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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City Darling Lace Skater Mini Dress
Last-minute invite? Already handled. This lace tube skater dress hugs through the bodice with a flirty flare skirt that’s made for graduations, bridal celebrations, and every dressy plan in between.
Fit & Features
- Lace fabric with lining
- Strapless tube neckline
- Fitted skater silhouette
- Flowy mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001171
Category Name: Vacation Looks
Price: $64.90
Availability: In Stock
Available Color: WHITE
Available Size: M, L
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Take The Lead Argentina Baby Tee
Plan your outfit accordingly for game day with this "Argentina" baby tee to look cute rooting for your fave team. This fitted top brings sporty charm with adjustable side drawstrings and varsity stripes that pair well with denim and sneakers.
Fit & Features
- Cotton-blend knit fabric, high stretch
- Contrast crew neck trim
- Varsity striped shoulder detail
- Short sleeves, contrast trim
- Front "Argentina" script and patch accents
- Adjustable side drawstrings, fitted cropped hem
- Runs true to size
Style Number/Barcode: 06002-000553
Category Name: Vacation Looks
Price: $17.00 $27.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
Product Badge:- Sale
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All Eyes On You Sequin Floral Top
Subtle? Not today. This sequin floral spaghetti strap top catches the light from every angle with a low back tie detail that keeps things barely there and unforgettable—perfect for birthdays, date nights, and any excuse to dress up.
Fit & Features
- Lightweight fabric with sequin floral embellishment
- V-neckline with spaghetti straps
- Open lace-up back with tie closure
- Cropped silhouette
- Runs true to size
Style Number/Barcode: 06003-000212
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: RED
Available Size: S, M, L
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A Bit Flirty Lace Halter Dress
This lace mini dress gives you that effortless twirl moment with a light, easy fit that feels made for bridal celebrations, birthdays, graduations, and every dressed-up moment.
Fit & Features
- Lace-lined fabric
- Halter neckline with tie straps
- A-line silhouette
- Layered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000950
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: IVORY
Available Size: XXS, XS, S, M, L
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Garden Party Glam Floral Clutch
The kind of bag that gets compliments before you've even said hello. Covered in sequin floral embroidery and finished with a sleek box silhouette, this clutch brings a romantic, dressed-up feel to weddings, showers, and every RSVP on your calendar.
Fit & Features
- Sequin-embellished flower designs
- Structured box clutch silhouette
- Polished hardware trim
- Detachable chain strap
- Spacious interior
Style Number/Barcode: 07204-000061
Category Name: Vacation Looks
Price: $28.90
Availability: In Stock
Available Color: MULTI
Available Size: NS
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Barefoot In Bloom Eyelet Midi Dress
Feels like the kind of dress you pack for a weekend you don’t want to end. This eyelet midi dress keeps things light and romantic with a flowy tiered skirt, delicate straps, and an open tie back for a stylish flair.
Fit & Features
- Eyelet cotton woven fabric, stretchy knit lining
- Square neckline
- Adjustable spaghetti straps
- Tie-back
- Flowy ruffled A-line silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-001089
Category Name: Vacation Looks
Price: $62.90
Availability: In Stock
Available Color: WHITE
Available Size: XXS, XS, S, M, L
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Studded Style Open Back Top
Your outfit just got sharper. This crop top brings a plunge cowl halter neckline, tie straps, allover studded embellished trim, and an open back that makes everyone look back.
Fit & Features
- Slinky knit stretchy fabric
- Plunge cowl halter neckline with tie straps
- Open back
- All-over studded trim
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000690
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Sweet Escape Eyelet Mini Dress
This one belongs at sunset dinners, rooftop pics, and every RSVP you almost skipped. The eyelet mini dress hugs just right through the bodice with an easy flared fit that keeps it cute and comfortable all night.
Fit & Features
- Lightweight eyelet fabrication, knit lining
- Off-the-shoulder neckline
- Draped cold shoulder accents
- Ruched bodice
- A-line silhouette
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-000691
Category Name: Vacation Looks
Price: $35.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Cute Plans Puff Sleeve Tie-Front Top
Cute plans just found their outfit. This tie-front top pairs a flattering fitted shape with playful puff sleeves, making it an easy pick for brunch dates, rooftop drinks, and every RSVP in between. Style with the matching mini skort.
