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.

  • Edge of Allure Halter Maxi Dress

    This one was made for your bold streak. The sheer mesh, curve-hugging fit, and plunging halter neckline bring instant “all eyes on me” energy—no extra effort required.

    Fit & Features

    • Abstract print, mesh fabric, sewn-in knit lining
    • Plunge halter V-neckline, tie closure
    • Open back
    • Hardware cinch at waist
    • Curve-hugging, sheer maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000596

    Category Name: Vacation Looks

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Sunset Glow Abstract Print Tie-Front Top

    Soft, sheer, and made for golden hour. This abstract print mesh tie-front top brings that effortless sultry vibe—flowy, flirty, and perfectly bold.

    Shop Matching Bottoms: Sunset Glow Abstract Print Mesh Maxi Skirt

    Fit & Features

    • Sheer mesh fabric, lettuce edge hems, high stretch
    • Abstract print
    • V-neckline, tie-front design
    • Long fitted sleeves
    • Mid-length hem
    • Runs true to size

    Style Number/Barcode: 06202-000069

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sea You Soon Huggie Earrings Set

    A little coastal charm, right where you need it. This two-pair huggie set features statement seashell details that bring easy, beachy energy to any look—no sand required.

    Fit & Features

    • Two pairs of huggie hoop earrings
    • Seashell designs
    • Polished metal finish
    • Clasp closures

    Style Number/Barcode: 07001-000213

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Luxe Frame Sunglasses

    Step into the sunshine with these ultra-chic round sunglasses featuring gold metal frames and soft tinted lenses for that perfectly polished finish. Effortless, timeless, and made for main-character days.

    Fit & Features

    • Round metal frames with tinted lenses
    • Gold-tone detailing with logo accents
    • Polished finish
    • 100% UV protection

    Style Number/Barcode: 07008-000096

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Midnight Mischief Chain Maxi Dress

    Made to steal the spotlight, this dress is designed to stun with a strapless bandeau bodice with an O-ring center and cascading chain details that frame the waist, finishing with a curve-hugging maxi skirt and side slit for that perfect mix of edge and allure.

    Fit & Features

    • Sleek knit fabric, short knit stretch lining
    • Strapless sweetheart bandeau top, padded bra cups
    • Hoop insert
    • Detachable cascading chains
    • High side slit
    • Form-hugging fit, long-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000555

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Seaside Whisper Shell Charm Bikini Bottoms

    Make a splash in this dreamy triangle bikini top, featuring a soft flocked texture that gives effortless coastal-cool energy. Finished with a delicate shell charm at the center, it’s the prettiest little detail for your next sun-kissed moment. 

    Shop The Matching Top: Seaside Whisper Shell Charm Bikini Top
    Shop The Matching Cover Up:
    Seaside Whisper Cover Up Skirt

    Fit & Features

    • Flocked texture-lined fabric
    • Low-rise V-cut waist
    • Adjustable side ties
    • Cheeky bottom
    • Shell charm accent
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000017

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: L

    Product Badge:
    • Sale
  • Shore Thing Starfish Belly Chain

    Sun, sand, and sparkle. This dainty gold belly chain layers delicate strands with a tiny starfish charm for that subtle beach goddess vibe. Perfect over swimwear, with low-rise denim, or to add a touch of shimmer to your festival fit.

    Fit & Features

    • Dainty layered chain
    • Starfish charm
    • Lobster clasp closure

    Style Number/Barcode: 07002-000237

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shore Thing Starfish Arm Cuff

    Straight from the shore, styled for the city. This starfish cuff bracelet brings a touch of seaside charm with its textured metallic finish and open wrap design. Perfect for stacking or adding a little ocean energy to any look.

    Fit & Features

    • Polished metallic finish
    • Dual starfish ends with textured detailing
    • Open cuff design

    Style Number/Barcode: 07003-000166

    Category Name: Vacation Looks

    Price: $4.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Golden Bloom Flower Arm Cuff

    Bloom where the glam is. This floral cuff bracelet adds a feminine twist with polished petal details and an open design that’s equal parts delicate and statement. 

