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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Cutest Charm Striped Crochet Maxi Skirt
Serving retro flirtiness and the cutest charm. This striped crochet maxi skirt hugs just right and was made for rooftop hangs, concert nights, and spontaneous photo dumps. Style with the matching crop top.
Shop Matching Top: Cutest Charm Striped Crochet Halter Top
Fit & Features
- Striped crochet knit fabric
- High-rise waist
- Maxi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06501-000123
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: NATURAL
Available Size: S, M, L
Product Badge:- Part of a Set
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Flirty Chic Cutout Maxi Dress
The kind of dress that makes every plan feel a little more chic. With its flowy silhouette, flirty cutout detail, and side pockets, this maxi dress was made for vacations, weekend plans, and showers.
Fit & Features
- Gauze cotton woven fabric, woven lining
- Sweetheart neckline, spaghetti straps
- Open tie-back design
- Cutout bodice
- Hidden side pockets
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000559
Category Name: Vacation Looks
Price: $46.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Hot Plans Halter Crop Top
Cute plans just found their top. This textured halter crop top ties at the neck with a sculpted fit that keeps things sleek and ready for sunny days, festivals, and vacations.
Fit & Features
- Textured fabric
- Halter neckline with tie straps
- Open back
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06005-000337
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: CHARTREUSE
Available Size: L
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Brown Sugar Breeze Cutout Maxi Dress
This strapless maxi dress brings the kind of effortless allure that looks good from beach strolls to walks back to the hotel. The smocked fit, soft cutout detail, and flowy skirt keep it stylish with a pair of sandals.
Fit & Features
- Gauze woven fabric
- Strapless sweetheart neckline
- Stretchy smocked bodice with cutout
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000602
Category Name: Vacation Looks
Price: $56.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, L
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Island Afterglow Knit Maxi Dress
Booked the trip and get to wear this maxi dress. This long sleeve maxi dress brings that getaway glow with its open back and side slit made for sunset dinners and cocktails.
Fit & Features
- Texture knit fabric, smooth knit lining
- Plunge V-neckline, hardware insert
- Long bell sleeves
- Cutout bodice, open back
- High side slit
- Form-hugging, maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000155
Category Name: Vacation Looks
Price: $22.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: S, M
Product Badge:- Sale
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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, S, M, L
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Pretty Plans Eyelet Mini Dress
Caught feelings for this one instantly. This eyelet dress feels light and playful, perfect for brunch dates, daytime plans, or wherever the mood takes you.
Fit & Features
- Eyelet knit fabric, smooth knit lining
- V-neckline
- Adjustable spaghetti straps
- Fitted bodice
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000471
Category Name: Vacation Looks
Price: $19.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: XXS, XS, S, M, L
Product Badge:- Sale
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Weekend Style Studded Slide Sandals
These slide sandals add just the right amount of edge with a studded design for an effortless look.
Fit & Features
- Square toe
- H-shaped band with studs
- Flat sole
- Cushioned insole
- Faux suede material
- Runs true to size
Style Number/Barcode: 07404-000046
Category Name: Vacation Looks
Price: $18.90
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Day Plans Eyelet Open Back Mini Dress
Made for sunlit tables, pretty plates, and plans that start early and linger. This A-line mini dress features eyelet lace detailing and an open back, perfect for showers, graduations, and every daytime soiree.
Fit & Features
- Eyelet lace cotton woven fabric, stretchy knit lining
- Scoop neckline with trim
- Adjustable spaghetti straps
- Open back, stretchy smocked panel, hidden zipper and hook-eye closure
- Voluminous A-line silhouette
- Eyelet lace trim mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001021
Category Name: Vacation Looks
Price: $20.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
Product Badge:- Sale
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Fresh Picked Eyelet Mini Dress
This dress deserves a weekend away and a cute photo dump. The smocked eyelet mini dress features an off-the-shoulder neckline with flirty ruffle trim and an easy fit that works from brunch plans to beach town strolls.
Fit & Features
- Eyelet woven fabric
- Ruffled, off-the-shoulder neckline
- Stretchy smocked bodycon silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001037
Category Name: Vacation Looks
Price: $22.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
Product Badge:- Sale
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Blush Rush Halter Skater Dress
Cute enough to cause a double-take. This open back skater dress brings a flirty and polished vibe with a plunging neckline, trendy side pockets, and a flattering skater silhouette perfect for pairing with heels.
