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 Gossip Lace Top
Cute enough to change your whole outfit mood in under five minutes. This lace halter top mixes a plunging neckline with delicate sheer details that goes with every plan this summer.
Fit & Features
- Lace fabric, bust lining
- Plunge halter neck with tie straps
- Sheer lace fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000657
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: In Stock
Available Color: MINT, BROWN
Available Size: XS, S, M, L
Product Badge:- Sale
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Double Take Ponte Knit Mini Skort
Short, sharp, and just a little unexpected. This ponte knit mini skort keeps it polished up top and playful with dual side slits, plus hidden shorts so you’re covered no matter the plan.
Fit & Features
- Ponte knit fabric, moderate stretch
- High-rise waist
- Pleated detailing
- Mini-length overlay, dual side slits
- Fitted A-line silhouette
- Hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06503-000304
Category Name: Vacation Looks
Price: $27.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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Best In Show Strappy Crop Top
A little daring, a lot unforgettable. This strappy top features a plunging neckline, front cutout detail, and an open back design that makes every vacation or spontaneous night out feel a little more exciting.
Fit & Features
- Sleek knit double-lined stretchy fabric
- Plunge V-neckline, bead strap, keyhole cutout
- Spaghetti straps shapes the strappy open back detail
- Beaded accents
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000572
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Brunch RSVP Embroidered Halter Top
Soft glam just entered the group chat. This embroidered halter top brings a deep V-neckline, tie-back detail, and a cropped fit that’s made for patio plans, date nights, and every “where’d you get that” moment.
Fit & Features
- Smooth woven fabric with a lightly structured feel, knit lining
- Halter silhouette with tie-back neck closure
- Deep V-neckline, padded bust
- Embroidered bodice with floral design and sequin embellishment
- Open back
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-000643
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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One More Selfie Halter Top
A halter top that inspires multiple selfies. This crop top features a statement hardware wrap detail and an open back design that was made for dinner reservations, parties, and vacations.
Fit & Features
- Smooth knit fabric, high stretch
- Plunge halter neckline, tie straps
- Open back
- Front wrap detail with hardware insert
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000640
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Polka Dot Drama Lace Trim Top
Polka dots, but make them flirt back. This lace trim top brings a sculpted padded bust, stretchy seamless knit, and adjustable straps for an easy little outfit upgrade with a chic attitude.
Fit & Features
- Polka dot seamless knit fabric, high stretch
- Sleeveless sweetheart neckline
- Sculpted and padded bust, lace trim
- Adjustable spaghetti straps
- Mid-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 07109-000044
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
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Ember Floral A-Line Midi Formal Dress
Special Occasion
Softly romantic with a polished edge, the Ember floral print midi dress floats with every step, made for those RSVP moments where effortless elegance is the goal. The linen-like fabric, scallop square neckline, and lace-up open back bring a modern, feminine twist to a timeless A-line silhouette.
Fit & Features
- Floral print, linen-like woven fabric, knit lining
- Scallop square neckline, adjustable spaghetti straps
- Side zipper closure
- Scallop side cutouts
- Lace-up open back
- Pleated A-line midi silhouette
- Runs true to size
Where to Wear:
Bridal celebrations, engagement parties and photoshoots, birthday brunches, garden parties, afternoon tea, winery tastings, vacations, honeymoons, formal celebrations
Style Number/Barcode: 05001-000659
Category Name: Vacation Looks
Price: $19.97 $119.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sheer Drama Lace Tie-Front Vest
Serving sheer drama with a flirty twist. This cropped lace tie-front vest is your new fave for layering over anything—or nothing at all.
Fit & Features
- Sheer lace fabric
- Sleeveless
- Dual tie front closures
- Cropped length hem
- Delicate ruffle trims
- Runs true to size
Style Number/Barcode: 06202-000030
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Day Party Darling Eyelet Mini Dress
The kind of dress that gets complimented before you even sit down. With its eyelet fabric, plunge halter neck, open back, and floaty skater silhouette, this dress was made for bridal brunches, garden parties, and every sunny RSVP on your calendar.
Fit & Features
- Eyelet woven fabric, knit lining
- Plunge halter neck, tie straps
- Open back,
- Skater silhouette
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000945
Category Name: Vacation Looks
Price: $32.96 $54.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- Sale
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Fancy Seeing You Floral Mini Dress
This floral mini dress understood the assignment. The sweetheart neckline, flirty ruffle hem, and snatched fit make it the kind of dress that makes an impression at graduations, birthday brunches, or any dressed-up occasion.
