi length hem, Runs true to size, Shop Matching Crop Top: Bold Staple Long Sleeve Crop Top Free Shipping on All Orders Over $75. | Windsor Bold Staple Ruched Asymmetrical Midi Skirt in Black | Size: XS

Windsor Sleek Status Faux Leather Mini Skirt in Black
(6) 3.6666667 star rating

Level up your sleek status with this chic mini skirt made with smooth faux leather fabric to elevate your casual 'fits. It features a high-rise waist, a side slit accent at the hem, and a form-hugging silhouette to highlight your stunning curves. Fit & FeaturesFaux leather fabric, plenty of stretch, High-rise elasticized waist, Side slit, Mini-length hem, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Status Faux Leather Mini Skirt in Black | Size: S

Keep A Secret Lace Slit Maxi Skirt in Black
(6) 4.8333335 star rating

Make a statement in this lace slit maxi skirt. With sheer lace, ruching, and a high slit, it's your go-to for that effortlessly chic vibe. Fit & FeaturesSheer lace fabric with mini-length knit lining, plenty of stretch, High-rise waist, Ruching, High front slit, Maxi-length hem, Flowy silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Keep A Secret Lace Slit Maxi Skirt in Black | Size: M | Lace Fabric/Knit Fabric/Sheer Lace Fabric

Breezy Boho Sheer Lace Asymmetric Maxi Skirt in Ivory
(5) 5 star rating

Channel an effortless boho vibe in this breezy sheer lace maxi skirt featuring a high-rise waist, ruched detailing with an adjustable drawstring, a high-cut side slit, and an asymmetric hem with a flowy silhouette. Perfect for pairing with a crop top and booties. Fit & FeaturesSheer lace fabric with mini-length knit lining, plenty of stretch, High-rise waist, Ruching, adjustable drawstring, High side slit, Asymmetric maxi-length hem, Flowy fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Breezy Boho Sheer Lace Asymmetric Maxi Skirt in Ivory | Size: L | Lace Fabric/Knit Fabric/Sheer Lace Fabric

Windsor Iconic Getaway Tie-Waist Wrap Fringe Skirt in Ivory
(5) 4.6 star rating

Get ready for an iconic getaway with this tie-waist wrap fringe skirt perfect for days spent under the sun or sipping on drinks poolside! Fit & FeaturesCrochet knit design, sewn-in knit lining, Wrap-tie waist, Back zipper and hook-eye closure, Cascading fringe hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Iconic Getaway Tie-Waist Wrap Fringe Skirt in Ivory | Size: S | Knit Fabric

Call Me Cutie Floral Eyelet Mini Skirt in White
Sale
(4) 4.5 star rating

Get ready for everyone to call you cute in this floral mini skirt designed with a flirty layered ruffle that captures attention and a mini-length hem that lets you flaunt your figure. Pair with the matching top. Shop Matching Top: Call Me Cutie Lace-Up Floral Eyelet Corset TopFit & FeaturesFloral print, eyelet woven lined fabric, Stretchy smocked high-rise waist, Layered ruffle , Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Call Me Cutie Floral Eyelet Mini Skirt in White | Size: L

Windsor Vacay Ready High Rise Crochet Maxi Skirt in Natural
(4) 4.5 star rating

Heading on vacation? Don't forget to grab this vacay ready high-rise crochet maxi skirt with a sultry high front slit that flaunts some leg. Pair with the matching top and your fave shades! Fit & FeaturesCrochet fabric, stretchy knit lining, High-rise elasticized waist, High front slit, Flowy maxi-length silhouette, Runs true to size , Shop The Matching Top: Vacay Ready Tie-Front Bandea Crochet Crop Top Free Shipping on All Orders Over $75. | Windsor Vacay Ready High Rise Crochet Maxi Skirt in Natural | Size: L | Knit Fabric

Windsor Floral Sensation High Rise Maxi Skirt in Pink
Sale
(4) 5 star rating

Everyone will adore your look in this floral mesh maxi skirt perfect for vacay or weekend plans! With a high-rise waist, it accentuates your figure while the bodycon fit flatters your curves, and the center back slit offers movement. Complete the look with the matching top. Shop The Matching Top: Floral Sensation Strapless Crop BustierFit & FeaturesFloral print, mesh fabric lined with stretchy knit, High-rise waist, Bodycon fit, Center back slit, Maxi-length, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Floral Sensation High Rise Maxi Skirt in Pink | Size: S | Mesh Fabric/Mesh Fabric

Boho Babe Lace Hanky Hem Maxi Skirt in Ivory
Sale
(4) 4.75 star rating

Live out your boho era in this airy sheer lace maxi skirt with a mini-length lining for a chic look. The long flowy silhouette will create that effortlessly cool vibe. Fit & FeaturesSheer lace fabric with mini-length knit lining, High-rise waist, Hip-hugging fit, Maxi-length hanky hem, Flowy silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Boho Babe Lace Hanky Hem Maxi Skirt in Ivory | Size: L | Lace Fabric/Knit Fabric/Sheer Lace Fabric

Vacation Clothing Ideas