Vacation Looks

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STYLE SPOTLIGHT

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Vacation Dresses & Outfits for Effortless Getaways

Pack light and look luxe in vacay dresses and vacation outfits designed for sun-soaked escapes. Whether you’re poolside at a beach resort or exploring cobblestone streets, Windsor’s resortwear blends breezy fabrics, relaxed silhouettes, and bold prints for travel outfits you’ll want to wear on repeat.

Easy, Packable Styles

Slip into breezy maxi dresses in tropical prints or neutral tones—white, ivory, and tan—for instant cruisewear elegance. Chic rompers and vacay outfits like matching top-and-bottom sets in airy cotton or linen make packing a breeze and styling stress-free.

Day-to-Night Versatility

Transition from sunrise yoga to sunset cocktails in flowy sundresses or relaxed separates. Mix and match colorful vacation-ready separates—think high-waist shorts with off-shoulder tops—or choose effortless travel outfits in knit jumpsuits and wrap skirts that go anywhere.

Resort & Beach Essentials

Complete your look with stylish bikinis under sheer cover-up dresses or mesh tunics. Add slide sandals, statement sunglasses, and a woven tote for poolside chic. From beach days to rooftop lounges, these vacay dresses keep you feeling confident and carefree.

Ready to jet off in style? Explore Windsor’s full collection of vacation dresses and outfits online, in-app, or at your nearest Windsor store.

  • Feeling Fun Cuffed Denim Mini Skirt

    Forever classic with a fun touch, this denim mini skirt boasts a flattering bodycon fit and a unique cuffed hem. Pair with a cute top for a farmer's market!

    Fit & Features

    • Denim fabric
    • High-rise waist, belt loops
    • Front button and hidden zipper closure
    • Dual front and back pockets
    • Mini-length cuffed hem
    • Fitted silhouette
    • Runs true to size

    Style Number/Barcode: 06601-000002

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: LIGHT, DENIM

    Available Size: S

    Product Badge:
    • Sale
  • Glittery Vibes High Slit Maxi Skirt

    Bring on the glittery vibes for your next girl's night in this high slit maxi skirt! Designed with a glitzy glitter knit fabric that has a mini-length lining, this long skirt is glam perfection. It features a high waist, a hip-hugging fit to flaunt your figure, a maxi-length hem with a high-cut back slit for an alluring detail, and an overall form-fitting silhouette for a sultry slay. Complete your going-out look with the matching crop top and clear heels!

    Shop Matching Top: Glittery Vibes Ruched Spaghetti Strap Crop Top

    Fit & Features

    • Textured glitter knit fabric with mini-length knit lining
    • Plenty of stretch
    • High waist
    • Maxi-length hem
    • Back slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-0932

    Category Name: Vacation Looks

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In My Sweet Era Cowl Neck Eyelet Lace Romper

    Enter your sweet era with this eyelet lace romper for the ultimate romantic aura at brunch, birthdays, or showers! The flowy and breezy sleeveless rompers feature a flattering cowl neckline with spaghetti straps and an adorable fit and flare silhouette for all-day twirls. Complete the look in wedges.

    Fit & Features

    • Eyelet lace knit fabric, shorts lining, moderate stretch
    • Spaghetti straps, cowl neckline
    • Fit and flare silhouette
    • Runs true to size

    Style Number/Barcode: 06503-1128

    Category Name: Vacation Looks

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Case In Point High-Rise Trouser Shorts

    Make a polished point in these high-rise trouser shorts with convenient side pockets and a slim-fit silhouette, they're perfect for elevating any OOTD!

    Fit & Features

    • Woven fabric
    • High-rise waist
    • Hidden front hook-eye and zipper closure
    • Side pockets
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 06403-1113

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: In Stock

    Available Color: PINK

    Available Size: L

    Product Badge:
    • Sale
  • Breezy Mood Collared Linen Crop Top

    This breezy linen crop top is a sunny day staple! Designed with a lightweight linen-blend fabric, this top is perfect for your summer weekend plans. It features a collared V-neckline with a partial button-down front, a single chest pocket, cap sleeves, a twist-front cropped hem, and a relaxed fit. Style with wide-leg pants and sandals.

