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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Hot Plans Tie Front Ruffle Sleeve Top
This one’s already booked for your next night out. This tie front ruffle sleeve top gives you that easy flirty fit with an adjustable front and a little movement in the sleeves for extra charm. Pair with the matching skirt for a look that turns heads.
Shop Matching Bottoms: Hot Plans High Waist Ruffle Midi Skirt
Fit & Features
- Soft stretch knit fabrication
- V-neckline with tie-front closure
- Short ruffled sleeves
- Cropped hem
- Runs true to size
Style Number/Barcode: 06202-000112
Category Name: Vacation Looks
Price: $22.90
Availability: In Stock
Available Color: NEON, PINK
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Vacation Glow Beaded Stiletto Heel Sandals
Serving sunset plans and cute outfit pics only. These beaded stiletto heel sandals bring all the playful detail with a barely-there fit that instantly elevates your going-out looks.
Fit & Features
- Faux leather material
- Strappy silhouette
- Adjustable ankle strap
- Beaded front strap detail
- Stiletto heel
- Runs true to size
Style Number/Barcode: 07401-000642
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: BROWN
Available Size: 8.5
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She's Bold Abstract Floral Midi Tube Dress
Fit & Features
- Sleek knit fabric, high stretch
- Abstract floral print
- Strapless straight-across neckline
- Ruched detailing
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000585
Category Name: Vacation Looks
Price: $19.97 $38.90
On Sale: Yes
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M
Product Badge:- Sale
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Pretty Little Crepe Skater Dress
Polished, but still feels effortless. This crepe skater dress brings a refined shape with a square neckline and lace-up back—perfect for brunches, showers, or any invite that calls for something a little elevated.
Fit & Features
- Crepe woven fabric, smooth woven and tulle linings
- Square neckline, lightly padded bra cups
- Adjustable shoulder straps
- Lace-up back, zipper and hook-eye closure
- Drop waist seam
- Skater mini-length silhouette
- Runs true to size
Style Number/Barcode: 05101-000889
Category Name: Vacation Looks
Price: $54.90
Availability: Out of Stock
Product Badge:- Ships Free
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In My Lace Era Mini Skort
Serving legs with a little extra detail—because basics just aren’t cutting it. This lace-trim mini skort hugs your shape while keeping things effortless from brunch plans to last-minute invites.
Fit & Features
- Ponte knit fabric with moderate stretch, sheer lace trim
- High-rise waist
- Mini-length overlay, form-hugging fit
- Hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06503-000300
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: OFF, WHITE
Available Size: XS, S, M, L
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Hot Plans High Waist Ruffle Midi Skirt
This one’s already booked for your next night out. This high-waisted ruffled skirt gives you an easy, flirty look with a flattering fit and feel throughout for extra charm. Pair with the matching tie-front top for a look that turns heads.
Shop Matching Top: Hot Plans Tie Front Ruffle Sleeve Top
Fit & Features
- Soft stretch knit fabrication
- High-rise waist with ruffle accent
- High side slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06501-000158
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: NEON, PINK
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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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: $10.97 $26.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, L
Product Badge:- Sale
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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, knit lining
- Sweetheart strapless neckline, padded bra cups
- Tie-back detail, lower zipper and hook-eye closure
- 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: $19.97 $99.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L, XL
Product Badge:- Sale
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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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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: $20.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: OLIVE
Available Size: S, L
Product Badge:- Sale
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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: Out of Stock
Product Badge:- Ships Free
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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
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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: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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: $17.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- Sale
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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: 07406-000049
Category Name: Vacation Looks
Price: $9.97 $35.90
On Sale: Yes
Availability: In Stock
Available Color: GOLD
Available Size: 10
Product Badge:- Sale
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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: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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: M, L
Product Badge:- Part of a Set
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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: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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
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
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Gallery Date Floral Midi Dress
This floral midi dress skims your shape with a cowl neckline and lace-up back, made for brunches, showers, and any dressy occasion you feel like showing up styled.
Fit & Features
- Artsy floral print, woven fabric, crepe lining
- Cowl neckline
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Lace-up back ties
- Side slit
- Curve-hugging, midi-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001410
Category Name: Vacation Looks
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simple Charm Gingham Mini Dress
Feels like a picnic invite just showed up. This gingham mini dress keeps it cute and easy with a collar, cap sleeves, and a button-down front that works from coffee shop hangs to casual plans.
Fit & Features
- Gingham pattern, cotton-blend woven fabric, woven lining
- Collar neckline
- Cap sleeves
- Front button-down closures
- Tie-back strap
- A-line mini silhouette
- Runs true to size
Style Number/Barcode: 05102-000598
Category Name: Vacation Looks
Price: $38.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Playful Plans Flamingo Earrings
Your outfit just found its personality. These flamingo statement earrings bring sparkle, feathers, and full-on fun to any occasion.
Fit & Features
- Teardrop rhinestone
- Rhinestone-embellished flamingos with faux feathers
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000380
Category Name: Vacation Looks
Price: $16.90
Availability: In Stock
Available Color: GOLD
Available Size: NS