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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Island Flirt Floral Crop Top
Serving vacation plans without the plane ticket. This tropical floral crop top features a draped cowl halter neckline and an open tie back that keeps things breezy and just a little extra.
Fit & Features
- Tropical floral print, mesh fabric, sewn-in knit lining
- Cowl halter neckline, tie straps
- Open tie back
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06001-000558
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
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Lowkey Bold Strapless Ruffle Hem Mini Dress
Not here to blend in—this one hugs, shapes, and makes an impression without trying. The strapless bodycon mini dress with a ruffle hem and sheer waist detail brings texture and dimension that feels just as good as it looks.
Fit & Features
- Textured knit fabric with partial knit lining, moderate stretch
- Strapless straight-across neckline
- Sheer waist insert
- Mini-length tiered ruffled hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000305
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Hayden Floral Satin A-Line Formal Dress
Special Occasion
A study in effortless elegance, the Hayden floral satin A-line gown is made for the kind of entrance that lingers. Designed with a softly ruched bodice and fluid skirt, it moves with you—polished, poised, and undeniably captivating.
Fit & Features
- Floral pattern, satin fabric
- Sweetheart strapless neckline
- Tie-back detail
- High front slit
- A-line floor-length silhouette
- Runs true to size
Where to Wear:
Prom, graduations, bridal celebrations, galas, upscale birthday events, fancy brunches, vacations, formal milestone parties, anniversaries, fashion-forward soirees
Style Number/Barcode: 05002-001379
Category Name: Vacation Looks
Price: $99.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free
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Molly Floral Pleated A-Line Formal Dress
Special Occasion
The Molly floral chiffon A-line gown moves like a dream with every step. The sweetheart strapless neckline and softly pleated skirt create a romantic silhouette that feels effortlessly elevated for any special occasion.
Fit & Features
- Paisley floral print, chiffon fabric, stretchy knit lining
- Sweetheart neckline, padded bra cups
- Keyhole bust cutout with tie
- Mini lace-up back, open back, lower zipper and hook-eye closure
- Pleated A-line floor-length silhouette
- Runs true to size
Where to Wear:
Destination and outdoor weddings, vacations, resort dinners, honeymoons, birthday soirees, summer cocktail parties, bridal showers, fashion-forward events
Style Number/Barcode: 05002-001464
Category Name: Vacation Looks
Price: $129.90
Availability: In Stock
Available Color: WHITE, PRINT
Available Size: XS, S, M, L
Product Badge:- Ships Free
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Styled Chic Button Halter Neck Mini Dress
Serving sculpted and styled without trying too hard. This halter neck mini dress hugs your curves with a sleek ribbed feel and subtle button detail that keeps it chic from every angle.
Fit & Features
- Ribbed knit fabric, high stretch
- Sleeveless V-neckline
- Varied button accents
- Halter strap, partially open back
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000316
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
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Island Escape Cutout Halter Jumpsuit
Booked the vibe before the trip even starts. This tropical print jumpsuit brings the island muse with a beaded halter neckline and bold cutout that turns every step into a statement.
Fit & Features
- Tropical print, knit stretchy fabric
- Halter neckline with tie straps
- Front cutout design
- Wide-leg fit
- Runs true to size
Style Number/Barcode: 06502-000096
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
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Serving Sweet Lace Ruffle Skater Dress
Caught feelings… for this dress. The sweet lace ruffle skater dress hugs up top then flares into playful tiers, perfect for parties, date nights, or any plan that needs a little extra attention.
Fit & Features
- Sheer lace fabric with lining, moderate stretch
- Sleeveless sweetheart neckline
- Twist-front bust design, small keyhole cutout
- Adjustable spaghetti straps
- Tiered ruffled design
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05101-001098
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: YELLOW
Available Size: XXS, M, L
Product Badge:- Best Seller
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Sweet Style Polka Dot Mesh Romper With Scarf
Sweet with a little edge. This polka dot mesh romper with a scarf accent hugs in all the right places, then flares into soft ruffles that move with you from plans to after plans.
