Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

  • Trendsetting Vibes Oversized Square Sunglasses

    Show off those trendsetting vibes with these sleek shades! They feature a glam oversized design with a curved square shape, a thin metal frame, chain-link accents on the arms, rubber nose pads for support, and tinted lenses with a cool smokey brown hue. Style with hoop earrings.

    Fit & Features

    • Oversized design, curved square shape
    • Thin metal frame
    • Chain-link accents on the arms
    • Rubber nose pads
    • Smokey brown tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1026

    Category Name: Vacation Looks

    Price: $4.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Step Up Your Style Oversized Square Sunglasses

    Step up your summer style with these fab oversized sunglasses. They feature a square-shaped oversized design with a clear plastic frame, metal chain-link accents on the arms with mini rhinestone embellishments, and tinted lenses. Pair with a mini handbag.

    Fit & Features

    • Oversized square-shaped design
    • Clear plastic frame
    • Metal chain-link accents on the arms, mini rhinestones
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1027

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cancun Chica Tropical Satin Tie Front Top

    You'll be the cutest chica in this tropical satin top in Cancun! It features flowy kimono sleeves, a plunge V-neckline, a cropped hem, and customizable straps that can tie in the front or back. Style with trendy denim shorts and wedges to complete your vacay look!

    Fit & Features

    • Flowy kimono sleeves
    • Plunge V-neckline
    • Cropped hem
    • Customizable straps 
    • Tropical print
    • Silky satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1585

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Greek Key On Fleek Mesh Ruche Mini Skirt

    Look on fleek for vacationing in Greece or on a private yacht in this fab mesh Greek key print mini skirt! It features a high-rise elasticized waistband, bodycon silhouette, and a front ruched drawstring so you can customize the style and a bodycon fit. Style with a crop top and clear heel mules for a fabulous look.

    Fit & Features

    • High-rise elasticized waistband
    • Bodycon silhouette
    • Front ruched drawstring
    • Mini-length hem
    • Greek key print
    • Sheer mesh fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06501-0654

    Category Name: Vacation Looks

    Price: $11.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Let's Get Together Tie-Front Crop Top

    You and this crop top must get together soon! Start prepping for brunch under the sun in this sleeveless top featuring a sweetheart neckline, a tie-front design, spaghetti straps, a smocked back panel, and a fitted, cropped hem. Complete the look with the matching maxi skirt!

    Shop Matching Bottoms: Let's Get Together Tiered Maxi Skirt

    • Sleeveless sweetheart neckline
    • Tie-front design
    • Spaghetti straps
    • Smocked stretchy back panel
    • Fitted, cropped hem
    • Gauze fabric
    • Runs true to size

    Style Number/Barcode: 06003-1814

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Mood Ditsy Floral Mini Dress

    This adorable ditsy floral mini dress will have you in the mood for easy summer days! It features a sleeveless scoop neckline, a small bust cutout with a tie-front detail, spaghetti straps, a mini-length hem, and a form-hugging silhouette. The ditsy floral printed ribbed knit fabric offers plenty of stretch. Style with hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless scoop neckline
    • Small bust cutout, tie-front detail
    • Spaghetti straps
    • Mini-length hem, form-hugging fit
    • Ditsy floral print
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5114

    Category Name: Vacation Looks

    Price: $5.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Floral Vibes Ruched Mini Dress

    Capture a sweet romantic look in this flirty floral mini dress! It features a sleeveless V-neckline with ruching at the bust, spaghetti straps, a mini-length hem, and a form-hugging fit. The stretchy ribbed knit fabric features an all-over ditsy floral print for an adorable summer style. Pair with espadrille sandals for a day date.

    Fit & Features

    • Sleeveless V-neckline
    • Ruching at the bust
    • Spaghetti straps
    • Mini-length hem, form-hugging fit
    • Ditsy floral print
    • Ribbed knit fabric, smooth knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4760

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bold Strut Floral Lace-Up Block Heels

    Strut into your next party in bold style with these fabulous floral block heels! They feature an open square toe, a clear toe strap, a closed back, a thin lace-up strappy design that wraps around the leg, a sturdy block heel, and an all-over tropical floral print pattern that will catch everyone's attention. Complete the look with hoop earrings and a mini handbag.

    Fit & Features

    • Open square-shaped toe
    • Clear PVC toe strap
    • Closed back
    • Thin lace-up strappy design
    • Block heel
    • Tropical floral print
    • Runs true to size

    Style Number/Barcode: 07401-4427

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Gorgeous Getaway Tropical Print Midi Dress

    Get a gorgeous look for your next vacay getaway with this alluring tropical print midi dress. It features a sleeveless square neckline, spaghetti straps, an open back with a cross-back lace-up strappy design, ruching at the waist, a midi-length hem with an asymmetric high side slit, and a curve-hugging silhouette. The all-over palm leaf pattern on the stretchy knit fabric will bring those tropical vacation vibes. Style with cute wedges.

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Open back, cross-back lace-up strappy design, tie closure
    • Ruched detailing at the waist
    • Midi-length hem, asymmetric high side slit
    • Curve-hugging silhouette
    • Tropical palm leaf print, knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5008

    Category Name: Vacation Looks

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Time To Escape Tropical Print Maxi Dress

    Get ready to escape on a gorgeous getaway in this sultry tropical print maxi dress! It features a sleeveless asymmetric one-shoulder neckline with a spaghetti strap, a bold and alluring asymmetric waist cutout with a trendy O-ring accent, a hip-hugging fit that will hug your natural curves, and a floor-length hem with a thigh-high side slit to showcase some leg. The all-over palm leaf print on the stretchy knit fabric captures those tropical oasis vibes. Style with strappy sandals.

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline
    • Single adjustable spaghetti strap
    • Asymmetric waist cutout, O-ring accent
    • Hip-hugging fit, floor-length hem, high side slit
    • Tropical palm leaf print
    • Knit fabric, mini-length lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5016

    Category Name: Vacation Looks

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Style Refresh Low Block Heel Mules

    These chic low block heel mules are a fab style refresh! They feature an open square toe, a wide banded strap, an open back for easy on-and-off styling, and a low block heel. Complete your look with chunky hoop earrings and a mini handbag.

    Fit & Features

    • Open square-shaped toe
    • Wide banded toe strap
    • Open back, on-and-off styling
    • Low block heel
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-4223

    Category Name: Vacation Looks

    Price: $12.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fresh Summer Vibes Wrap-Front Romper

    Show off a fresh summer vibe in this elevated and chic woven romper. It features a sleeveless V-neckline, tank shoulder straps that lead to an open back with a cross-back lace-up design, a lower back cutout, a flattering high waist seam, a ruched wrap-front design with a short skirt overlay, and fitted shorts. Style with espadrille wedges for a cute daytime party look.

    Fit & Features

    • Sleeveless V-neckline
    • Tank shoulder straps
    • Open back, cross-back lace-up design, tie closure
    • Lower back cutout, zipper and hook-eye closure
    • High waist seam, ruched wrap-front, short skirt overlay, fitted shorts
    • Lined smooth woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06403-0330

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Daydream Ruffled Chiffon Maxi Dress

    You'll look like a stunning summer daydream in this airy chiffon maxi dress perfect for bridal showers or weekend outings! It features a V-neckline, short layered sleeves with a fluttery design, an open back with tie-back straps, a high waist silhouette, a faux button-down front leading to a chic slit, a floor-length hem with a ruffled seam, and a flowy, A-line fit. The sheer chiffon fabric includes a mini-length knit lining. Style with espadrille sandals.

    Fit & Features

    • V-neckline
    • Short layered sleeves, fluttery design
    • Open back, tie-back straps
    • High waist silhouette, stretchy smocked back detail
    • Faux button-down front, slit
    • Floor-length hem, ruffled seam, A-line fit
    • Sheer chiffon fabric, mini-length knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2335

    Category Name: Vacation Looks

    Price: $5.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Weekend Vibes One-Shoulder Midi Dress

    This sultry curve-hugging midi dress gives off major summer weekend vibes! It features an asymmetric one-shoulder neckline with dual adjustable spaghetti straps, an alluring open back with an asymmetric strap design, a midi-length hem, and a bodycon silhouette. The ribbed knit fabric offers plenty of stretch. Style with platform wedges for dinner and drinks.

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline
    • Dual adjustable spaghetti straps
    • Open back, asymmetric strap design
    • Midi-length hem
    • Bodycon fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5173

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Summer Stroll Strappy Platform Sandals

    These trendy platform sandals would be so cute for casual weekend strolls this summer season! They feature an open square toe, three straps across the foot with a puff design, an adjustable heel strap, and a flat platform sole. The faux leather material offers a soft, cushioned insole for comfort. Style with a crossbody bag.

    Fit & Features

    • Open square-shaped toe
    • Three straps across the foot, puff design
    • Adjustable heel strap, buckle detail
    • Flat platform sole
    • Faux leather material, soft cushioned insole
    • Runs true to size

    Style Number/Barcode: 07404-1147

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All About Basic Slit Tank Top

    Start with the basics. This sleeveless tank top is essential for building the perfect wardrobe! Featuring a square neck, wide straps, a form-fitting design, and trendy side slit accents along the cropped hem. Complete the look in high-rise jeans and sandals.

