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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Effortless Flirt Babydoll Mini Dress
Floaty, flirty, and effortless in the best way. This babydoll mini dress brings that easy, throw-on-and-go feel with a breezy fit that moves with you from daytime plans to last-minute outings.
Fit & Features
- Cotton-blend fabric with lining
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Partially smocked back
- Mini-length asymmetric hem, subtle distressed detailing
- Flowy babydoll silhouette
- Runs true to size
Style Number/Barcode: 05102-000485
Category Name: Vacation Looks
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Polished Mischief Halter Top
This halter keyhole top hugs in all the right places with a sleek, sculpted fit that pairs effortlessly with shorts or skirts for concerts or weekend looks.
Fit & Features
- Woven fabric, minimal stretch
- High neckline with keyhole cutout and tie-front detail
- Front hook-and-eye fasteners
- Partial open back design
- Mid-length fitted hem
- Runs true to size
Style Number/Barcode: 06003-000368
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Everyday Elevated Lace Capri Pants
The capris that quietly make the outfit. These capri pants hug just right with a lace trim detail that adds a little something extra whether you’re dressing them up or down.
Fit & Features
- Smooth knit fabric
- High-rise lace trim waist
- Form-hugging fit
- Knee-length hem
- Runs true to size
Style Number/Barcode: 06502-000106
Category Name: Vacation Looks
Price: $28.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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On The List Side Slit Maxi Skirt
This is your new favorite maxi skirt for vacations or weekend fun! Designed with a sleek, body-hugging fit and a high side slit, it keeps things minimal but still turns heads.
Fit & Features
- Lined knit fabric, high stretch
- High-rise waist
- High front slit
- Form-hugging
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06501-000152
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: WHITE
Available Size: S
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Cute Plans Wrap-Front Mini Skort
Cute plans just found their outfit. This mini skort pairs a flattering wrap-front design with fitted shorts, making it an easy pick for brunch dates, rooftop drinks, and every RSVP in between. Style with the matching tie-front top.
Shop Matching Top: Cute Plans Puff Sleeve Tie-Front Top
Fit & Features
- Linen-blend woven fabric
- High-rise waist
- Wrap-front design with mini-length overlay, tie waist detail
- Fitted shorts
- Dual back pockets
- Runs true to size
Style Number/Barcode: 06303-000063
Category Name: Vacation Looks
Price: $11.97 $29.90
On Sale: Yes
Availability: In Stock
Available Color: RED
Available Size: S, M, L
Product Badge:- Sale
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Caught Looking Rectangular Sunglasses
A little mysterious, a little unbothered. These rectangular sunglasses are the kind you throw on when the outfit already ate, and you just need the finishing touch for coffee runs, beach days, or avoiding eye contact with your ex.
Fit & Features
- Lightweight acetate frame
- Slim rectangular silhouette
- Tinted lenses
- Metal hinge detail at temples
Style Number/Barcode: 07008-000224
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
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Text Me Tomorrow Cat Eye Sunglasses
Equal parts polished and a little hard to read. These cat eye sunglasses are the finishing touch your outfit needed for rooftop dinners, coffee runs, and pretending you’re not checking who viewed your story.
Fit & Features
- Lightweight metal frame
- Soft cat eye silhouette
- Tinted lenses
- Thin arms with minimal hardware detail
Style Number/Barcode: 07008-000239
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
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No Effort Needed Aviator Sunglasses
These square aviator sunglasses sharpen any look with sleek metal frames and tinted lenses that instantly pull everything together.
Fit & Features
- Square aviator silhouette
- Tinted lenses
- Rubber nose supports
- 100% UV protection
- Polished finish
Style Number/Barcode: 07008-000237
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: SILVER
Available Size: NS
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Invite Ready Ruffle Satin A-Line Mini Dress
Cue the invite—you already know what you’re wearing. This ruffled satin A-line mini dress brings that floaty, flirty feel with just enough structure to keep it polished from brunch to wherever the day takes you.
Fit & Features
- Textured woven satin fabric
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps
- Back zipper closure
- Front cascading ruffled design
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-001384
Category Name: Vacation Looks
Price: $44.00 $62.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
Product Badge:- Sale
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Too Busy Booking Flights Aviator Sunglasses
Airport fit approved and iced latte ready. These oversized aviator sunglasses bring that cool without trying vibe, with a lightweight metal frame that works for beach days, errands, and every candid in between.
Fit & Features
- Lightweight metal frame
- Oversized aviator silhouette
- Tinted lenses
- Adjustable nose pads
Style Number/Barcode: 07008-000234
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: SILVER
Available Size: NS
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Sweet Escape Abstract Floral Ruffle Skort
This skort was made for sunny-day plans and spontaneous photo ops. The layered ruffle design adds dreamy movement, while the mini skort silhouette keeps it effortlessly cute from brunch with the girls to getaway adventures.
Shop Matching Top: Sweet Escape Abstract Floral Halter Top
Fit & Features
- Lightweight mesh fabrication
- Low-rise waist
- Abstract floral pattern
- Tiered ruffle silhouette
- Hidden cheeky shorts
- Runs true to size
Style Number/Barcode: 06503-000341
Category Name: Vacation Looks
Price: $34.90
Availability: Out of Stock
Product Badge:- Ships Free
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Off Duty Drama Aviator Sunglasses
Big shades, iced coffee in hand, zero explanations needed. These aviator sunglasses bring that low effort chic vibes with oversized lenses and sleek metal details that instantly pull the whole look together.
