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.

  • Booked And Unbothered Leopard Oversized Sunglasses

    These oversized sunglasses bring instant glam with a bold frame that was made for poolside posing and low-key paparazzi moments.

    Fit & Features

    • Oversized leopard frames with metal trim
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000009

    Category Name: Vacation Looks

    Price: $11.90

    Availability: In Stock

    Available Color: LEOPARD

    Available Size: NS

  • Weekend Vibes High Slit Striped Knit Maxi Dress

    This casual-chic striped knit maxi dress is perfect for your laid-back weekend vibes! Designed with stretchy ribbed knit with a thin striped pattern, it features a sleeveless scoop neckline with spaghetti straps, high-cut side slits on each side for added movement, and a form-hugging slim fit on the maxi-length silhouette. Style this long dress with strappy sandals.

    Fit & Features

    • Striped ribbed knit fabric, short knit lining, moderate stretch
    • Scoop neckline
    • Spaghetti straps
    • High side slits
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5778

    Category Name: Vacation Looks

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lovely Look Cold Shoulder Bodycon Lace Mini Dress

    Nothing can compare to your lovely look in this lace mini dress as a stunning bride-to-be or birthday girlie! Featuring a trendy cold shoulder V-neckline, feminine flutter short sleeve cuffs, and delicate spaghetti straps, this dress hugs your curves for a bodycon fit that will turn heads. Complete the look with earrings and clutch.

    Fit & Features

    • Lace fabric lined with stretchy knit
    • Cold shoulder V-neckline
    • Flutter short sleeve cuffs, spaghetti straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3423

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Crush Striped Crochet Bralette Top

    POV: you just found your new fave beach-to-brunch vibe. This striped crochet bralette top serves laid-back heat with an open back and tie details made for turning heads from sunrise to sunset.

    Shop Matching Bottoms: Summer Crush Striped Crochet Midi Skirt

    Fit & Features

    • Crochet knit fabric
    • Striped pattern
    • Sleeveless triangle bust design
    • Thin shoulder straps
    • Open back, tie-back design
    • Fitted ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-000034

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Flow My Way Chiffon Lace Trim Skater Dress

    Effortlessly flow into any occasion in this simply chic chiffon skater dress - the perfect style for bridal showers, graduates, and birthday girls! The dress features a cold shoulder V-neckline with a delicate scalloped lace trim, adjustable spaghetti straps, short-sleeve cuffs, and a flattering fit-and-flare short-length silhouette. The airy chiffon fabric includes a stretchy knit lining. Complete the look with a sleek choker and earrings.

    Fit & Features

    • Cold shoulder design, V-neckline, scalloped lace trim
    • Adjustable spaghetti straps, short-sleeve cuffs
    • Back zipper and hook-eye closure
    • Fit-and-flare skater silhouette
    • Short-length hem
    • Airy chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2053

    Category Name: Vacation Looks

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Favorite Strapless Cutout Floral Maxi Dress

    Create a stunning aurora in this floral maxi dress for summer cocktail hours! The strapless neckline and side cutout provide a flattering silhouette, while the form-hugging fit accentuates your curves, and the high side slit offers a show of leg. Complete the look in strappy stiletto heels.

    Fit & Features

    • Floral print, mesh fabric lined with stretchy knit
    • Strapless neckline
    • Side cutout
    • Form-hugging fit
    • High side slit
    • Runs true to size

    Style Number/Barcode: 05101-3278

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Yacht Babe Floral Swim Cover Up

    Soak up the sun looking like a babe in this swim cover-up! Wrap yourself in the beauty of summer with this long cover-up with a gorgeous floral print and a maxi form-hugging silhouette.

    Fit & Features

    • Floral print, sheer mesh stretchy fabric
    • Low-rise waist, side cutouts
    • Form-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 07105-000014

    Category Name: Vacation Looks

    Price: $10.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfectly Glam Rhinestone Butterfly Spiral Strap Sandals

    Create a perfectly glam vibe with these rhinestone butterfly strappy sandals! Designed with sleek faux leather, they feature an almond-shaped toe, a dual toe strap and trendy spiral strap design, mini rhinestone embellishments for that glitzy shine, and organza butterfly accents with rhinestone detailing. They include a flat sole with a padded insole for comfortable wear. Style with a summer party dress!

    Fit & Features

    • Faux leather upper
    • Almond toe
    • Dual toe strap and spiral strap design
    • Mini rhinestones
    • Sheer organza butterfly accents with rhinestones
    • Flat sole, padded insole
    • Runs true to size

    Style Number/Barcode: 07406-0362

    Category Name: Vacation Looks

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sun-Kissed Moments Triangle Bikini Top

    You'll have sun-kissed moments in this trendy triangle bikini top featuring the cutest seashell charm at the center of the bust. Style with the matching bikini bottoms.

    Shop Matching Bottoms: Sun-Kissed Moments Tie-Strap Bikini Bottoms

    Fit & Features

    • Nylon-blend fabric, high stretch
    • Triangle-shaped cups
    • Seashell metal charm
    • Adjustable spaghetti straps
    • Tie-back spaghetti straps, beaded details
    • Runs true to size

    Style Number/Barcode: 07104-000006

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simply Adorable Puff Sleeve Cutout Crop Top

    Simply adorable, this puff sleeve cutout crop top will effortlessly elevate your casual 'fits. The smooth knit fabric offers a lightweight feel and plenty of stretch. The top features a ruched V-neckline, short puff sleeves with elasticized hems, and a bold front cutout below the bust. The open lower back is accented with an adorable tie-back design. Style this fitted top with high-rise jeans and strappy mules.

    Fit & Features

    • Stretchy knit fabric, double-lined front
    • Ruched V-neckline
    • Short puff sleeves
    • Front cutout
    • Open lower back, tie-back design
    • Cropped, fitted
    • Runs true to size

    Style Number/Barcode: 06001-5329

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stackable Style Seven Pack Ring Set

    The perfect seven-pack ring set to achieve stackable style! This set features an assortment of various designs and styles with glitzy rhinestone embellishments that bring some sparkle to your look. Complete the look with a chic handbag for any occasion!

    Fit & Features

    • Seven-pack ring set
    • Rhinestone embellishments
    • Various designs and styles

    Style Number/Barcode: 07004-0399

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • You Love Me Graphic Tank Top

    Unapologetically bold and playful, this graphic tank top is a must-have for those who want to make a statement. Featuring a cropped design and eye-catching "You Look Like You Love Me" graphic, this tank top exudes attitude.

    Fit & Features

    • Stretchy rib knit fabric
    • Crew neck
    • Racerback design
    • "You Look Like You Love Me" graphic script
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-000072

    Category Name: Vacation Looks

    Price: $18.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, M, L

  • Crusin' The Tropics Lace-Up Tropical Mini Dress

    Cruise the tropics in this stylish tropical mini dress! Designed with a tropical palm print on knit fabric, this dress is sure to stand out on the island and boat. Featuring a V-neckline and spaghetti straps, a lace-up back that lets you customize the style, and a flattering bodycon fit. Complete the look with sunglasses.

    Fit & Features

    • Tropical palm print, stretchy knit fabric, sewn-in lining
    • Spaghetti straps
    • V-neckline
    • Lace-up back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5549

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Walk In The Park Eyelet Lace-Up Espadrille Wedges

    From brunch to a day at the park, these wedges will keep you comfortable and stylish all day long. Featuring a delicate eyelet design and a lace-up ankle strap, these espadrille wedges are perfect for adding a touch of cuteness to any outfit.

    Fit & Features

    • 4" Wedge heel
    • Closed almond toe with eyelet inset
    • Lace-up ankle strap
    • Espadrille material
    • Runs true to size

    Style Number/Barcode: 07406-000012

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: 6.5, 10

  • Outside The Lines Tie Back Slit Marble Maxi Dress

    Color outside the lines and rock this chic marble print maxi dress for dressy showers or summer events! With a square neckline and spaghetti straps, this dress flatters your figure with a form-hugging fit. The tie-back design adds a touch of unique style while the front slit showcases your legs along the maxi-length hem. Complete the look with earrings and heels.

    Fit & Features

    • Marble print, smooth knit fabric with stretchy lining
    • Spaghetti straps
    • Square neckline
    • Tie back design
    • Form-hugging fit
    • Front slit
    • Runs true to size

    Style Number/Barcode: 05101-3455

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Ways Halter Lace Trim Crop Top

    With this flirty crop top for celebrations or date night, you'll stun in the plunge halter V-neckline with a dainty lace trim and partially open back. Pair with the matching skirt to complete the look.