Fit & Features
- Woven fabric, stretchy knit lining
- Strapless sweetheart neckline, non-slip grip lining
- Back zipper closure
- A-line mini silhouette
- Ruffle trim hem
- Runs true to size
Style Number/Barcode: 05101-001004
Category Name: Vacation Looks
Price: $19.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
Product Badge:- Sale
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Carolina Mermaid Slit Formal Dress
Special Occasion
The Carolina slinky mermaid gown skims every curve with effortless elegance. A sculptural shell hardware detail at the halter neckline and a thigh-high slit bring a modern, artful finish that feels equal parts polished and unforgettable.
Fit & Features
- Slinky knit fabric, smooth knit lining
- Halter neckline with floral hardware detail
- Padded bra cups
- Open back, lower zipper and hook-eye closure
- High side slit
- Mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Weddings, bridal celebrations, black tie galas, vacations, honeymoons, engagement parties, rehearsal dinners, big birthday events, cocktail parties, red-carpet occasions
Style Number/Barcode: 05002-001644
Category Name: Vacation Looks
Price: $99.90
Availability: In Stock
Available Color: WHITE, BLACK
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free
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Check In Chic Polka Dot Halter Corset
Easy yes, zero hesitation. This halter crop top brings a clean fit with just enough drama—perfect for spontaneous plans and outfits that don’t need a backup.
Shop Matching Skirt: Check In Chic Polka Dot Mini Skirt
Fit & Features
- Woven knit fabrication
- Plunging halter neckline
- Hook and eye front fasten closure
- Flexible boning
- Polka dot pattern
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-000400
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Check In Chic Polka Dot Mini Skirt
Easy yes, zero hesitation. This mini skirt brings a clean fit with just enough drama—perfect for spontaneous plans and outfits that don’t need a backup.
Shop Matching Top: Check In Chic Polka Dot Halter Corset
Fit & Features
- Woven knit fabrication
- Ruched mid-rise waist
- Polka dot pattern
- Ruffled high side slit
- Mini length hem
- Runs true to size
Style Number/Barcode: 06501-000111
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
Product Badge:- Part of a Set
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Flirty Look Eyelet Flutter Sleeve Skater Dress
Caught feelings for this one instantly—she’s light, flirty, and made for plans that turn into pics. This eyelet skater dress hugs up top, then flares just right for brunch, dates, and every RSVP.
Fit & Features
- Woven eyelet fabric with lining
- Sweetheart neckline, button-front closures
- Short ruffle flutter sleeves, can be worn off-the-shoulder
- Back zipper closure
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05101-001031
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Polished Mood Linen-Blend Mini Skort
Serving polished plans and chic vibes. This linen-blend skort brings tailored style and a mini-length overlay perfect for brunch reservations, vacation dinners, and weekend city strolls. Pair with the matching halter vest.
Shop Matching Top: Polished Mood Linen-Blend Halter Vest
Fit & Features
- Linen-blend woven fabric
- High-rise waist
- Hidden side zipper closure
- Mini-length front overlay
- Fitted shorts
- Runs true to size
Style Number/Barcode: 06303-000050
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Rosé Forecast Floral Poppy Mini Dress
Felt cute, will definitely post. With its floral poplin print and flirty skater silhouette, this mini dress was made for brunches, showers, and being the best dressed at the winery.
Fit & Features
- Floral poppy print, cotton-blend woven fabric, woven lining
- Square neckline, adjustable spaghetti straps
- Back zipper and hook-eye closure
- Skater silhouette
- Bonded mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001090
Category Name: Vacation Looks
Price: $12.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Flowy Chiffon Strapless Babydoll Dress
Made for spontaneous plans and extra mirror checks. This strapless chiffon babydoll dress brings the flirty vibes with flowy layers, a mini hem, and that effortlessly dressed-up look.
Fit & Features
- Sheer chiffon fabric with lining
- Strapless sweetheart neckline
- Hidden side zipper and hook-eye closure
- Flowy, tiered, ruffle design
- Mini-length hem
- Babydoll silhouette
- Runs true to size
Style Number/Barcode: 05102-000489
Category Name: Vacation Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Polished Mood Linen-Blend Halter Vest
Serving polished plans and chic vibes. This linen-blend halter vest brings tailored style and an open-back detail perfect for brunch reservations, vacation dinners, and weekend city strolls. Pair with the matching mini skort.