Fit & Features
- Smooth ponte fabric, knit stretchy lining
- Plunge halter neckline with tie straps
- Open back, zipper and hook-eye closure
- Hidden side pockets
- Skater mini-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001030
Category Name: Vacation Looks
Price: $45.90
Availability: In Stock
Available Color: PINK
Available Size: XS, L
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Checked In Lace Crop Top
Booked, packed, and already thinking about the vacation photos. This lace top pairs a plunge neckline with a flirty open front for an effortlessly styled getaway look.
Shop Matching Bottoms: Checked In Lace Shorts
Fit & Features
- Lace-lined fabric
- Plunge halter neckline, tie straps
- Open front design, beaded accents
- Flowy crop-length hem
- Runs true to size
Style Number/Barcode: 06001-000683
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Elevated Thong Platform Wedge Sandals
The effortless height your outfits have been waiting for. These thong wedge sandals add a sleek lift with a minimal strap design that pairs perfectly with your everyday looks.
Fit & Features
- Wedge heel
- Almond toe
- Wide thong strap
- Cushioned insole
- Platform sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07406-000039
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: BLACK
Available Size: 5.5, 7, 10
Product Badge:- Best Seller
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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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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: $19.97 $35.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- Sale
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Day To Night Halter Neck Top
Last-minute plans, handled. This halter neck top hugs just right with a smooth knit feel and a subtle cutout that keeps things sultry with your favorite bottoms.
Fit & Features
- Smooth knit stretch fabric
- Square cutout halter high neckline
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000533
Category Name: Vacation Looks
Price: $11.97 $27.90
On Sale: Yes
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: L
Product Badge:- Sale
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Café Cutie Tie-Front Top
The top that makes a simple capris-and-top combo look instantly styled. Featuring romantic ruffle trim, a tie-front closure, and a cropped silhouette, this crop top was made for coffee dates, weekend markets, and spontaneous plans.
Fit & Features
- Smooth satin fabric
- Ruffled trim tie-front neckline
- Cap sleeves
- Fitted crop-length hem
- Runs true to size
Style Number/Barcode: 06003-000348
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
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Checked In Lace Shorts
Booked, packed, and already thinking about the vacation photos. These lace shorts pairs a form-hugging fit with a flirty low-rise waist for an effortlessly styled getaway look.
Shop Matching Top: Checked In Lace Crop Top
Fit & Features
- Lace-lined fabric
- Low-rise waist, hoop insert belt accent
- Form-hugging fit
- Cheeky bottom
- Runs true to size
Style Number/Barcode: 06503-000335
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
Product Badge:- Part of a Set
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Brunch Booked Linen-Blend Midi Dress
Polished plans start here. This linen-blend belted midi dress balances a tailored square neckline with a breezy A-line skirt and front slit for brunches, showers, and dressed-up daytime plans.
Fit & Features
- Linen-blend fabric
- Sleeveless square neckline, thin tank shoulder straps
- Hidden side zipper closure, stretchy smocked back
- Belted waist, circular buckle
- Midi-length hem, high front slit
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000718
Category Name: Vacation Looks
Price: $65.90
Availability: In Stock
Available Color: YELLOW
Available Size: S, M, L
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Postcard Pending Asymmetrical Chiffon Top
Vacation plans just found their plus one. This sheer chiffon top drapes effortlessly with an asymmetrical neckline, flowy dolman sleeve, and tie-back detail made for beach clubs and sunset dinners.
Fit & Features
- Sheer chiffon fabric
- Asymmetrical neckline
- Short dolman sleeves
- Draped silhouette with tie-back detail
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06003-000476
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: TEAL
Available Size: XS, S, M, L
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Dreamy Daze Butterfly Poncho Top
Light, floaty, and a little unpredictable—in the best way. This butterfly floral poncho top with an asymmetrical off shoulder fit drapes effortlessly for that styled allure.
Fit & Features
- Butterfly floral tie-dye print, sheer mesh fabric
- Asymmetrical off-shoulder neckline
- Flowy poncho-silhouette
- Crop-length fit
- Runs true to size
Style Number/Barcode: 06001-000596
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S
Product Badge:- Part of a Set
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Toast Worthy Tie-Back Skater Dress
Serving polished with a little extra flirt. This crepe skater dress hugs up top, flares just right, and lets the tie-back moment catch glances—perfect for bridal celebrations, graduations, and any dressy occasion!
Fit & Features
- Crepe fabric, smooth knit lining with stretch
- Plunge sweetheart neckline, padded bra cups
- Tank shoulder straps
- Back zipper and hook-eye closure, tie-waist design
- Drop waist seam
- Skater mini-length silhouette, godet paneling for flare
- Runs true to size
Style Number/Barcode: 05101-001040
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: WHITE
Available Size: XXS, XS, M, L
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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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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: L