Fit & Features
- Lightweight mixed material frame
- Oversized aviator silhouette
- Tinted lenses
- Contrast bridge detail with metal accents
Style Number/Barcode: 07008-000235
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
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Dreamy Vibe Floral Print Woven Midi Dress
A dress that makes even last-minute plans feel a little more curated. This floral print woven midi dress brings that effortlessly dreamy vibe with a flattering V-neckline, floaty A-line fit, and the kind of silhouette that works for brunch dates and weekend markets.
Fit & Features
- Woven fabric
- Dainty floral print
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Smocked back, zipper closure
- Midi-length ruffled hem, A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000820
Category Name: Vacation Looks
Price: $28.97 $64.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
Product Badge:- Sale
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City Break Linen Blend Vest
Tailored enough to look planned, easy enough to wear on repeat. This linen blend button up vest brings a clean, structured fit that's perfect for looking polished this season.
Fit & Features
- Linen-blend fabric, sewn-in woven lining
- Four-button up front closures
- Sleeveless vest silhouette
- Faux pockets
- Tailored seams
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06204-000179
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: NATURAL, WHITE
Available Size: L, S, M
Product Badge:- Sale
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Polka Dot Plans Halter Top
The print is playful, the fit is not here to play. This polka dot halter top brings a deep V-neckline, tie-back straps, and a curve-hugging stretch fit made for brunch detours, rooftop plans, and last-minute “actually, I’m going” texts.
Fit & Features
- Polka dot knit fabric, high stretch
- Sleeveless deep V-neckline
- Tie-back halter spaghetti straps, partially open back
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06002-000654
Category Name: Vacation Looks
Price: $22.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Daytime Vibe Floral Eyelet Strapless Midi Dress
Currently planning your next cute daytime moment. This floral eyelet strapless midi dress hugs up top with a smocked fit, then flows out for that easy, throw-on-and-go vibe—perfect for brunch, beach days, or last-minute plans.
Fit & Features
- Woven floral eyelet fabric
- Strapless straight-across neckline
- Fitted smocked bodice
- Midi-length flowy A-line silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05102-000498
Category Name: Vacation Looks
Price: $9.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cutest Flirt Flutter Sleeve Skater Dress
You'll be the cutest flirt in this floral eyelet skater dress featuring short flutter sleeves, a drop waist design, and a tiered A-line silhouette. Style with espadrille wedges for weekend brunch!
Fit & Features
- Floral eyelet woven fabric, woven lining
- V-neckline, small keyhole cutout below the bust
- Short flutter sleeves, adjustable straps
- Back zipper closure, tie-back design
- Drop waist design
- Tiered mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05101-000898
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: L
Product Badge:- Sale
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Sculpted Shine Ring Set
Sleek, sculpted, and impossible to miss. This four-piece gold ring set mixes bold statement shapes with minimalist shine—perfect for stacking or wearing solo when you want to flex subtle luxury.
Fit & Features
- Four-piece ring set
- Polished finish
- Mix of sculptural and smooth band designs
Style Number/Barcode: 07004-000080
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Play It Bold Drop Hoop Earrings
Statement hoops that do the talking. These drop hoop earrings bring that polished shine with a hint of edge—perfect for elevating your everyday lineup or finishing a last-minute outfit.
Fit & Features
- Drop hoop design
- Round metal stud
- Open metal and resin hoop
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000369
Category Name: Vacation Looks
Price: $9.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Soft Glam Floral Applique Mini Dress
Cute, but make it a little extra. This bodycon mini dress hugs just right with delicate floral applique details that feel made for dressy daytime plans and bridal soirees.
Fit & Features
- Smooth knit-lined stretchy fabric, floral applique
- Square neckline
- Adjustable spaghetti straps
- Side ruched seam
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001080
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: L
Product Badge:- Sale
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Flirty Polish Lace V-Neck Mini Dress
This lace skater dress features a soft, fitted bodice with a floaty skirt silhouette that feels made for bridal events, graduations, and every dressed-up occasion!
Fit & Features
- Lace fabric, lined
- V-neckline
- Adjustable spaghetti straps
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001134
Category Name: Vacation Looks
Price: $44.90
Availability: Out of Stock
Product Badge:- Ships Free
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Softly Subtle Leaf Chain Necklace
This delicate lariat necklace drapes just right with dainty leaf details that catch the light and adds the perfect complement to your look.
Fit & Features
- Layered delicate chain design
- Leaf charm accents
- Lariat silhouette
- Lobster clasp closure
Style Number/Barcode: 07002-000437
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Stack The Attitude Five-Pack Ring Set
More rings, more attitude—because one is never enough. This five-pack ring set mixes asymmetric designs so you can stack, layer, or wear solo depending on the mood.
Fit & Features
- Five-pack ring set
- Multiple asymmetric designs
Style Number/Barcode: 07004-000127
Category Name: Vacation Looks
Price: $15.90
Availability: Out of Stock
Product Badge:- Ships Free
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Next Layer Seamless V-Neck Bodysuit
The base layer that does the most. This seamless bodysuit smooths, sculpts, and offers a sleek silhouette made to be worn under everything or styled on its own.
Fit & Features
- Seamless knit stretchy fabric
- Bonded V-neckline
- Adjustable spaghetti straps
- Form-hugging smooth fit
- Thong bottom
- Dual snap-button closures
- Runs true to size
Style Number/Barcode: 07102-000058
Category Name: Vacation Looks
Price: $18.90
Availability: In Stock
Available Color: WHITE
Available Size: L