Shop Matching Bottoms: Cute Plans Wrap-Front Mini Skort
Fit & Features
- Linen-blend cotton woven fabric, sewn-in knit lining
- Short puff sleeves
- Deep V-neckline
- Dual tie-front design
- Fitted mid-length hem
Style Number/Barcode: 06003-000366
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: RED
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Spotted On Your Calendar Polka Dot Romper
The RSVP came in, and so did the outfit. This polka dot romper pairs a draped mock neck, open back, and flouncy ruffle hem for a look that feels both polished and playful from brunch dates to birthday plans.
Fit & Features
- Polka dot mesh fabric with knit lining, high stretch
- Sleeveless mock neckline, tie-back straps
- Open back
- Ruched drop waist design
- Tiered ruffled overlay with mini-length hem, A-line fit
- Hidden built-in shorts
- Runs true to size
Style Number/Barcode: 06503-000352
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
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Polished Trouble Chiffon Halter Top
This top does all the flirting for you. The chiffon halter top features a draped sleeveless fit with an open back and tie details that instantly dress up every last-minute dinner invite.
Fit & Features
- Sheer chiffon fabric
- Sleeveless high halter neckline with tie strap
- Open back with tie strap
- Relaxed fit
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06003-000359
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
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Sweet Spot Polka Dot Capri Leggings
The vintage-inspired pair your closet has been waiting for. These polka dot capri leggings are finished with delicate lace trim for an effortlessly playful look that feels just as cute with kitten heels as it does with an oversized knit.
Fit & Features
- Polka dot print, knit fabric with stretch
- Lace trim mid-rise waist
- Form-hugging fit
- Capri-length silhouette
- Runs true to size
Style Number/Barcode: 06502-000123
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BLK/WHT-2
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Weekend Replay Off Shoulder Top
With an off-the-shoulder neckline, fitted ribbed knit, and nostalgic stripe pattern, this crop top is the perfect match for spontaneous weekend plans.
Fit & Features
- Striped pattern, rib knit fabric
- Off-the-shoulder neckline
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06002-000620
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
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Easy Escape Textured Stripe Halter Dress
Made for sunshine-filled plans and easy outfit decisions. This textured stripe dress features a smocked halter bodice and a softly flared skirt that creates beautiful movement with every step. Perfect for beach vacations, brunch dates, and warm-weather weekends that call for effortless style.
Fit & Features
- Texture striped knit fabric, partial knit lining
- Halter neckline with tie straps
- Open back
- Flowy silhouette with a ruffle hem
- Runs true to size
Style Number/Barcode: 05102-000753
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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RSVP Ruffle Chiffon Maxi Dress
Dress code understood. This chiffon maxi dress brings the pretty with an eyelash-trim V-neckline, bust-tie front, and tiered, ruffled silhouette made for bridal celebrations, fancy brunches, and dressy soirees.
Fit & Features
- Chiffon fabric, short woven lining
- Eyelash lace trim V-neckline, tie front bust
- Underbust and bodice eyelash trimming
- Adjustable spaghetti straps
- Hidden back zipper and hook-eye closure
- Tiered ruffled maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-001494
Category Name: Vacation Looks
Price: $64.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
Product Badge:- New Arrival
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Uptown Mood Chain Strap Shoulder Bag
Quiet luxury, but make it every day. This structured shoulder bag features a sleek chain strap and polished hardware—perfect for dressing up your daytime looks or finishing off your night-out lineup.
Fit & Features
- Half chain and faux leather shoulder strap with snap button closure
- Front strap with hardware insert
- Top zipper closure
- Spacious interior with zipper pocket
- Faux leather material
Style Number/Barcode: 07203-000155
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
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Butterfly Kisses Mesh Tie-Front Top
Floaty, flirty, and fully saved to the outfit inspo folder. This mesh butterfly print tie-front top hugs just right and pairs perfectly with the matching bottoms.
Shop Matching Bottoms: Butterfly Kisses Mesh Maxi Skirt
Fit & Features
- Butterfly print, mesh fabric, bust lining
- Long sleeves with flared cuffs
- Tie-front neckline
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06202-000088
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: TAUPE-2
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Street Stride Micro Suede Sneakers
Cool, comfy, and city-ready—these microfaux suede sneakers feature sleek faux leather side stripes and a rubber traction sole that’s made for moving. Perfect for errands, off-duty looks, or casual hangs.
Fit & Features
- Square toe
- Lace-up front placket
- Faux leather side-striped design
- Rubber traction bottom
- Micro faux suede material
- Runs true to size
Style Number/Barcode: 07405-000014
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: In Stock
Available Color: TAUPE
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 10
Product Badge:- Sale
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Rich Girl Routine Oval Sunglasses
The finishing touch that makes every outfit look intentional. With sleek metal frames, softly tinted lenses, and an easy-to-style silhouette, these sunglasses bring just the right amount of polish, whether you're dressing up denim or heading out for dinner plans.
Fit & Features
- Oval shaped silhouette
- Tinted lenses
- Rubber nose supports
- Sleek metal arms with plastic trim
- 100% UV protection
Style Number/Barcode: 07008-000166
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Such A Flirt Polka Dot Mesh Cowl Neck Top
Okay, but this top just RSVP’d yes for you. This polka dot mesh cowl neck top drapes perfectly with a plunging halter neckline and flirty open back, making it your go-to for party plans, birthday dinners, or that last-minute invite that has you walking in like you planned it all week.
Shop Matching Bottoms: Such A Flirt Polka Dot Mesh Mini Skort
Fit & Features
- Polka dot mesh fabric, high stretch
- Sleeveless plunging cowl neckline, bar strap detail
- Halter strap with dual button closure, open back
- Draped cropped hem
- Runs true to size
Style Number/Barcode: 06001-000471
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: BLACK/WHITE
Available Size: S, L
Product Badge:- Part of a Set
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Garden Kisses Flutter Sleeve Midi Dress
The kind of dress that makes even a casual brunch feel a little cinematic. This chiffon midi brings soft romance energy with flutter sleeves, delicate textured detailing, and an easy flowy fit.
Fit & Features
- Chiffon fabric, smooth woven lining
- V-neckline
- Flutter short sleeves
- Tie-back design
- Stretchy smocked underbust band
- Flowy A-line silhouette, midi-length hem
- Runs true to size
Style Number/Barcode: 05101-000980
Category Name: Vacation Looks
Price: $24.97 $54.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: XXS, XS, S, M, L
Product Badge:- Sale
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Sunny Plans Striped Crochet Strapless Mini Dress
Sunny plans, cute outfit, and you’re already out the door. This striped crochet mini dress hugs just right up top with a strapless fit and flares into an easy A-line that’s made for brunch, beach days, and last-minute invites.
Fit & Features
- Striped crochet knit fabric with knit lining, moderate stretch
- Strapless straight-across neckline, no-slip strip
- Mini-length hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000689
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Weekend Vibes Fringe-Trim Halter Top
Your weekend lineup just found its new favorite top. This fringe-trim halter top hugs in all the right places with textured knit fabric and a strappy open back that’s made for sunny days, concerts, and night-out plans.
Fit & Features
- Textured knit fabric
- Sleeveless high halter neckline, tie-back spaghetti straps
- Open back, dual tie-back strappy design
- Mid-length hanky hem, fringe trim
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-000293
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
Product Badge:- Best Seller
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Effortless Flirt Babydoll Mini Dress
Floaty, flirty, and effortless in the best way. This babydoll mini dress brings that easy, throw-on-and-go feel with a breezy fit that moves with you from daytime plans to last-minute outings.
Fit & Features
- Cotton-blend fabric with lining
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Partially smocked back
- Mini-length asymmetric hem, subtle distressed detailing
- Flowy babydoll silhouette
- Runs true to size
Style Number/Barcode: 05102-000485
Category Name: Vacation Looks
Price: $52.90
Availability: In Stock
Available Color: WHITE
Available Size: L
Product Badge:- Best Seller