Vacation Looks
Vacation dressing should be easy, stylish, and ready for wherever the day takes you. Start with mini sundresses and flirty rompers that work for both sightseeing and rooftop drinks at sunset. Add in flowy maxis, crochet cover-ups for poolside sunbathing, and sleek sunnies that instantly pull a look together. From cutoff denim shorts to swimwear with eye-catching details, these outfits keep your suitcase light and your style on point for every getaway moment.
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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.
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Floral Mood Mesh Maxi Skirt
Florals with a little edge. This mesh lace-up maxi skirt brings a sleek bodycon fit, lined stretch feel, and back slit detail made for plans that need a stronger outfit. Style with the matching tube top.
Shop Matching Top: Floral Mood Mesh Lace-Up Tube Top
Fit & Features
- Mesh fabric with full-length knit lining, high stretch
- Large floral print
- High-rise elasticized waist
- Back slit accent
- Maxi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06501-000133
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Polished Halter Bodycon Maxi Dress
A smooth, shine-kissed finish makes this one feel instantly dressed up. The curve-hugging shape, plunging neckline, and waist cutouts bring the drama for vacation dinners, cocktail parties, and every RSVP that needs a little extra.
Fit & Features
- Slinky knit fabric with stretch
- Halter neckline with plunging V front
- O-ring hardware at center waist
- Side and underbust cutout details
- Body-hugging maxi fit
- Runs true to size
Style Number/Barcode: 05102-000825
Category Name: Vacation Looks
Price: $19.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: CHARTREUSE
Available Size: XS, S, M, L
Product Badge:- Sale
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Sleek Hardware Cutout Halter Maxi Dress
Consider this your shortcut to a sharper going-out look. Metallic ring accents and angled front openings give this body-skimming dress a sculpted finish made for dressy occasions.
Fit & Features
- Lined smooth stretch knit fabric
- Halter tie neckline
- Front cutouts with metal hardware accents
- Body-skimming fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000807
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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All Eyes Here Crochet Mini Dress
This is the dress that gets the double-take. With a sculpting crochet-knit texture, side cutouts, and a lace-up back that steals the show, it's made for cocktails, birthday plans, and vacations.
Fit & Features
- Crochet fabric
- Strapless neckline
- Cutout design
- Lace-up back detail
- Bodycon mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000398
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Caught Daydreaming Butterfly Lace Top
Designed with intricate butterfly lace, subtle sequin details, and an open tie-back silhouette, this halter top is romantic and unforgettable. Pair it with your favorite bottoms and sandals.
Fit & Features
- Butterfly sequin-embellished fabric
- Halter V-neckline, tie straps
- Open tie-back detail
- Sheer fitted hem
- Runs true to size
Style Number/Barcode: 06003-000384
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: BROWN, TEAL
Available Size: XS, S, M, L
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Blooming With Plans Flower Earrings
These cascading flower earrings bring a playful touch of shine and movement that's ready for weddings, showers, and every RSVP on your calendar.
Fit & Features
- Polished metal finish
- Cascading flower design
- Sleek linear silhouette
- Fish hook with rubber stopper
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000409
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Art Of Accessorizing Statement Necklace
The kind of necklace that makes a simple outfit look styled. With its oversized pendant and mixed-material design, this statement necklace is perfect for vacations, weekend plans, and summer date nights!
Fit & Features
- Layered chain design
- Statement stone pendant
- Statement mixed metal and wood accent pendant
- Lobster clasp closure
Style Number/Barcode: 07002-000487
Category Name: Vacation Looks
Price: $16.90
Availability: Out of Stock
Product Badge:- Ships Free
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Beach Please Crochet Poncho
Vacation mode looks good on you. This crochet poncho adds an effortless layer of shimmer with a breezy open-knit design that's perfect for beach days, pool parties, and sunset dinners.
Fit & Features
- Sheer crochet fabric with shimmer
- Asymmetrical neckline
- Relaxed poncho silhouette
- Runs true to size
Style Number/Barcode: 06005-000391
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: WHITE
Available Size: XS/S, M/L
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Made To Move Beaded Fringe Tube Top
Made to move, not blend. This beaded fringe tube top brings a ruched sweetheart neckline, trendy beaded trim, and a fitted feel that takes your going-out lineup somewhere better.
Fit & Features
- Smooth knit fabric, high stretch
- Strapless sweetheart neckline
- Ruched bust, overlay with beaded fringe trim
- Mid-length angled hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000741
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Vacay Invite Rhinestone Tropical Floral Mini Dress
Vacation invite accepted. This rhinestone tropical floral mini dress brings the heat with a draped cowl neckline, tie-back halter straps, and a body-hugging fit made for plans worth dressing up for.
Fit & Features
- Lined smooth knit fabric, high stretch
- Large tropical floral print, rhinestone embellishments
- Sleeveless cowl neckline
- Tie-back halter straps
- Open back, lower tie-back spaghetti straps
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-001065
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
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Sunkissed Chic Cutout Crochet Maxi Dress
Resort plans just got a plot twist. This beaded crochet maxi dress serves sculpted curves with a sweetheart neckline, waist cutout, and chic bead details made for walking in and turning heads.
Fit & Features
- Crochet knit fabric with knit lining, moderate stretch
- Sleeveless sweetheart neckline, U-wired metal insert, beaded fringe design
- Padded bust, waist cutout
- Adjustable spaghetti straps
- Back zipper with hook-eye closure
- Maxi-length hem, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-001474
Category Name: Vacation Looks
Price: $35.96 $59.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: XS, S
Product Badge:- Sale
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Low Key Drama Open Back Plunge Dress
A dramatic neckline and an open back make this one an instant standout. This flowing dress pairs a plunging front with airy draped sleeves and a side-tie detail for an effortlessly elevated look with beautiful movement. Perfect for vacations, dinner dates, and special occasions where an unforgettable entrance is part of the plan.
Fit & Features
- Silky satin fabric, sewn-in woven lining
- Plunging V-neckline
- Open-back design, adjustable strap, lower zipper and hook-eye closure
- Draped long sleeves with side tie accents
- Curve-hugging mini-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001334
Category Name: Vacation Looks
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Paradise In Floral Midi Dress
The RSVP practically sends itself. This tropical floral midi dress features a breezy asymmetric hem and flattering halter neckline that was made for destination weddings, dinners, and vacation photos.
Fit & Features
- Abstract floral print, mesh-lined fabric
- Halter V-neckline
- Spaghetti straps
- Ruffled trim
- Flowy midi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000813
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: PINK-2
Available Size: XS
Product Badge:- Sale
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Amara Mesh Halter A-Line Formal Dress
Special Occasion
Easy, alluring, and made for warm-weather RSVPs, the Amara mesh A-line gown brings a breezy kind of drama to every step. A ruched halter bodice, front cutout, and double-slit skirt create movement that feels effortless, polished, and just a little unforgettable.
Fit & Features
- Mesh fabric, full coverage panty knit lining
- Halter neckline, tie straps, padded bra cups
- Open tie-back design
- Thigh-high front slit
- Flowy A-line floor-length silhouette
- Runs true to size
Where to Wear:
Destination weddings, beach weddings, honeymoons, vacations, resorts, birthday dinners, cocktail events, bachelorette weekends, sunset celebrations, yacht parties
Style Number/Barcode: 05002-001671
Category Name: Vacation Looks
Price: $29.97 $69.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Sale
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Bead Side Halter Maxi Dress
Minimal effort, major impact. This textured knit maxi dress brings a halter neckline, curve-skimming fit, and side cutouts with bead accents for dinner plans, vacations, and every invite that calls for something sleek.
Fit & Features
- Texture knit fabric, knit lining
- Halter neckline
- Back zipper and hook-eye closure
- Side cutouts with beaded straps
- High center back slit
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-001472
Category Name: Vacation Looks
Price: $33.96 $56.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN-2
Available Size: XS, S, M, L
Product Badge:- Sale
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Shore Thing Statement Earrings
These iridescent shell drop earrings pair luminous shine with textured metal accents for a look that feels equal parts beach treasure and polished statement.
Fit & Features
- Textured accent
- Iridescent shell drop silhouette
- Post-back closure
Earrings are final sale and may not be returned or exchanged
Style Number/Barcode: 07001-000405
Category Name: Vacation Looks
Price: $10.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Bloom Snap Flower Hair Clips
Your quick hair fix just got way cuter. This two-pack flower hair clip set brings a glossy petal design with claw clip closures for easy updos and half-up styles.