    Fit & Features

    • Polished metallic finish
    • Open cuff design with dual flower ends

    Style Number/Barcode: 07003-000165

    Category Name: Vacation Looks

    Price: $4.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everyday It Girl Rectangle Sunglasses

    These rectangle sunnies give serious quiet-luxury energy—clean lines, chic gold V accents, and a shape that goes with literally everything. They’re the pair you grab when you want to look put-together with zero effort.

    Fit & Features

    • Plastic rectangle frames
    • Tinted lenses
    • V-shaped accents

    Style Number/Barcode: 07008-000105

    Category Name: Vacation Looks

    Price: $4.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ocean Treasures Bikini Charms

    A little ocean magic for your swim looks—these gold sea life charms clip onto your bikini for an instant resort-worthy upgrade. Starfish, shells, and sandy-day sparkle make every beach moment feel a little more styled.

    Fit & Features

    • Three-piece charm set
    • Starfish, shell, and sand dollar motifs
    • Polished tone finish
    • Clasp attachments

    Style Number/Barcode: 07001-000225

    Category Name: Vacation Looks

    Price: $4.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Blossom Kiss Floral Pearl Earrings

    Flirty, feminine, and a little fancy. These flower earrings feature a delicate bloom with a faux pearl accent that adds just the right touch of soft glamour.

    Fit & Features

    • Floral design with faux pearl drop accent
    • Polished metal finish
    • Post-back closures

     

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

    Style Number/Barcode: 07001-000246

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Carefree Chic Strappy Sandals

    Your new “grab-and-go but still cute” sandals — strappy, sleek, and finished with metallic touches that make even the simplest outfit feel styled. Lightweight, comfy, and ready for any sunny day plans.

    Fit & Features

    • Glossy faux patent finish
    • Open round toe with toe-hardware strap
    • Multi-strap design
    • Adjustable ankle strap with buckle closure
    • Flat sole
    • Lightly padded footbed
    • Runs true to size

    Style Number/Barcode: 07404-000040

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ocean Glow Pearl Shell Earrings

    Channel full seaside siren energy with these dreamy shell drop earrings. Designed with textured gold-tone scallop shells and dainty faux pearl accents, they serve effortlessly “washed ashore but make it glam.”

    Fit & Features

    • Gold-tone textured shell design
    • Faux pearl embellishments
    • Drop-style earrings with cascading pearl dangles
    • Post-back closures 

     

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

    Style Number/Barcode: 07001-000231

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sand And Shine Triangle Bikini Top

    This triangle bikini top brings that effortless “I woke up glowing” energy with its sleek abstract metal trim. Easy to tie, easy to style, and perfect for that sun-kissed moment you know is happening the second you hit the beach. Shop the matching bottoms.

    Shop The Matching Bottoms: Sand And Shine Bikini Bottoms

    Fit & Features

    • Smooth stretch swim fabric
    • Triangle cups with removable padding
    • Abstract metal ring accent at the center front
    • Adjustable halter neck ties
    • Adjustable back tie closure
    • Runs true to size

    Style Number/Barcode: 07104-000013

    Category Name: Vacation Looks

    Price: $6.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Seaside Sweetheart Layered Necklace

    Channel pure coastal energy with this layered charm necklace made for sunny days, salty breezes, and that effortless beach-babe vibe. Three delicate chains are stacked to perfection, each featuring its own seaside icon—an iridescent shell, a dainty starfish, and a polished cowrie charm.

    Fit & Features

    • Layered chain necklace design
    • Gold-tone finish
    • Seashell, starfish, and cowrie charms
    • Lobster clasp closure

    Style Number/Barcode: 07002-000245

    Category Name: Vacation Looks

    Price: $3.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek Attitude Cutout Mini Tube Dress

    Sleek with a hint of attitude—this cutout tube dress leans into confidence without overdoing it. The smooth knit hugs effortlessly, while the cutout crisscross beading gives your waist that sculpted, stop-scrolling energy.