Shop Matching Bottoms: Polished Mood Linen-Blend Mini Skort
Fit & Features
- Linen-blend woven fabric
- Sleeveless V-neckline
- Tie-back halter straps, partially open back
- Button-down front
- Fitted mid-length hem
- Runs true to size
Style Number/Barcode: 06204-000137
Category Name: Vacation Looks
Price: $14.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Blue Skies And Late Nights Mini Dress
This is the dress that makes every summer plan feel a little more exciting. Featuring a breezy bandana-inspired print, open-back halter neckline, and flirty skater silhouette, it's made for vacation dinners, sunset strolls, and saying yes to plans that weren't on the calendar.
Fit & Features
- Paisley print, chiffon fabric, woven lining
- Halter neckline, spaghetti straps
- Open back
- Stretchy smocked waist panel
- Skater mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000641
Category Name: Vacation Looks
Price: $15.00
Availability: Out of Stock
Product Badge:- Ships Free
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Trendsetter Faux Leather Shoulder Bag
Proof that the purse can carry the outfit. This faux leather shoulder bag brings a structured shape, knotted strap detail, and trendy buckle made for brunch reservations, night-out moments, and plans that keep moving.
Fit & Features
- Washed faux leather material, smooth finish
- Rectangular-shaped silhouette
- Fold-over design, buckle strap, magnetic button closures
- Shoulder strap with knotted details
- Faux leather-lined interior, single pocket
Style Number/Barcode: 07203-000177
Category Name: Vacation Looks
Price: $27.90
Availability: In Stock
Available Color: TAN
Available Size: NS
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Francine Floral A-Line Midi Formal Dress
Special Occasion
The Francine midi dress blends a soft floral print with eyelet lace trim fabric for a look that feels both romantic and refined. The sweetheart underwire bust neckline, lace-up back design, and drop waist seam create a beautifully sculpted silhouette, while the A-line midi hem with lace trim brings effortless movement to every step.
Fit & Features
- Soft floral print, cotton-blend woven fabric with eyelet lace trim
- Smooth woven lining with lace edge trim
- Sweetheart tie-bust lace trim neckline, underwire bust
- Lace trim adjustable shoulder straps, hidden side pockets
- Flexible boning inserts in the bodice, side zipper and hook-eye closure
- Lace-up back design, drop waist seam, A-line midi-length silhouette
- Runs true to size
Where to Wear:
Outdoor weddings, bridal showers, engagements, charity luncheons, dressy brunches, garden parties, afternoon tea parties, vacations, honeymoons, milestone occasions, summer cocktail parties
Style Number/Barcode: 05001-000803
Category Name: Vacation Looks
Price: $129.90
Availability: In Stock
Available Color: WHITE, PRINT
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free
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Kissed In Polka Dot Mesh Mini Dress
A little playful, a little risky, and fully worth the attention. This polka dot mesh mini dress hugs in all the right places with a plunge halter neckline, open back, and layered ruffle hem that was made for stealing the scene.
Fit & Features
- Polka dot print, mesh fabric, knit lining
- Plunge halter neckline, tie straps
- Open back
- Side ruched seams, fitted bodice
- Layered ruffle mini hem
- Runs true to size
Style Number/Barcode: 05102-000709
Category Name: Vacation Looks
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Flare Polka Dot A-Line Mini Dress
Both flirty and impossible to ignore. This polka dot mini dress hugs in all the right places before flaring into an easy A-line fit that’s made for dinner dates, rooftop plans, and drinks with the girls.
Fit & Features
- Smooth knit fabric, high stretch
- Polka dot print
- Sleeveless deep V-neckline
- Adjustable spaghetti straps
- Mini-length hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000679
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Siren Vibes Shell-Trim Halter Mini Dress
Serving siren vibes. This shell-trim halter mini dress brings a plunging cowl neckline, an open tie-back design, and a ruched bodycon fit that knows exactly how to make an entrance.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Sleeveless plunging cowl neckline, bar strap detail
- Shell embellished trim
- Tie-back halter straps, open back, lower tie-back spaghetti straps
- Ruched detailing
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-000941
Category Name: Vacation Looks
Price: $24.97 $54.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
Product Badge:- Sale