Fit & Features
- Polka dot mesh fabric with knit lining, high stretch
- Sleeveless straight-across neckline,
- Drop waist seam
- Tiered ruffled design
- Mini-length overlay, fitted A-line silhouette
- Hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06503-000303
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
Product Badge:- Best Seller
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Flirt In Motion Chiffon A-Line Mini Dress
This one just RSVP’d yes to every plan on your calendar. The flirty, flowy chiffon A-line mini dress brings that barely-there feel with a statement open back that keeps all eyes on you.
Fit & Features
- Sheer chiffon fabric with lining
- Sleeveless halter neckline
- Halter tie-back spaghetti straps
- Open back, lower zipper closure
- Mini-length asymmetric hem
- Flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-001132
Category Name: Vacation Looks
Price: $52.90
Availability: In Stock
Available Color: BLACK, BLUE
Available Size: XS, S, M, L, XXS
Product Badge:- Best Seller
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Make Plans Eyelet Ruffle Mini Dress
Last-minute plans just got a major upgrade. This eyelet ruffle mini dress hugs through the bodice with a flirty drop waist and tiered skirt that’s made for showing up and standing out.
Fit & Features
- Eyelet knit fabric with knit lining, high stretch
- Strapless straight-across neckline
- Fitted bodice, ruched detailing
- Drop waist seam
- Tiered ruffled design
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000715
Category Name: Vacation Looks
Price: $38.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
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Dressed For The Moment Halter Mini
This dress keeps it simple, but never forgettable. The textured fabric hugs just right while the halter neckline and open back add a confident allure, fitting perfectly into your suitcase for vacay!
Fit & Features
- Textured sweater knit fabric
- Halter V-neckline
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 06005-000329
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Sunday In Bloom Strapless Midi Dress
This midi dress feels like a soft yes to every pretty plan on your calendar. The delicate floral print, smocked bodice, and flowy silhouette make it perfect for vacations, brunch, or any sunny day plans.
Fit & Features
- Floral borderprint, cotton woven fabric, smooth woven lining
- Strapless smocked bodice with stretch
- Back zipper and hook-eye closure
- Flowy A-line silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000798
Category Name: Vacation Looks
Price: $72.90
Availability: In Stock
Available Color: BLUE, PINK
Available Size: S, M, L
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Escape The City Metallic Wedges
These metallic wedge sandals bring vacay energy with a glossy metallic finish and adjustable ankle strap—made for sunset dinners, beachside strolls, and weekend trips.
Fit & Features
- 4.5" wedge heel
- Almond toe
- Clear PVC toe strap
- Adjustable ankle strap with buckle closure
- Cushioned footbed
- Espadrille and metallic material
- Runs true to size
Style Number/Barcode: 07406-000052
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: GOLD
Available Size: 6, 6.5, 7.5, 8, 8.5, 9, 10
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Coastal Plans Espadrille Wedges
Your outfit just found its finishing touch. These espadrille wedges give you that effortless lift with an H-shaped band design and a sleek faux leather footbed that elevates your weekend or vacay lineup.
Fit & Features
- 4.5" wedge heel
- Square toe
- H-shaped band design
- Adjustable ankle strap with buckle closure
- Faux leather footbed
- Espadrille sole
- Runs true to size
Style Number/Barcode: 07406-000051
Category Name: Vacation Looks
Price: $35.90
Availability: In Stock
Available Color: BLACK, GOLD
Available Size: 6.5, 8, 8.5, 9, 10, 5.5, 6, 7, 7.5
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City Stroll Gingham Shorts
First stop coffee, next stop wherever the day takes you. These gingham shorts are fitted through the waist, with a smocked feel and a flirty finish that make them an easy pick for laid-back plans or styled-up moments.