    Shop Matching Bottoms: Flirty Ways Ruched High Slit Midi Skirt

    Fit & Features

    • Double-lined stretchy knit fabric
    • Plunge halter V-neckline, lace trim, tie closure
    • Partially open back
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-000094

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Constant Sensation V-Neck Corset Satin Skater Dress

    Always be a constant sensation when you step out in this satin skater dress at parties or soirees! With a flirty V-neckline, comfortable shoulder straps, and a flattering corset-seam bodice, this dress has a playful skater silhouette and a short-length hem. The abstract print adds a touch of fun to the satin fabric. Complete the look with bracelets and a clutch!

    Fit & Features

    • Abstract print, satin fabric, woven lining, no stretch
    • V-neckline, shoulder straps
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3291

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Symphony Floral Maxi Skirt

    This floral maxi skirt brings perfect tropical vibes to your weekend plans or vacation! Pair with the matching top to complete the look.

    Shop Matching Top: Perfect Symphony Floral Tube Top

    Fit & Features

    • Floral print, chiffon fabric, stretchy knit lining
    • High-rise waist
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000043

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Sunshine On My Mind Strapless Tropical Skater Dress

    This tropical skater dress will inspire sunshine on your mind! Perfect for vacations or a beach day, this strapless dress features a stretchy waist leading to the skater silhouette and a flirty ruffled mini-length hem. Complete the look in espadrille wedges.

    Fit & Features

    • Tropical palm print, gauze woven fabric, bust lining
    • Strapless neckline
    • Skater silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5744

    Category Name: Vacation Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • By The Beach V-Neck Halter Babydoll Crop Top

    Enjoy a sunny day by the beach in this breezy babydoll crop top with a pretty eyelet V-neckline and a flowy silhouette. Perfect for styling as a cover-up or by itself.

    Fit & Features

    • Cotton woven fabric
    • Adjustable spaghetti straps
    • V-neckline, eyelet bust
    • Stretchy smocked back panel
    • Flowy uneven crop hem
    • Runs true to size

    Style Number/Barcode: 06003-2763

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: L

  • Sweet Silhouette Rosette Ruffled Knit Mini Dress

    The knit mini dress features a sleeveless scoop neckline accented with a dainty rosette detail for an adorable touch. The tiered ruffled mini-length hem and bodycon fit add a flirty feel while highlighting your curves.

    Fit & Features

    • Ribbed knit fabric with knit lining, plenty of stretch
    • Scoop neckline with rosette detail
    • Spaghetti straps
    • Tiered ruffled mini-length hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5846

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blooming Beauty Floral Print Mesh Maxi Dress

    Let your beauty bloom with a mesh maxi dress that features a sleeveless sweetheart neckline with lace trim, a bodycon-fit silhouette, and a pretty floral print throughout! Complete your date night look with stiletto heels! 

    Fit & Features

    • Sheer mesh fabric with knit lining, plenty of stretch
    • Floral print
    • Sleeveless sweetheart neckline, lace trim
    • Spaghetti straps
    • Bodycon-like fit
    • Long maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3785

    Category Name: Vacation Looks

    Price: $44.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Party Diva Cropped Rhinestone Halter Top

    A cropped rhinestone halter top that'll inspire your next going-out look! It features a sultry plunge cowl neckline and a partially open back that turns heads. Pair with jeans.

    Fit & Features

    • Sheer mesh fabric with knit lining, moderate stretch
    • Studded rhinestones
    • Plunging halter neckline, cowl bust
    • Mini bar strap at bust
    • Halter neck ties, partially open back 
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5498

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: NUDE, BURGUNDY

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Blissful Afternoons Corset A-Line Midi Dress

    Enjoy an afternoon of bliss looking so sweet in this A-line midi dress at showers or semi-formal weddings! The sweetheart neckline and adjustable spaghetti straps accentuate your figure while the corset bodice with built-in padded underwire bust provides support. The flowy A-line silhouette and midi-length hem add elegance to your look. Complete the look in strappy heeled sandals.

    Fit & Features

    • Woven fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Sweetheart neckline
    • Corset bodice, built-in padded underwire bust
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3309

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale