Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

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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.

  • Soak Up The Rays O-Ring Bikini Top

    Get ready to soak up the rays in this triangle bikini top with O-ring insets and a flirty knotted bust. Pair with the matching bikini bottoms.

    Fit & Features

    • Lined knit fabric
    • Knotted bust, removable padded bra cups
    • Spaghetti straps
    • Back hook closure
    • O-ring insets
    • Runs true to size

     

    Shop The Matching Bikini Bottoms: Soak Up The Rays O-Ring Bikini Bottoms

    Style Number/Barcode: 07104-0723

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Destination Vacay Tropical Floral Mini Dress

    Jet set to your destination vacay in this tropical floral print mini dress, perfect for sunset happy hour. Designed with a square neck, adjustable spaghetti straps, and a short fitted silhouette, style with gold hoops and slide-on sandals.

    Fit & Features

    • Scuba knit fabric, stretchy knit lining
    • Tropical floral print
    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Back zipper closure
    • Mini-length fitted silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6077

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropical Vacay High-Rise Slit Midi Skirt

    The perfect tropical floral midi skirt to look stylish on your vacay! With its high-rise waist and cheeky panty lining, this skirt offers a comfortable fit and sleek silhouette. The high front slit and eye-catching tropical floral print add a touch of boldness to your look. Pair with the matching crop top and espadrille wedges!

    Shop Matching Top: Tropical Vacay Spaghetti Strap Tie-Back Crop Top

    Fit & Features

    • Tropical floral print
    • Stretchy knit fabric, cheeky panty lining
    • High-rise waist
    • High front slit
    • Midi-length
    • Runs true to size

    Style Number/Barcode: 06501-1010

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vibrant Side Geometric Print Bodycon Midi Dress

    Unleash your vibrant side in this stunning geometric midi dress on vacation, during weekend getaways, or at pool parties! Designed with a smooth knit fabric that effortlessly hugs your curves, it features a halter V-neck, open back, and center front slit for a trendy allure.

    Fit & Features

    • Smooth knit fabric, high stretch
    • Geometric tropical print
    • Sleeveless halter surplice V-neckline, open back
    • Ruching
    • Center front slit accent
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3929

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS

    Product Badge:
    • Sale
  • Sunshine Check Strappy Straw Denim Block Heels

    When the sun is shining, these denim block heels come out! It's open-toe season and these heels are a must-have for vacations or strolling downtown. They feature a square toe and straw denim strappy design, a sturdy block heel, and a closed ankle with an adjustable strap and buckle closure. Complete the look with a crossbody purse.

    Fit & Features

    • 4" Block Heel
    • Square toe
    • Denim straw strappy design
    • Closed ankle
    • Adjustable ankle strap with buckle closure
    • Runs true to size

    Style Number/Barcode: 07401-4882

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Days A-Line Midi Tube Dress

    Effortless days call for this woven midi tube dress designed with a smocked bodice with a geometric pattern and a flowy pleated A-line silhouette. Perfect for weekend plans, style with strappy sandals.

    Fit & Features

    • Poplin cotton woven fabric
    • Strapless sweetheart neckline
    • Smocked bodice, geometric pattern
    • High-rise waist
    • Side pockets
    • Midi-length pleated A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000007

    Category Name: Vacation Looks

    Price: $11.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ocean Dreams Seashell Mesh Bikini Bottoms

    Get beach-ready in these mesh bikini bottoms. The adjustable side ties ensure your perfect fit, while the seashell trim adds a touch of beachy glamour. Pair with the matching bikini top!

    Shop Matching Top: Ocean Dreams Seashell Mesh Bikini Top

    Fit & Features

    • Mesh-lined fabric
    • High-rise waist
    • Adjustable side ties with seashell trim
    • Cheeky coverage
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000004

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Trend Oversized Cateye Sunglasses

    A pair of sleek, trendy sunglasses featuring an oversized cateye design, tinted lenses with 100% UV protection, and nose supports. Perfect for everyday wear.

    Fit & Features

    • Oversized cateye design
    • Tinted lenses
    • 100% UV protection
    • Nose supports

    Style Number/Barcode: 07008-1104

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charmed Intent Bow Sandals

    No one can ignore the cute vibes of these bow sandals perfect for parties or graduations!

    Fit & Features

    • Square toe
    • Wide strap with statement bow
    • Flat sole
    • Padded insole
    • Patent faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1272

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: 5.5, 6.5, 7

    Product Badge:
    • Sale
  • Gone Coastal Snake Side Tie Bikini Bottoms

    If you're heading on vacay or the beach, these snake bikini bottoms will keep you fiercely stylish on and off the shore! Pair with the matching bikini top.

    Fit & Features

    • Snake print, lined fabric
    • Low-rise waist
    • Spaghetti strap side ties
    • Cheeky coverage
    • Runs true to size
    • Returns are not accepted without the hygienic liner

     

    Shop The Matching Bikini Bottoms: Gone Coastal Snake Triangle Bikini Top

    Style Number/Barcode: 07105-0873

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: In Stock

    Available Color: SNAKE

    Available Size: L

    Product Badge:
    • Sale
  • Floral Retreat Lace Up Embroidered Skater Dress

    Indulge in the ultimate feminine look in this floral skater dress for parties and dressy occasions! Featuring a delicate V-neckline, spaghetti straps, and a figure-flattering lace-up design, this dress is perfect for any event. The skater silhouette and short-length hem add a touch of playfulness, while the intricate floral embroidery adds a romantic and elegant touch. Complete the look in fringe earrings and heels!

    Fit & Features

    • Floral embroidery, mesh fabric lined with stretchy knit
    • Spaghetti straps
    • Lace up
    • Skater silhouette
    • Sticky bra or pasties recommended
    • Runs true to size

    Style Number/Barcode: 05101-2931

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy Bombshell One-Shoulder Bikini Top

    Beachy bombshell will be your vibe in this one-shoulder bikini top designed with lurex knit fabric for a trendy metallic sheen. Pair with the matching bikini bottoms and sarong for a sun-kissed look!

    Shop Matching Set: Beachy Bombshell Bikini Top, Beachy Bombshell V-Cut Bikini Bottoms, Beachy Bombshell Short Sarong

    Fit & Features

    • Lurex knit fabric, metallic sheen
    • One-shoulder asymmetric strap
    • Sweetheart padded bust with ruching, removable padded bra cups
    • Back hook and bar closure
    • Runs true to size

    Style Number/Barcode: 07104-0725

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: M, L

    Product Badge:
    • Sale
  • Adorable Confidence Floral Jacquard Skater Dress

    Let everyone know you've got the perfect style in this floral jacquard skater dress! Crafted from a jacquard floral embroidery, this dress exudes chic vibes. The ruffle trim sweetheart neckline and tie spaghetti straps add a touch of femininity, while the flexible boning ensures a perfect fit. The skater silhouette and short-length hem will have you twirling! Complete the look in strappy heels.

    Fit & Features

    • Floral jacquard embroidery, woven fabric, chiffon lining
    • Tie spaghetti straps
    • Ruffle trim sweetheart neckline
    • Back zipper and hook-eye closure
    • Flexible boning
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3166

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Sensation Lace A-Line Mini Dress

    A sweetly sensational lace A-line mini dress for chic brides-to-be, birthday girls, or graduates!

    Fit & Features

    • Lace-lined fabric
    • V-neckline
    • Adjustable spaghetti straps
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3982

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Always Sunny Strapless Ruffle Eyelet Mini Dress

    This eyelet mini dress is perfect for any sunny day and will be a favorite for shower celebrations, brunch, or graduations! The dress boasts a stretchy smocked bodice that hugs your figure while the ruffled mini-length hem adds a flirty allure.

    Fit & Features

    • Eyelet woven-lined fabric
    • Strapless neckline
    • Stretchy smocked bodice
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4019

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE, LIGHT, BLUE

    Available Size: M, L, XXS, XS, S

    Product Badge:
    • Sale
  • Sunny And Sweet Off-The-Shoulder Floral Crop Top

    Nothing's sweeter than a sunny day spent in this floral crop top! Featuring a ruffle trim neckline, short puff sleeves, and a stretchy smocked bodice, this top is as comfortable as it is stylish. The ruffled crop hem and floral print knit fabric add cuteness to any outfit. Complete the look in trendy denim shorts.

    Fit & Features

    • Floral print knit fabric, moderate stretch
    • Off-the-shoulder ruffle trim neckline
    • Short puff sleeves
    • Stretchy smocked bodice
    • Ruffled crop hem
    • Runs true to size

    Style Number/Barcode: 06001-5337

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blissful Cutie Halter Cutout Skater Dress

    Get swept off your feet in this cute skater dress for any casual occasion! With its halter neckline and cutout bodice, this dress is designed to show off your figure, while the ruffled mini-length hem adds a flirty touch.

    Fit & Features

    • Gauze woven fabric, woven lining
    • Halter neckline with spaghetti strap ties
    • Stretchy smocked bust
    • Cutout bodice
    • Ruffled skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6017

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: YELLOW, BLUE

    Available Size: M, L, XS, S

    Product Badge:
    • Sale
  • Cutie Vibe Gingham Print Thong Strap Sandals

    You'll love the cute vibe these thong strap sandals bring to your weekend 'fits! The adorable gingham print is a spring and summer staple.

    Fit & Features

    • Faux leather material
    • Gingham print
    • Almond-shaped toe
    • Thong strap design
    • Open back, on-and-off styling
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1249

    Category Name: Vacation Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: In Stock

    Available Color: PINK, RED, BLUE

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

    Product Badge:
    • Sale
  • Flawless Floral High Rise Wide-Leg Satin Pants

    You can't go wrong stepping out in this floral satin pants on a getaway or having a sunset dinner! Show off your fashion sense with these pants with a flattering high-rise waist, wide-leg detail, and a dainty floral print. Complete the look with the matching top.

    Shop Matching Top: Flawless Floral Kimono Tie-Front Satin Crop Top

    Fit & Features

    • Dainty floral print, satin fabric, no stretch
    • High-rise waist, back elastic waistband
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06402-1393

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Glow Floral Satin Maxi Dress

    Looking like a postcard, feeling like a getaway. This floral satin maxi dress brings paradise to the party with a silky flow, vacay-approved vibes, and a strappy open back that says “catch flights and feelings.”

    Fit & Features

    • Premium satin fabric
    • Large floral print
    • Sleeveless V-neckline
    • Spaghetti straps
    • Open cross-back strappy design, tie closure
    • Fitted flowy silhouette, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000172

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropical Cutie Halter Cutout Wide-Leg Jumpsuit

    This tropical halter jumpsuit will transport you to a beautiful paradise! The sleeveless plunging halter neckline and cutout bodice are both trendy and flattering, while the wide-leg silhouette adds a touch of style to the stretchy smooth knit fabric. Complete the look in strappy sandals.

    Fit & Features

    • Tropical palm leaf print
    • Smooth knit fabric, moderate stretch
    • Plunging halter neckline with tie closure, partial open back
    • Cut out bodice
    • Hip-hugging fit
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2493

    Category Name: Vacation Looks

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Destination Paradise Tropical Slit Maxi Dress

    Make a statement in this tropical maxi dress on your next visit to paradise! This stunning strapless maxi dress features an alluring side cutout and flirty side slit that creates movement with every step.

    Fit & Features

    • Tropical print, smooth knit stretchy fabric
    • Strapless neckline
    • Side cutout with adjustable drawstring
    • High side slit
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000138

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylishly Glam Strappy Rhinestone Pearl Sandals

    Strappy and stylish, these sandals are designed with glam rhinestones and faux pearl trims that elevate every look.

    Fit & Features

    • Square toe
    • Strappy design
    • Rhinestone and faux pearl trims
    • Flat sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1281

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE, BLACK

    Available Size: 5.5, 9, 6, 6.5, 7, 7.5

    Product Badge:
    • Sale
  • Chic Muse Watercolor Wrap-Slit Midi Skirt

    Showcase your iconic style like the chic muse you are in this printed wrap-slit midi skirt! Crafted from a breezy woven fabric with a stretchy knit lining, it is detailed with a gorgeous watercolor print for a mesmerizing look. This skirt features delicate pleating, leading to the wrap-slit front design and a midi-length hem. Style with the matching crop top and espadrille wedges for a sunset dinner!

    Shop Matching Top: Chic Muse Watercolor Tie-Front Crop Top

    Fit & Features

    • Watercolor print
    • Woven fabric, stretchy knit lining
    • High-rise pleated waist
    • Back zipper and hook-eye closure
    • Front wrap-slit design
    • Midi-length
    • Runs true to size

    Style Number/Barcode: 06301-0186

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale