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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Double Take Animal Print Mini Dress
The outfit equivalent of being impossible to forget. This animal print halter mini dress hugs in all the right places with a plunging cowl neckline, statement hardware, and a flirty ruffled hem made for plans that deserve a little extra attention.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Abstract animal print
- Sleeveless plunging cowl neckline, flower hardware accent
- Halter strap
- Lower back cutout, ruched detailing
- Mini-length ruffled hem, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-001050
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M
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Paradise Found Halter Mini Dress
Straight into the vacation outfit folder. This textured knit mini dress features playful side cutouts and cascading bead details that bring just the right amount of drama to beach cabanas, tropical dinners, and every photo-worthy plan.
Fit & Features
- Texture knit fabric, smooth kint lining
- High halter neckline, tie straps
- Open tie-back, lower zipper and hook-eye closure
- Side cutouts with beaded fringe trim
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000628
Category Name: Vacation Looks
Price: $52.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Brunch Booked Floral Mini Dress
Serving vacation mood before you've even packed a bag. This floral tube mini dress features a flattering A-line fit that feels effortless for brunch, parties, and every warm-weather plan that pops up.
Fit & Features
- Floral print, lined knit fabric
- Strapless tube neckline
- A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000581
Category Name: Vacation Looks
Price: $19.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: YELLOW
Available Size: XS
Product Badge:- Sale
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Chasing Sunlight Cutout Maxi Dress
For the girl who packs the outfit before she books the reservation. With dreamy florals, statement cutouts, and a leg-baring ruffle slit, this maxi dress was made for sunset dinners, oceanfront cocktails, and every vacation photo worth posting.
Fit & Features
- Floral pattern, mesh-lined fabric
- Sweetheart bra top, underbust detail, padded bra cups
- Bodice cutout
- Open tie-back design
- Center ruffled trim and slit accent
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05103-000917
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S
Product Badge:- Sale
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Ocean Air Mood Halter Maxi Dress
This is the kind of dress that makes every plan feel a little more exciting. The soft hue, textured fabric, and waist cutouts bring just the right amount of drama for beachside dinners, cocktails, and those nights that somehow turn into your favorite memories.
Fit & Features
- Texture knit fabric, knit lining
- Sweetheart halter neckline, tie strap, non-slip grip lining
- Hoop insert and cutout bodice and back
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000714
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
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Salt Air Breeze Crochet Maxi Skirt
This is the skirt that makes every vacation outfit look intentional. With its breezy crochet texture, leg-baring slit, and flowy fit, it's made for beachside strolls and cocktails in the cabana.
Shop The Matching Top: Salt Air Breeze Bandeau Tube Top
Fit & Features
- Texture crochet woven fabric
- Mid-rise waist with tassel ties
- Thigh-high slit
- Flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06301-000012
Category Name: Vacation Looks
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Extra Confident Cowl Neck Ruffle Romper
The group chat said “be casual,” but this cowl neck romper clearly had other plans. With a plunging neckline, playful ruffle details, and a flirty silhouette, it’s made for vacation dinners, rooftop cocktails, and every RSVP that calls for a little extra confidence.
Fit & Features
- Knit fabric, high stretch
- Sleeveless plunging cowl neckline
- Halter strap, open back, lower tie-back spaghetti straps
- Ruched drop waist
- Tiered ruffled mini-length overlay with A-line fit
- Hidden built-in shorts
- Runs true to size
Style Number/Barcode: 06503-000287
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: ORANGE
Available Size: S, L
Product Badge:- Best Seller
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Flash Warning Metallic Romper
All eyes stayed exactly where they were supposed to. This metallic knit romper brings the perfect mix of daring and glam with a plunge halter neckline, ruched sides, and a layered ruffle hem that moves with every step.
Fit & Features
- Metallic foil knit fabric, built-in shorts lining
- Plunge halter neck, tie straps
- Open back
- Ruched side seams
- Fitted drop waist seam
- Layered ruffle mini hem
- Runs true to size
Style Number/Barcode: 06503-000297
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: EMERALD
Available Size: XS, S, M, L
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Salt Air Breeze Bandeau Tube Top
This is the tube top that makes every vacation outfit look intentional. With its breezy crochet texture, tie-back design, and bandeau-style look, it's made for beachside strolls and cocktails in the cabana.
Shop The Matching Bottom: Salt Air Breeze Crochet Maxi Skirt
Fit & Features
- Texture crochet woven fabric, sewn-in knit lining
- Strapless sweetheart neckline
- Cinched bust
- Tie-back design
- Bandeau-silhouette
- Runs true to size
Style Number/Barcode: 06003-000323
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: In Stock
Available Color: NATURAL
Available Size: M, L
Product Badge:- Sale
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Untamed Charm Stone Beaded Maxi Dress
The kind of dress that changes the whole mood the second you walk in. With textured zebra burnout fabric, statement stone beaded straps, and a leg-baring front slit, this maxi dress was made for destination dinners, cocktail hour, and plans that call for a little extra confidence.
Fit & Features
- Burnout velvet zeubra striped pattern, mesh-lined fabric
- V-neckline
- Stone beaded spagehtti straps and back strap accent
- Open back design
- High front slit
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05002-001400
Category Name: Vacation Looks
Price: $69.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Weekend Repeat Striped Midi Dress
The kind of dress that makes outfit decisions feel way too easy. This striped halter midi dress hugs comfortably with a bodycon feel, making it the one you'll reach for on coffee dates, weekend plans, and vacations.
Fit & Features
- Striped knit fabric
- Halter neckline
- Bodycon fit
- Center back slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000389
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
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Brunch Bound Tie-Front Cropped Vest
Light, airy, and ready for wherever the day decides to go. This tie-front cropped vest brings an effortless, breezy feel with its lightweight woven fabric and ultra-cropped fit that's made for weekend brunch with your girls. Style with the matching maxi skirt.
Shop Matching Bottoms: Brunch Bound Ruffle High-Low Maxi Skirt
Fit & Features
- Lightweight woven fabric
- Sleeveless V-neckline
- Tie-front design
- Fitted, ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06204-000135
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Brunch Bound Ruffle High-Low Maxi Skirt
Light, airy, and ready for wherever the day decides to go. This ruffle maxi skirt brings an effortless, breezy feel with its lightweight woven fabric and high-low flowy fit that's made for weekend brunch with your girls. Style with the matching cropped vest.
Shop Matching Top: Brunch Bound Tie-Front Cropped Vest
Fit & Features
- Lightweight woven fabric, short knit lining
- High-rise waist
- Maxi-length hem with flowy high-low silhouette
- Ruffled design
- Runs true to size
Style Number/Barcode: 06301-000011
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: IVORY
Available Size: M, L
Product Badge:- Part of a Set
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Palm Breeze Beaded Maxi Skirt
The kind of skirt that makes every destination feel a little more glamorous. Designed with a curve-skimming fit, thigh-high slit, and beaded chain detail, this maxi skirt brings effortless drama to beach dinners, resorts, and every plan in between.
Shop The Matching Top: Palm Breeze Beaded Halter Top
Fit & Features
- Slinky knit double-lined stretchy fabric
- High-rise waist with detachable beaded swag chain
- Thigh-high slit
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 06501-000135
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Villa Nights Halter Crop Top
The kind of outfit that makes every entrance stunning. This halter crop top features a plunging neckline, open back, and beaded accents that effortlessly go from vacation dinners to special occasion plans.
Shop The Matching Skirt: Villa Nights High Slit Maxi Skirt
Fit & Features
- Slinky knit double-lined knit stretchy fabric
- Plunge halter neckline, beaded accents, tie straps
- Open back
- Fitted crop hem, side ruched seams
- Runs true to size
Style Number/Barcode: 06001-000688
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Charming Sweet Polka Dot Mini Dress
This polka dot mini dress was for the kind of getaway where your camera roll fills up before noon. With a draped halter neckline, and flirty sash details, this dress is ready for hotel brunches and strolling downtown.
Fit & Features
- Polka dot print, mesh fabric, smooth lining
- V-neckline
- Form-hugging fit
- Sash detailing
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000723
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
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Checking In Chiffon Mini Dress
This ruffle chiffon mini dress was made for resorts, celebrations, and every vacation photo that somehow becomes your favorite. Just add sandals and oversized sunnies.
Fit & Features
- Chiffon fabric, smooth lining
- Square neckline
- Adjustable spaghetti straps
- Ruffled A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001178
Category Name: Vacation Looks
Price: $54.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Villa Nights High Slit Maxi Skirt
The kind of outfit that makes every entrance stunning. This maxi skirt features a beaded cinch waist accent, thigh-high slit, and flowy fit that effortlessly goes from vacation dinners to special occasion plans.
Shop The Matching Top: Villa Nights Halter Crop Top
Fit & Features
- Slinky knit double-lined knit stretchy fabric
- High-rise waist with beaded cinch accent
- Thigh-high front slit
- Flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06501-000181
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Analia Chiffon Halter Cutout A-Line Dress
Special Occasion
Designed for the kind of entrance that lingers long after you leave, the Analia dress brings effortless drama to every formal occasion. This airy chiffon A-line dress features a striking halter neckline, plunging cutout detail, open back, and flowing skirt that moves beautifully from cocktail hour to the last dance.
Fit & Features
- Sheer chiffon fabric with full-length lining
- Sleeveless high halter neckline, plunging front cutout
- Tie-back halter spaghetti straps, open back, lower zipper with hook-eye closure
- Pleated waist
- Floor-length hem with high-cut front slit
- Flowy A-line silhouette
- Runs true to size
Where to Wear:
Vacation dinners, engagement parties, bridal showers, rehearsal dinners, black-tie galas, evening dinners, and rooftop parties.
Style Number/Barcode: 05002-001451
Category Name: Vacation Looks
Price: $74.90
Availability: In Stock
Available Color: RUST, IVORY
Available Size: XS, S, M, L
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Island Glow Metallic Mini Dress
Serving vacation plans, nights out, and spontaneous photo ops all in one look. This metallic halter mini dress brings the drama with a plunging cowl neckline, strappy open back, and tiered ruffle skirt that moves with every step.
Fit & Features
- Metallic sheen knit fabric, knit lining
- Cowl halter neckline, hardware insert, tie straps
- Open strappy back
- Form-hugging fit
- Layered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000904
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: MINT, PINK
Available Size: XS, S, M, L
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Take Me There Tube Top
Mentally somewhere with better weather. This tropical island graphic top brings vacation vibes to your everyday lineup with an easy strapless fit that pairs perfectly with denim, linen, and a mai tai.
Fit & Features
- Cotton-blend stretchy knit fabric
- Tube strapless neckline
- Airbrush tropical island graphic
- Fitted cro phem
- Runs true to size
Style Number/Barcode: 06002-000625
Category Name: Vacation Looks
Price: $19.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Party Starter Beaded Mini Skort
This skort understood the assignment and then went a little further. With beaded embroidery, swishy fringe detailing, and a flirty mini silhouette, it's made for concerts, bachelorettes, birthdays, and every plan that deserves a standout outfit.
Fit & Features
- Beaded embellished pattern, woven fabric
- Mid-rise waist
- Form-hugging silhouette
- Fringe trim mini-length hem
- Runs true to size
Style Number/Barcode: 06403-000154
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: ORANGE
Available Size: L
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Off The Record Shield Sunglasses
These shield sunglasses feature tinted frames and chain braided detail for a polished finish that makes even the simplest outfit look intentional.
Fit & Features
- Tinted frames
- Oversized shield silhouette
- 100% UV protection
- Metal arms with chain braided detail
Style Number/Barcode: 07008-000134
Category Name: Vacation Looks
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
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Dress Code Destination Midi Dress
RSVP secured, outfit handled. This floral mesh midi dress brings sweeping ruffles, an open back, and a halter neckline together for the kind of entrance that gets compliments before you even reach your table.
Fit & Features
- Floral print, mesh-lined fabric
- Plunge halter neckline, tie straps
- Open back
- Form-hugging fit
- Asymmetrical ruffled midi hem
- Runs true to size
Style Number/Barcode: 05102-000675
Category Name: Vacation Looks
Price: $24.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free