    Fit & Features

    • Smooth double-lined knit fabric, high stretch
    • Strapless straight-across neckline
    • Front waist cutout
    • Asymmetric strappy design, beaded stone accents
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000359

    Category Name: Vacation Looks

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Shoreline Siren Hoop Cutout Swimsuit

    This one-piece turns the beach into your runway with bold hoop cutouts and a plunge that knows exactly what it’s doing. The silhouette shapes, lifts, and flatters while giving you that effortless “I make swimwear look intentional” confidence.

    Fit & Features

    • One-piece swimsuit with O-ring cutout detailing
    • Deep plunge neckline with adjustable halter ties, removable padded bra cups
    • Open sides with high-cut leg
    • Stretch swim fabric with minimal coverage
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000016

    Category Name: Vacation Looks

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sand And Shine Bikini Bottoms

    These bikini bottoms brings that effortless “I woke up glowing” energy with its sleek high-hip silhouette. Easy to slip on, easy to style, and perfect for that sun-kissed moment you know is happening the second you hit the beach. Shop the matching top.

    Shop The Matching Top: Sand And Shine Triangle Bikini Top

    Fit & Features

    • High hip bikini bottom silhouette
    • Scrunch back seam for shaping
    • Smooth stretch swim fabrication
    • Minimal coverage for a bold finish
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000021

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Linked Up Luxe Oval Chain Belt

    When your outfit needs that little something, this belt steps in like the finishing touch you didn’t know you were missing. The textured oval chain-link design brings effortless polish to everything from low-rise moments to dressed-up nights.

    Fit & Features

    • Textured oval-link design
    • Lightweight metal construction
    • Adjustable chain with lobster clasp closure

    Style Number/Barcode: 07301-000348

    Category Name: Vacation Looks

    Price: $6.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lyla Lace A-Line Formal Dress

    Special Occasion

    Designed for the woman who knows how to captivate a room, the Lyla formal dress pairs romantic lace fabric with an effortless a-line floor-length silhouette. The halter neckline with a rosette, side waist cutouts, and front ruffle trim slit creates a sculpted, eye-catching moment that feels equal parts daring and refined.

    Fit & Features

    • Lace fabric lined with stretchy mesh and knit
    • Halter V-neckline with rosette trim
    • Open back with tie, lower zipper and hook-eye closure
    • Side waist cutouts
    • Front ruffled trim slit
    • A-line silhouette, floor-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, destination celebrations, formal galas, black-tie charity balls, luxe cocktail parties, anniversaries, fashion-forward soirees, holiday events, opera or theatre nights, birthday dinners, resort evenings

    Style Number/Barcode: 05002-000652

    Category Name: Vacation Looks

    Price: $19.97 $99.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Vibes Geometric Knit Halter Mini Dress

    Meet the mini dress that knows how to make an entrance without trying too hard. The geometric knit hugs just right, giving you that effortless, sculpted look for beach nights, rooftop drinks, and the best vacay vibes.

    Fit & Features

    • Sheer embroidered knit fabric, knit lining, high stretch
    • Abstract geometric pattern, metallic woven threading
    • Sleeveless V-neckline
    • Tie-back halter straps, partially open back
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000377

    Category Name: Vacation Looks

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coastal Crush Cutout Crochet Maxi Dress

    A dress that does the flirting for you. The cutout crochet shows just enough, while the shell and sequin details add that subtle shimmer that catches light—and attention—without trying. This is your out-all-day, glow-all-night kind of maxi dress.

    Fit & Features

    • Sheer crochet knit fabric, mini-length knit lining, moderate stretch
    • Sleeveless ruched knit top, no-slip strip, wired V-neckline
    • Tie-back halter spaghetti straps, eyelet trim, shell and sequin embellishments
    • Partially open back
    • Maxi-length hem, high-cut side slit
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000360

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Mood Lace-Up Velvet Stiletto Heels

    The kind of heels that flirt without trying. Made with plush velvet with dainty lace-up straps, they bring that subtle drama every outfit deserves—perfect for date nights, rooftop drinks, or when you just feel like turning heads.

    Fit & Features

    • Stiletto heel
    • Open square-shaped toe
    • Cutout toe strap design, thin metal accent
    • Thin lace-up strappy design, tie closure
    • Velvet material
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-000453

    Category Name: Vacation Looks

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free