    Fit & Features

    • Sleeveless, square neck, wide straps
    • Form-fitting design
    • Side slit accents
    • Cropped hem
    • Double-layered modal fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4809

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flawless Double Take V-Neck Strappy Jumpsuit

    Look flawless always in this knit jumpsuit as people do double-takes whenever you walk by! It features a sleeveless V-neckline, dual spaghetti straps that create the strappy back design, and a wide-leg silhouette on smooth stretchy knit fabric. Complete the look in platform heels for a dinner out!

    Fit & Features

    • Sleeveless V-neckline
    • Dual spaghetti straps
    • Strappy back design
    • Wide-leg silhouette
    • Smooth, stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 06502-2345

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Somewhere Tropical V-Neck Midi Dress

    You deserve to go somewhere tropical with this midi dress as your inspiration! It features a sleeveless V-neckline, spaghetti straps, a curve-hugging silhouette, and a flirty slit hem. The dress is composed of a palm-printed stretchy knit fabric. Complete the look in strappy-heeled sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Curve-hugging silhouette
    • Slit midi-length hem
    • Palm print, stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4966

    Category Name: Vacation Looks

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ready For Sun Rib Knit Mini Dress

    Ready for some sun? Let this rib knit mini dress cue the sunshine! It features a sleeveless scoop neckline, a flirty bust tie with a keyhole accent, spaghetti straps, and a bodycon silhouette. Complete the look in trendy flat sandals for a backyard bbq!

    Fit & Features

    • Sleeveless scoop neckline
    • Bust tie, keyhole accent
    • Spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5149

    Category Name: Vacation Looks

    Price: $6.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Out Of Office Tropical Print Maxi Dress

    Packing this gorgeous tropical print maxi dress in your carry-on is a must for your vacay getaway! It features a sleeveless V-neckline with an O-ring accent at the bust, a sultry waist cutout at the front, adjustable spaghetti straps, a fitted, flowy, floor-length hem, and a thigh-high front slit. The smooth knit fabric showcases a tropical palm leaf print. Style with cute wedges.

    Fit & Features

    • Sleeveless V-neckline, center O-ring bust accent
    • Front waist cutout
    • Adjustable spaghetti straps
    • Fitted, flowy, floor-length hem, high front slit
    • Tropical palm leaf print
    • Knit fabric, short-length knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5015

    Category Name: Vacation Looks

    Price: $9.97 $43.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beautiful Blooms Floral Asymmetric Midi Dress

    Create a stunning summer date look with this beautiful blooming floral midi dress. It features a sleeveless V-neckline, spaghetti straps that lead to an adjustable cross-back design, ruching down the side seam, an asymmetric midi-length hem creating a thigh-high side slit, and a bodycon silhouette that will hug your curves. The smooth knit fabric features an all-over bold floral print pattern. Style with hoop earrings and strappy mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, adjustable cross-back design
    • Ruched side seam
    • Asymmetric midi-length hem, high side slit
    • Bodycon silhouette
    • Floral print, knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-1601

    Category Name: Vacation Looks

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 2000s Style Clear-Frame Sunglasses

    Amp up your trendy summer looks with these clear-frame sunglasses that bring that early 2000s style! They feature curved geometric-shaped lenses with a top metal bar accent, textured chain-link detailing on the arms, and rubber nose pads for support. Pair with a mini handbag.

    Fit & Features

    • Clear frame design
    • Curved geometric-shaped lenses
    • Top metal bar accent
    • Textured chain-link detailing on the arms
    • Rubber nose pads

    Style Number/Barcode: 07008-0998

    Category Name: Vacation Looks

    Price: $5.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirt On Check Linen Puff Sleeve Jumpsuit

    Your flirt will be in check with this linen jumpsuit perfect for your upcoming summer fun! It features adorable puff short sleeves, a surplice wrap sweetheart neckline, a stretchy smocked back,a cutout bodice, an elasticized high-rise waist, and a flattering wide-leg silhouette. Complete the look with chic sunglasses for a brunch or family bbq! 

    Fit & Features

    • Puff short sleeves
    • Surplice wrap sweetheart neckline
    • Stretchy smocked back
    • Cutout bodice
    • Elasticized high-rise waist
    • Wide-leg silhouette
    • Linen fabric, sewn-in knit bust lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0770

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Remy High-Rise Vintage Wash Shorts By Windsor Denim

    Bring the cool looks for summer in the must-have Remy high-rise shorts by Windsor denim! They feature a flattering fit and feel with trendy distressed accents and a frayed cut-off hem. The jean shorts are composed of vintage-inspired medium-wash denim fabric. Complete the look in a crop denim jacket for a 90s throwback vibe!

    Fit & Features

    • High-rise waist
    • Distressed accents
    • Frayed cut-off hem
    • Vintage-inspired medium-wash denim, no stretch
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Runs true to size

    Style Number/Barcode: 06603-0250

    Category Name: Vacation Looks

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free