Shop Matching Top: City Stroll Gingham Halter Crop Top
Fit & Features
- Lightweight woven fabrication
- Mid-rise waist
- Gingham pattern
- Ruffled hem
- Cheeky fit
- Runs true to size
Style Number/Barcode: 06303-000053
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: RED
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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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: $44.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Play Nice Ruffle Romper
Spark your inner flirt in this ruffle romper designed with an open back moment and draped side ruffle sashes that move with you from day to night.
Fit & Features
- Smooth knit stretch fabric, sewn-in panty lining
- Halter V-neckline, tie straps
- Open back
- Fitted bodice
- Layered tier ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 06503-000284
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Back For More Halter Mini Dress
All eyes on you always. This knit mini dress hugs your shape with side ruching and an open-back moment that keeps the focus on you.
Fit & Features
- Sweater knit fabric, moderate stretch
- High halter neckline with tie straps
- Open back, adjustable strap
- Side ruched seams
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000419
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: LAVENDER
Available Size: M, L
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Soft Focus Floral Halter Skater Mini Dress
Plans pending, outfit already decided. This halter mini dress cinches you in with soft ruching and flows into tiered ruffles that move with every step, perfect for brunch dates, park hangs, and last-minute plans.
Fit & Features
- Lined mesh and lace fabrication
- Sleeveless halter neckline with adjustable neck tie
- Ruched bodice, back zipper and hook-eye closure
- Floral pattern
- Tiered ruffled skater silhouette
- Mini length hem
- Runs true to size
Style Number/Barcode: 05101-001094
Category Name: Vacation Looks
Price: $54.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Flirt Mode Ruffle Sleeve Tie-Front Top
A little sweet, a little bold—this one knows exactly what it’s doing. The tie-front top hugs in all the right places with ruffle sleeve detail that keeps it playful from brunch plans to late dinners. Style with the matching mini skort.
Shop Matching Bottoms: Flirt Mode Ruffle Mini Skort
Fit & Features
- Sleek knit fabric, high stretch
- V-neckline
- Tie-front design
- Short ruffle sleeves
- Ultra-cropped hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06202-000107
Category Name: Vacation Looks
Price: $22.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Threaded Romance Tie-Front Duster
This sheer gauze maxi duster drapes effortlessly with delicate floral embroidery and dual tie-front details that elevate anything underneath in seconds.
Fit & Features
- Sheer gauze woven fabric
- Dual tie-front
- Sleeveless design
- Sheer embroidered mesh waist inserts
- Floral embroidery detailing
- Breezy long-length hemline
- Runs true to size
Style Number/Barcode: 06204-000133
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Late Dinner Plans Tube Maxi Dress
This is what you wear when the evening calls for something a little elevated. This tube maxi dress hugs through the bodice with a ruched finish, then falls into a soft shark hem that moves with every step.
Fit & Features
- Soft jersey knit fabric, stretchy lining
- Strapless tube neckline, non-slip grip lining
- Ruched fitted bodice
- Flowy curve-hugging silhouette
- Shark-cut maxi hem
- Runs true to size
Style Number/Barcode: 05102-000787
Category Name: Vacation Looks
Price: $52.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M
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Resort Days Slide Sandals
Straight to the vacation outfit rotation. These slide sandals keep things clean and elevated, perfect for beachside brunches, souvenir shopping, and everything in your daytime lineup.
Fit & Features
- Square toe
- H-shaped band
- Cushioned insole
- Flat sole
- Metallic/faux leather material
- Runs true to size
Style Number/Barcode: 07404-000053
Category Name: Vacation Looks
Price: $18.90
Availability: In Stock
Available Color: GOLD
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
Product Badge:- Best Seller
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Poolside Ready Starfish Strap Sandals
Booked, busy, and beach-bound—these are coming with you. Designed with a cushioned insole and starfish accent, these thong strap flat sandals keep every step cute from pool days to weekend escapes.
Fit & Features
- Almond toe
- Thong toe strap with starfish accent
- Luxe fit cushioned insole
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-000070
Category Name: Vacation Looks
Price: $22.90
Availability: In Stock
Available Color: BROWN
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
Product Badge:- Best Seller