Fit & Features
- Two-pack hair clip set
- Tropical flower designs
- Claw clip closure
Style Number/Barcode: 07006-000139
Category Name: Vacation Looks
Price: $10.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: NS
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Treasure Box Two-Piece Ring Set
Why choose one statement ring when you can have a whole lineup? These colored statement gemstone stretch rings feature bold square and oval stones that instantly add personality, polish, and a little extra fun to every outfit.
Fit & Features
- Two-pack ring set
- Statement designs
- Colored gemstone insets
- Stretch fit bands
Style Number/Barcode: 07004-000144
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
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Talia Chevron Cutout Mermaid Dress
Special Occasion
Made for golden hour plans and every sunshine moment, the Talia mermaid dress brings resort-minded allure with an effortlessly sculpted finish. Designed in chevron knit with a sleek floor-length silhouette, front and side cutouts, and beaded strap details, it is your answer to sunset dinners, rooftop parties, and summer nights that call for a little extra.
Fit & Features
- Sheer knit fabric with an abstract chevron pattern, full-length knit lining, moderate stretch
- Sleeveless plunging V-neckline, padded bust
- O-ring cutout, waist cutouts, beaded strap design
- Adjustable spaghetti straps
- Open back, back strap with metal bar closure
- Floor-length mermaid silhouette
- Runs true to size
Where to Wear:
Vacations, resorts, brunch with the girls, sunset dinners, rooftop parties, and summer nights out.
Style Number/Barcode: 05002-001724
Category Name: Vacation Looks
Price: $69.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
- Sheer knit fabric with an abstract chevron pattern, full-length knit lining, moderate stretch
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Jet Set Rhinestone Tropical Floral Tube Top
Your outfit just booked the trip. This rhinestone tropical floral tube top brings a bright statement print, strapless neckline, and curve-hugging fit made for rooftop plans, resort dinners, and every photo that makes the group chat pause.
Fit & Features
- Knit fabric, high stretch
- Large tropical floral print, rhinestone embellishments
- Strapless straight-across neckline
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000712
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
Product Badge:- Sale
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Shade Check Cat Eye Sunglasses
Incognito, but make it intentional. These cat-eye sunglasses feature a sleek, angled frame that instantly sharpens errands, brunch looks, and coffee runs.
Fit & Features
- Plastic cat-eye sunglasses silhouette
- Tinted lenses
- Sleek angled frame
- 100% UV protection
Style Number/Barcode: 07008-000156
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Coast Calling Printed Maxi Duster
Vacation packing made easy. This sheer printed maxi duster features an easy tie-front waist, breezy short sleeves, and side slits that float with every step from the beach to sunset cocktails and everywhere in between.
Fit & Features
- Chevron printed design
- Airy woven fabric
- Relaxed short sleeves
- Open tie-front design
- High side slit
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 06204-000175
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: MULTI
Available Size: L
Product Badge:- Sale
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Wild Bloom Floral And Animal Print Romper
Print mix with no chill. This floral and animal print romper brings stretchy mesh, ruffled layers, and built-in shorts for when the plan is last-minute but the outfit needs receipts.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Floral and animal print pattern
- Sleeveless cowl neckline
- Tie-back halter straps, open back
- Drop waist, ruched detailing
- Tiered ruffled mini-length overlay, A-line fit, long ruffle accents
- Hidden built-in knit shorts
- Runs true to size
Style Number/Barcode: 06503-000325
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M
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Alison Striped Chiffon Formal Dress
Special Occasion
When the invite calls for something light, polished, and memorable, this one understands the assignment. The striped halter dress moves in airy chiffon with a front slit, open tie back, and A-line maxi shape. It gives your plans a statement finish while keeping the look effortless.
Fit & Features
- Striped chiffon fabric, knit lining, built-in knit shorts lining
- A-line maxi silhouette
- Halter neckline with open tie back, zipper and hook-eye closure
- Side cutouts and ruched waist
- Front thigh-high slit detail
- Runs true to size
Where to Wear:
Destination weddings, vacations, honeymoons, resort getaways, birthday dinners, date nights, brunch celebrations, cocktail parties, bachelorette trips, cruises
Style Number/Barcode: 05002-001688
Category Name: Vacation Looks
Price: $79.90
Availability: In Stock
Available Color: GREEN
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free