Vacation Looks

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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.

  • Garden Bloom Flower Earrings

    A little color, a lot of charm. These enamel flower stud earrings feature soft blue-and-white petals with a gold-tone finish—perfect for adding a touch of playful polish to any outfit.

    Fit & Features

    • Polished finish
    • Enamel flower design with blue and white detail
    • Post back closures

     

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

    Style Number/Barcode: 07001-000204

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Bloom Floral Mesh Maxi Skirt

    A maxi skirt that feels like slipping into vacation mode without even trying. The soft floral print mesh hugs just right, giving you that effortless “I’m ready for whatever” confidence—day plans or date nights included.

    Shop Matching Top: Vacay Bloom Floral Mesh Halter Top

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Large floral print
    • High-rise waist
    • Ruching
    • High-cut side slit
    • Maxi-length hem, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-000102

    Category Name: Vacation Looks

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sea Treasure Five-Pack Ring Set

    Straight from the shore and made to stack. This five-pack sea life ring set brings coastal energy with faux pearl accents, starfish details, and seashell-inspired designs. The perfect finishing touch for your next beachy outfit—or destination celebration.

    Fit & Features

    • Five-pack ring set
    • Starfish, seashell, floral, and sculptural designs
    • Polished finish

    Style Number/Barcode: 07004-000079

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Trio Earring Pack

    Consider this your instant polish pack—the kind of trio that makes any outfit feel a little more thought-out without the effort. Lightweight, chic, and finished with a touch of shine, these earrings bring that easy everyday glow you’ll reach for again and again.

    Fit & Features

    • Three pack set
    • Multi-colored design
    • Square-shaped silhouette with gold trim
    • Omega closures

     

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

    Style Number/Barcode: 07001-000228

    Category Name: Vacation Looks

    Price: $6.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sky Shimmer Sequin Mini Skirt

    This sequin mini skirt brings that easy, ethereal shimmer your outfit’s been begging for. The sequin print catches the light just right, while the built-in shorts keep everything cute, confident, and fully dance-floor approved. Shop the matching top.

    Shop The Matching Top: Sky Shimmer Sequin Lace-Up Top

    Fit & Features

    • Sequin print fabrication with soft texture, sewn-knit lining
    • Mid-rise waist with fitted silhouette
    • Mini length hem
    • Hidden back zipper closure
    • Runs true to size

    Style Number/Barcode: 06401-000034

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: S, M, L

  • Untamed Glam Mesh Maxi Dress

    For nights when subtle just isn’t in your vocabulary, this mesh maxi dress delivers full-throttle confidence. The abstract animal print, plunging neckline, and hardware detail hit that perfect mix of daring and glam, while the bodycon fit keeps the silhouette sleek and unforgettable.

    Fit & Features

    • Abstract animal print, mesh fabric, short knit lining
    • Plunging neckline with hardware detail
    • Fitted long sleeves
    • Bodycon maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000391

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Aubrey Lace Halter Mermaid Formal Dress

    Special Occasion

    Designed to turn heads, the Aubrey formal dress pairs delicate leopard floral lace with a sculpted halter neckline and wired plunge bodice for a confident, sculpted fit. Finished with a sweeping mermaid silhouette and front sash detail, it’s made for moments that deserve to be remembered.

    Fit & Features

    • Leopard, floral print, lace fabric, stretch knit lining
    • Wired plunge halter neckline with tie closure
    • Padded bra cups
    • Low back, zipper and hook-eye closure
    • Front sash accent, ruched mermaid silhouette
    • Floor-length hem
    • Runs true to size

     

    Where to Wear:

    Destination weddings, birthday celebrations, fashion-forward events, anniversaries, date nights, glam parties

    Style Number/Barcode: 05002-000809

    Category Name: Vacation Looks

    Price: $19.97 $79.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Goddess Glow Leaf Arm Cuff

    Channel full ethereal goddess energy with this gold leaf arm cuff that wraps your arm in shimmering, nature-inspired detail. With its sculpted leaf tips and flexible wrap design, it adds an instant dreamy, boho-chic vibe to any look—dressy fits, vacations, nights out, you name it.

    Fit & Features

    • Gold-tone flexible wrap arm cuff
    • Sculpted leaf accents on each end with rhinestones

    Style Number/Barcode: 07003-000208

    Category Name: Vacation Looks

    Price: $6.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Golden Drift Beaded Statement Necklace

    Bring effortless, earthy elegance to your look with this sculpted beaded statement necklace. Its mix of organic-shaped beads, tonal accents, and subtle texture gives off that soft-luxe vibe—like vintage coastal meets modern cool girl.

    Fit & Features

    • Assorted resin beads with organic, irregular shaping
    • Round spacer beads and filigree-style accent beads
    • Lobster clasp closure with adjustable extender chain

    Style Number/Barcode: 07002-000351

    Category Name: Vacation Looks

    Price: $3.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charm Check Tortoise Cat Eye Sunglasses

    Serving instant trendy energy, these tortoise cat-eye sunnies come with tiny pearl charms that sway every time you turn your head—aka extra drama in the cutest way.

    Fit & Features

    • Tortoise cat-eye frame
    • Pearl charm detailing at the temples
    • Dark-tinted lenses

    Style Number/Barcode: 07008-000102

    Category Name: Vacation Looks

    Price: $4.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bold Blend Bracelet Set

    A chic collision of glossy acrylic and gleaming gold makes this cuff the easiest way to elevate your wrist stack. Clean, modern, and a little unexpected—it’s the kind of piece that pulls your whole look together without saying a word.

    Fit & Features:

    • Mixed acrylic and metal cuff design
    • Smooth sculpted silhouette
    • High-shine gold accent
    • Easy slip-on style

    Style Number/Barcode: 07003-000215

    Category Name: Vacation Looks

    Price: $15.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vibe Check Statement Stone Necklace Set

    This necklace set shows up the way you wish every accessory would—bold, layered, and ready to elevate anything you throw on. The mixed textures and statement stone add that effortlessly chic vibe.

    Fit & Features

    • Two-pack necklace set
    • Layered necklace design with mixed chain textures
    • Faceted natural-style stone pendant at center
    • Adjustable lobster clasp closures with extenders

    Style Number/Barcode: 07002-000355

    Category Name: Vacation Looks

    Price: $24.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wild Crush Hoop Halter Crop Top

    When you want to bring a little chaos—in the cute way—this halter crop top steps in with all the confidence of a bold-print moment. Light, flouncy, and ready for any night you decide to turn up the charm.

    Shop The Matching Skort: Wild Crush Ruffle Mini Skort

    Fit & Features

    • Sheer mesh fabrication with animal print
    • Strapless neckline with halter strap featuring dual gold-tone O-ring hardware
    • Ruched bodice creating a fitted silhouette
    • Cropped hemline
    • Runs true to size

    Style Number/Barcode: 06001-000379

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bloom Boldly Flower Drop Earrings

    These cascading flower drop earrings bring that soft-glam drama your outfit’s been craving. Lightweight and eye-catching, they add just the perfect touch of bold.

    Fit & Features

    • Drop earrings with a cascading floral design
    • Acrylic petals with textured detailing
    • Gold-tone centers for subtle contrast
    • Lightweight construction for comfortable wear
    • Post-back post closure

     

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

    Style Number/Barcode: 07001-000232

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shoreline Shine Metal Shell Clutch

    This sculpted shell clutch is your instant glam upgrade — glossy, dimensional, and impossible to ignore. It brings that luxe, vacation-meets-night-out energy no matter what you’re wearing.

    Fit & Features

    • Hard case shell silhouette
    • Metallic high-shine finish
    • Short detachable chain top handle
    • Detachable crossbody chain strap
    • Spacious interior
    • Structured mini size

    Style Number/Barcode: 07203-000127

    Category Name: Vacation Looks

    Price: $13.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Mael Floral Rhinestone Mermaid Formal Dress

    Special Occasion

    Designed to mesmerize from every angle, the Mael gown drapes the body in a dreamy floral print that feels both romantic and striking. The rhinestone-kissed halter V-neckline and sultry open back create a fluid, sculpted silhouette that moves with unforgettable elegance.

    Fit & Features

    • Mesh-lined fabric with floral print and rhinestone embellishment
    • Halter V-neckline, spaghetti strap tie back closure, padded bra cups
    • Open back with flattering ruched detailing
    • Mermaid silhouette with floor-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, destination vacations, resort dinners, upscale date nights, engagement parties, art museum soiree, birthday celebrations, cocktail parties

    Style Number/Barcode: 05002-000750

    Category Name: Vacation Looks

    Price: $19.97 $84.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Street Sleek Sunglasses

    When you want that effortlessly cool vibe without even thinking about it, these everyday sunglasses do the work for you. Clean lines, a refined frame, and a just-right attitude make them the pair you grab on repeat.

    Fit & Features

    • Classic everyday silhouette
    • Smooth curved temples
    • Dark-tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000103

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty Intent Butterfly Side Sunglasses

    Delicate but definitely noticed. These sunglasses add a subtle glam touch that feels elevated, effortless, and just extra enough for everyday styling.

    Fit & Features

    • Rimless lens design
    • Butterfly side hardware detail
    • Rubber nose supports
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000108

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Signature Vibe Square Sunglasses

    These are the shades you wear when you want your vibe to speak first. The slim square silhouette adds that clean, modern edge you love for elevated 'fits and effortless daytime looks.

    Fit & Features

    • Rectangular metal frame
    • Sleek, slim silhouette
    • Dark-tinted lenses
    • Adjustable rubber nose pads for customized comfort
    • Lightweight construction

    Style Number/Barcode: 07008-000124

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Vibe Tie-Front Bandeau Bikini Top

    A little flirty, a little floaty—this tie-front bandeau bikini top brings soft glam with zero effort. The ruffled layer moves with you for that breezy, beach-dream vibe you’ll want in every sun-soaked moment.

    Shop Matching Bottoms: Flirty Vibe V-Cut Bikini Bottoms

    Fit & Features

    • Strapless bandeau neckline with flyaway ruffle layer
    • Center front tie detail for adjustable fit
    • Smooth stretch knit fabric
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 07104-000011

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Vibe V-Cut Bikini Bottoms

    Meet the bikini bottom that nails that effortless, flirty vibe without overthinking it. The sharp V-cut sculpts your shape and serves up that confident, beach-dream vibe you’ll want in every sun-soaked moment.

    Shop Matching Top: Flirty Vibe Tie-Front Bandeau Bikini Top

    Fit & Features

    • V-cut front waist
    • High-cut sides for a sleek, minimal look
    • Cheeky back coverage
    • Smooth stretch knit fabric
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000019

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Easy Days Raffia Buckle Slide Sandals

    Slip on and step out, plans optional. These raffia buckle slide sandals keep things polished yet stylish, perfect for a destination vacation or strolling a beachside town.

    Fit & Features

    • 1" Low block heel for comfortable lift
    • Open square toe
    • Single wide strap across the vamp
    • Decorative buckle detail
    • Slip-on mule silhouette
    • Raffia-textured upper
    • Runs true to size

    Style Number/Barcode: 07404-000043

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Mix It Up Three-Pack Hoop Earrings

    Options are the vibe. This hoop earring trio gives you three distinct looks to rotate, stack, or style solo depending on the mood you’re in.

    Fit & Features

    • Polished metal and resin construction
    • Classic hoop silhouettes in varied textures
    • Three pair set for versatile styling
    • Post back closures

     

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

    Style Number/Barcode: 07001-000243

    Category Name: Vacation Looks

    Price: $13.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Layton Mesh One Shoulder Mermaid Formal Dress

    Special Occasion

    Striking yet refined, the Layton mesh mermaid gown is designed for entrances that feel confident and considered. A one-shoulder neckline with hardware inset meets a sculpting side cutout, while the sheer floor-length hem adds fluid movement with a modern edge.

    Fit & Features

    • Mesh fabric, partial knit lining, sheer finish
    • One-shoulder neckline with hardware inset detail
    • Side cutout accented with coordinating hardware
    • Sheer mermaid floor-length hem
    • Runs true to size

     

    Where to Wear:

    Black-tie weddings, formal galas, red-carpet events, award nights, upscale destination weddings and receptions, luxury rooftop hotel soirees, city formal events, elegant evenings

    Style Number/Barcode: 05002-001694

    Category Name: Vacation Looks

    Price: $69.90

    Availability: In Stock

    Available Color: WHITE, BLACK, BROWN

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

    Product Badge:
    • Best Seller