    Fit & Features

    • Linen-blend fabric
    • Collared V-neckline
    • Chest pocket, button-down front
    • Cap sleeves
    • Side zipper closure
    • Twist-front cropped hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06003-2431

    Category Name: Vacation Looks

    Price: $30.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Glam Large Hollow Hoop Earrings

    You'll love the sleek glamour these large brass hollow hoop earrings add to your everyday looks. Perfect for the girlies with sensitive skin, these hoops are hypoallergenic.

    Fit & Features

    • Genuine brass
    • Hollow hoop
    • Hypoallergenic
    • Large hoop design
    • Omega closure

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-000074

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Darling Twirl Crepe Ruffle Skater Dress

    Delight with your darling twirls in this crepe skater dress perfect for family parties or brunch! It features adorable puff short sleeves, a V-neckline, and a ruffled layered short-length hem with a fit-and-flare silhouette. Complete the look in this skater dress with sleek hoop earrings.

    Fit & Features

    • Puff short sleeves
    • V-neckline
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Ruffled layered short-length hem
    • Crepe fabric, partial stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5064

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Instant Staple Double-Slit Mini Skort

    This chic double-slit mini skort will be an instant staple you'll love to style up. It features a high-rise elasticized waist, fitted shorts, and a mini-length front overlay with a double-slit design. The ponte knit fabric offers a moderate stretch. Complete the look with a form-hugging bodysuit and strappy mules.

    Fit & Features

    • High-rise elasticized waist
    • Fitted shorts
    • Mini-length front overlay, double-slit design
    • Ponte knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06503-1074

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Color Me Pretty Satin Abstract Crop Top

    Color you pretty in this satin crop top to brighten up this new season! It features a sleeveless plunge halter neckline, a center hardware insert, and an ultra-cropped hem on smooth satin with an abstract print. Complete the look with the matching bottoms for a vacation!

    Shop Matching Bottoms: Color Me Pretty Satin Abstract Wide-Leg Pants

    Fit & Features

    • Sleeveless plunge halter neckline
    • Front hardware insert
    • Ultra-cropped hem
    • Abstract print
    • Smooth satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-2286

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Totally Heart Flat Sandals

    Fall in love with these heart sandals perfect for everyday styling!

    Fit & Features

    • Almond toe
    • Wide band with heart
    • Flat faux leather insole
    • Trim accents
    • Runs true to size

    Style Number/Barcode: 07405-0227

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: 6.5

    Product Badge:
    • Sale
  • Boho Sleek Cross Concho Chain Belt

    Sleek and trendy, this cross concho chain belt radiates boho-chic vibes. Style over a lace skirt with knee-high boots.

    Fit & Features

    • Cross and concho textured metal design
    • Center stone embellishments
    • Back adjustable chain, lobster clasp closure

    Style Number/Barcode: 07301-000045

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Time For Vacay Tie Front Tropical Crop Top

    This tropical tie front crop top is ready for your next vacay! Features fluttery short sleeves and a tie front cropped hem for a flattering fit. The palm print on lined knit fabric adds a touch of paradise to any outfit. Complete the look with the matching pants.

    Shop Matching Bottoms: Time For Vacay High Rise Tropical Palazzo Pants

    Fit & Features

    • Palm print, lined stretchy knit fabric
    • High rise waist
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06202-0458

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK/WHITE

    Available Size: S

    Product Badge:
    • Sale
  • Sweet But Savage Lace Floral Leopard Mini Dress

    Giving major heartbreaker energy! This flirty A-line mini dress hugs you just right with its mesh fabric and mixed prints. Pair it with heels or a chunky boot—your vibe, your rules.

    Fit & Features

    • Floral leopard print, mesh fabric, stretchy knit lining
    • Sweetheart neckline, adjustable spaghetti straps
    • Lace underwire bust with bow
    • Back zipper and hook-eye closure
    • Princess seams down the front
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000267

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

  • Daydream Tie-Dye Bodycon Mini Dress

    You'll be lookin' like a daydream in this trendy tie-dye bodycon mini dress! Designed with an asymmetric tie-dye pattern on the airy mesh fabric, it features a sleeveless square neckline, bungee spaghetti straps, ruching down the side seams, a mini-length hem, and a bodycon silhouette to accentuate your curves. The sheer mesh fabric includes a full-length knit lining. Style this short dress with platform heels.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Ruched side seams
    • Mini-length hem, bodycon fit
    • Asymmetric tie-dye pattern
    • Sheer mesh fabric, full-length sewn-in knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5481

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Deets Cap Sleeve Open Twist Back Midi Dress

    This crew neck midi dress may look basic from the front but the open back reveals sultry deets! Featuring classic cap sleeves and a twisted open back design to flaunt some skin, and a bodycon silhouette that hugs your curves. Complete the look with a clutch for a dinner party!

    Fit & Features

    • Brushed knit fabric lined with stretchy knit
    • Crew neckline
    • Twisted open back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5754

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Flirty Eyelet Knit Skater Romper

    So flirty, this adorable eyelet knit skater romper is perf for weekend brunch. You'll love the fit-and-flare silhouette with hidden shorts for coverage.

    Fit & Features

    • Eyelet knit fabric
    • Sleeveless V-neckline, knot-front bust design
    • Spaghetti straps
    • High-rise waist
    • Mini-length overlay, skater silhouette
    • Hidden fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-1277

    Category Name: Vacation Looks

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Laid-Back Chic High Waist Shorts

    Give off a laid-back chic look for your weekend plans in these cute high waist shorts! Designed from a cozy ribbed sweater knit fabric, they feature a high-rise banded waist, a short-length hem, and a form-hugging fit. Style with the matching cropped sweater for the perf lounge vibe!

    Shop Matching Top: Laid-Back Chic Collared Cropped Sweater

    Fit & Features

    • High-rise banded waist
    • Short-length hem
    • Form-hugging fit
    • Ribbed sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06503-1114

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Summer Cherry Charm Necklace

    Create sweet looks this summer with this cherry charm necklace! 

    Fit & Features

    • Cherry charm
    • Dainty chain
    • Lobster clasp closure

    Style Number/Barcode: 07002-000070

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

    Product Badge:
    • Sale
  • Trendy Statement Platform Under-The-Knee Boots

    These of-the-moment platform boots will make a trendy statement this season! They feature an under-the-knee height with a simple pull-on design, a classic round toe, a chunky platform lug sole, and a short block heel. The boots are composed of a smooth matte jelly-like rubber material. Complete your cold-weather look with a plaid shacket!

    Fit & Features

    • Under-the-knee height
    • Pull-on design
    • Round toe
    • Platform lug sole
    • Short block heel
    • Matte rubber material
    • Runs true to size

    Style Number/Barcode: 07402-0986

    Category Name: Vacation Looks

    Price: $4.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Step Into Glam Rhinestone Sandals

    Step into glamour with these flat sandals. These eye-catching sandals feature two dazzling rhinestone-embellished bands that catch the light with every step.

    Fit & Features

    • Rhinestone-embellished two bands
    • Square toe
    • Flat sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-000033

    Category Name: Vacation Looks

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: In Stock

    Available Color: ROSE, GOLD, SILVER

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 10, 9

    Product Badge:
    • Sale
  • Desert Princess Halter Maxi Dress With Pockets

    Experience the effortless beauty of this boho maxi dress! The sleeveless halter neckline and spaghetti strap tie create a flowy silhouette, while the hidden side pockets add functionality. The front slit and ruffled maxi-length hem in a chic bohemian print will make you feel like a true desert princess! Complete the look in sandals and sunnies.

    Fit & Features

    • Bohemian print, woven fabric, no stretch
    • Halter neckline, spaghetti strap tie
    • Hidden side pockets
    • Flowy ruffled silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5804

    Category Name: Vacation Looks

    Price: $16.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Match Chevron Knit Tube Top

    Trend right with this chevron knit tube top for weekend fun or vacation! Pair with the matching skirt to complete the look.

    Fit & Features

    • Chevron pattern, stretchy knit lined fabric
    • Strapless neckline
    • Fitted crop hem
    • Runs true to size

    Shop The Matching Skirt: Trendy Match Chevron Knit Midi Skirt

    Style Number/Barcode: 06005-2254

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek And Sophisticated Satin Wide-Leg Pants

    Sleek and sophisticated, these satin wide-leg pants will stylishly elevate your look. They feature a high-rise waist, front pleating, a wide-leg silhouette, and a relaxed fit. The satin woven fabric has minimal stretch. Pair with a basic bodysuit and strappy mules.

    Fit & Features

    • High-rise waist, elasticized back waistband
    • Front pleated detailing
    • Wide-leg silhouette
    • Relaxed fit
    • Satin woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06402-1327

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale