Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

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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.

  • Social Girlie High Rise Slit Midi Skirt

    Your social calendar is filling up and this midi skirt is here to help! Featuring a high-rise waist, side adjustable drawstring, and bodycon fit, this skirt will accentuate your curves and flatter your figure. The high-side asymmetrical slit adds a touch of intrigue while the midi-length hem keeps it chic. Complete the look in sandals.

    Fit & Features

    • Smooth knit stretchy fabric
    • High rise waist
    • Bodycon fit
    • Adjustable drawstring
    • Asymmetrical high side slit
    • Runs true to size

    Style Number/Barcode: 06501-1039

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ocean Breeze Cowl Neck Low Back Tropical Maxi Dress

    Relax poolside with a drink in hand and this tropical mesh maxi dress on! Featuring a playful cowl neckline, adjustable spaghetti straps, and a low back with criss-cross straps for a touch of intrigue. Its curve-hugging silhouette and maxi-length hem will make you feel like a tropical goddess on vacation! Complete the look in sunnies and sandals!

    Fit & Features

    • Tropical palm print, mesh fabric lined with stretchy knit
    • Cowl neckline
    • Adjustable spaghetti straps
    • Low back with criss-cross straps
    • Curve-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5645

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Resort Calling Mesh Slit Maxi Skirt

    Booked the trip? This skirt is already packed. Featuring a high-rise waist and dramatic slit skirt, this floral mesh moment is giving vacation muse energy—made for poolside lounges or rooftop cocktails.

    Shop The Matching Top: Resort Calling Mesh Tie Front Top

    Fit & Features

    • Floral print, attached panty knit lining
    • High-rise waist
    • High front slit
    • Flowy maxi length hem
    • Runs true to size

    Style Number/Barcode: 06501-000037

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Summer Pick Gingham Halter Crop Top

    The cutest gingham crop top for any summer day! Look and feel so cute in this top with a pretty open back with tie-back details and a ruffled crop hem to show off your figure.

    Fit & Features

    • Gingham print, woven fabric
    • Plunge halter neckline, spaghetti strap tie
    • Ruffled crop hem
    • Open back, tie-back details
    • Runs true to size

    Style Number/Barcode: 06003-000072

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: S, M, L

  • Cute Sight Cateye Metal Sunglasses

    This pair of sunglasses features a cateye design on a sleek metal frame, tinted lenses with 100% UV protection, and rubber nose supports. Perfect for everyday styling.

    Fit & Features

    • Cateye design, sleek metal frame
    • Tinted lenses
    • 100% UV protection
    • Rubber nose supports

    Style Number/Barcode: 07008-1105

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Muse Floral Maxi Dress

    Beach date or rooftop night out? You’re covered. With a drapey neckline and bold floral print, this maxi gives you that effortless she’s glowing moment.

    Fit & Features

    • Floral print, mesh fabric lined with stretchy knit
    • Cowl halter neckline
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000273

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Resort Ready Eyelet Linen Platform Block Heels

    Elevate your spring-to-summer looks in these eyelet linen platform block heels, perfect for a resort vacation or weekend event.

    Fit & Features

    • Block heel
    • Square toe, criss cross toe strap
    • Platform sole
    • Luxe fit cushioned insole
    • Adjustable ankle strap, buckle closure
    • Eyelet linen material
    • Runs true to size

    Style Number/Barcode: 07401-5274

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: 7, 7.5, 8, 8.5, 9

  • Flirty Moves Ruffled Tie-Front Knit Crop Top

    Make major flirty moves and create an enticing aura in this ruffled tie-front crop top! Designed with a stretchy smooth knit fabric, it features a sultry V-neckline with a tie-front design, ruffled hems for that girly flair, spaghetti straps, and an asymmetric cropped hem. Style with the matching midi skirt for a girl's night out!

    Shop Matching Bottoms: Flirty Moves Ruffled Slit Knit Midi Skirt

    Fit & Features

    • Double-lined stretchy smooth knit fabric
    • V-neckline, tie-front design
    • Ruffled hems
    • Spaghetti straps
    • Asymmetric cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5451

    Category Name: Vacation Looks

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Seamless Sculpt Bandeau Bra

    A bandeau bra designed to stretch with your body while offering a seamless and sculpting fit. This bra features a strapless neckline for no-fuss wear, removable padded bra cups that shape and support, and a seamless design on buttery smooth knit fabric. Style this bandeau with smooth shapewear shorts for a sleek silhouette.

    Fit & Features

    • Seamless, buttery smooth knit fabric
    • Strapless neckline
    • Removable padded bra cups
    • Runs true to size 

     

    Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07102-0327

    Category Name: Vacation Looks

    Price: $7.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirt On Arrival Denim Skater Dress

    Made for flings, flirts, and feelin’ yourself. This trendy halter skater dress hugs you in all the right places with a playful bust cutout and a twirl-worthy drop waist—aka your weekend wardrobe’s new fave.

    Fit & Features

    • Denim fabric
    • Sleeveless cross-front halter neckline, tie-back straps
    • Bust cutout, metal heart accent
    • Partially open back, hidden lower back zipper closure
    • Drop waist
    • Short pleated skater silhouette
    • Runs small, size up recommended

    Style Number/Barcode: 05102-000084

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: DENIM

    Available Size: S, M

  • Pretty Style Beaded Stretch Bracelet Set

    Adorn your wrist with this pretty and stylish bracelet set! It features three stretchy bracelets with varying sleek beaded designs. Complete the look with trendy sandals for any occasion or plan!

    Fit & Features

    • Three stretchy bracelets
    • Varying beaded designs

    Style Number/Barcode: 07003-0572

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Want To Want Me Floral Crochet Tie Front Top

    Wrap yourself in the bohemian charm of this floral crochet top! With kimono half sleeves and a tie-front design, this top is perfect for adding a touch of boho vibes to any outfit.

    Fit & Features

    • Sheer floral crochet knit fabric
    • Kimono half sleeves
    • Tie-front
    • Crop hem
    • Runs true to size

    Style Number/Barcode: 06204-000010

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Pretty Bold One-Shoulder Floral Mesh Crop Top

    Pretty and bold, this sleeveless crop top features a one-shoulder neckline, an adjustable side drawstring, and an asymmetrical-cut hem. The mesh fabric showcases a bold floral print.

    Fit & Features

    • Floral print, mesh fabric lined with mesh, stretchy
    • One-shoulder neckline
    • Adjustable side drawstring
    • Asymmetrical-cut cropped length hem
    • Runs true to size

    Style Number/Barcode: 06001-5482

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Match Sleeveless Striped Ribbed Knit Mini Dress

    You and this striped knit mini dress are the perfect match for sunny days! With a playful scoop neckline and cutout back, this mini dress is a cute piece for any fun occasion. Its bodycon fit flatters your figure while the striped pattern adds a touch of quirkiness. The ribbed knit fabric offers a moderate stretch for comfortable wear. Complete the look with flat sandals.

    Fit & Features

    • Striped pattern
    • Ribbed knit fabric with moderate stretch
    • Scoop neckline
    • Tank shoulder straps
    • Cutout back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1940

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • You've Got Flare Halter Cutout Wide Leg Jumpsuit

    Featuring a flattering halter neckline and playful cutout details, this jumpsuit combines trendiness with a touch of boldness. The wide-leg silhouette and ruffled accents create a flowy look that moves with you.

    Fit & Features

    • Woven fabric
    • Halter plunge neckline, spaghetti strap tie
    • Cutout bodice with drawstring tie
    • Ruffled wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06302-000004

    Category Name: Vacation Looks

    Price: $54.90

    Availability: In Stock

    Available Color: OLIVE

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Endless Vacay High Rise Wide-Leg Trouser Pants

    Get ready for vacay packing these trouser pants for endless fun under the sun! Whether you're island hopping in Greece or sipping a mai tai on the beach, these pants will keep you so trendy. It boasts a flattering high-rise waist with side pockets for keeping your hands warm, a breeze wide-leg silhouette, plus a button front and hidden zipper closure to secure the style. Complete the look with the matching top.

    Shop Matching Top: Endless Vacay Strapless Tube Crop Top

    Fit & Features

    • Texture woven fabric
    • High-rise waist
    • Wide-leg silhouette
    • Side pockets
    • Front button and hidden zipper closure
    • Runs true to size

    Style Number/Barcode: 06402-1405

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ring Me Up Strapless Romper

    Built-in beach club energy. This strapless romper brings the heat with a keyhole O-ring detail and a cinched waist that flatters every curve—perfect for hot days, hotter nights, and bottomless brunches.

    Fit & Features

    • Woven fabric, stretchy knit shorts lining
    • Sweetheart strapless neckline, hoop insert, cutout
    • Back zipper and hook-eye closure
    • Fitted cinch bodice
    • Runs true to size

    Style Number/Barcode: 06303-000027

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Whimsical Cutie Butterfly Polka Dot Satin Maxi Dress

    Soar toward any celebration in this whimsical and cute polka dot satin maxi dress! Featuring cap sleeves and a gorgeous butterfly lace trim sweetheart neckline, this dress adds a touch of elegance. The button-down back with a cutout accent completes the maxi silhouette, making you the center of attention! Complete the look in strappy block heels and a necklace.

    Fit & Features

    • Polka dot print, satin fabric, no stretch
    • Butterfly lace trim sweetheart neckline
    • Button-down back and zipper hook-eye closures
    • Cutout back accent
    • Maxi length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3555

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picture Perfect V-Neck Smocked A-Line Midi Dress

    You'll be the picture of perfection in this adorable A-line midi dress at showers or birthday brunch! With its flattering V-neckline and stretchy smocked bodice, this dress hugs your body in all the right places. The tie spaghetti straps add a touch of delicacy, while the V-cut waist seam and A-line silhouette create a flattering look along the midi-length hem. Complete the look in espadrille wedges.

    Fit & Features

    • Woven fabric lined with non-stretch woven
    • Tie spaghetti straps
    • V-neckline
    • Stretchy smocked bodice
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3560

    Category Name: Vacation Looks

    Price: $11.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Make Hearts Flutter Short Sleeve Cutout Maxi Dress

    You'll instantly be crushing on this maxi dress perfect for weekend dinner parties or vacation! The flutter sleeves and plunging neckline create a playful vibe, while the elasticized waist and side cutouts show a hint of skin along the flowy maxi-length silhouette. Complete the look in strappy sandals.

    Fit & Features

    • Gauze woven fabric, short knit stretchy lining
    • Flutter short sleeves
    • Plunge V-neckline and V-cut back
    • Elasticized strappy waist with side cutouts
    • Flowy maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5719

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Coastal Breeze Linen High Slit Maxi Skirt

    Channel that coastal chic vibe with this breezy linen maxi skirt featuring a tiered design, high-cut side slit, and flowy A-line silhouette.

    Fit & Features

    • Linen-blend fabric
    • High-rise waist
    • Tiered design
    • Thigh-high side slit
    • Flowy A-line silhouette
    • Runs true to size

    Style Number/Barcode: 06301-000004

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: M, L

    Product Badge:
    • Best Seller
  • Living Sleek Square Chain Trim Sunglasses

    Keep your outfit sleek and trendy in these sunglasses perfect for any sunny day! They feature angled square tinted lenses, rubber nose supports, and chain link trim arms for an edgy flair. Complete the look in sandals.

    Fit & Features

    • Angled square tinted lenses
    • Rubber nose supports
    • Chain link trim arms

    Style Number/Barcode: 07008-1091

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Talkin' Flirty Halter Floral Bodycon Mini Dress

    Get ready to turn heads in this mesh mini dress! The ruffled floral trim halter neckline adds a touch of elegance, while the bodycon silhouette and mini-length hem accentuate your curves.

    Fit & Features

    • Mesh-lined fabric
    • Ruffled floral trim halter neckline, spaghetti strap tie
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000108

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: LIGHT, BLUE, BLACK

    Available Size: M, L, S

  • To The Sky Boho V-Waist Tie Flare Pants

    A boho-inspired print adds carefree charm to these flare pants perfect for festivals, concerts, or daytime adventures! Made with soft brushed knit fabric, these boho pants will keep you comfortable and stylish all day long. The high-rise V-waist and adjustable scrunch tie create a flattering, hip-hugging fit, while the flared hem adds a touch of playful movement. Complete the look in a cute crop tee and platform shoes.

    Fit & Features

    • Boho print, brushed knit stretchy fabric
    • High-rise V-waist, adjustable scrunch tie
    • Hip-hugging fit
    • Flared hem
    • Runs true to size

    Style Number/Barcode: 06502-2466

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale