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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Postcard Pending Floral Satin Halter Mini Dress
RSVPs, brunch invites, weekend trips... this floral satin halter mini dress already said yes. The scarf-inspired neckline, open back, and silky fit make getting dressed effortless and chic.
Fit & Features
- Satin woven fabric, floral print with contrast border pattern
- Sleeveless halter neckline with knot detail, tie-back design, zipper and hook-eye closure
- Open back, lower tie-back straps
- Front hanky hem overlay
- Mini-length hem
- Fitted silhouette
- Runs true to size
Style Number/Barcode: 05101-001065
Category Name: Vacation Looks
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Glow Metallic Lace-Up Espadrille Wedges
The wedges your suitcase was hoping you’d pack first. These metallic lace-up espadrille wedges bring the extra touch to flowy dresses, denim cutoffs, and plans that definitely weren’t supposed to get this cute.
Fit & Features
- Espadrille wedge heel
- Open almond-shaped toe
- Metallic toe strap
- Metallic cross-front and lace-up strappy design, tie closure
- Metallic faux leather footbed
- Runs true to size
Style Number/Barcode: 07406-000069
Category Name: Vacation Looks
Price: $32.90
Availability: Out of Stock
Product Badge:- Ships Free
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No Text Back Beaded Crop Top
The kind of top that makes your group chat ask where it’s from immediately. This slinky knit crop top features bold front cutouts, beaded bar straps, and an open back that does all the flirting for you.
Fit & Features
- Slinky knit fabric, sewn-in mesh lining
- Plunge halter neckline
- Front cutout with beaded straps
- Open back
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000577
Category Name: Vacation Looks
Price: $14.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Sale
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Sunkissed Confidence Plunge Halter Top
Serving sunkissed confidence with zero effort required. This plunge halter top hugs in all the right places with a sleek, sculpted fit that was made for dinner plans, rooftop cocktails, and being the best dressed without even trying. Style with the matching maxi skirt.
Shop Matching Bottoms: Sunkissed Confidence Bodycon Maxi Skirt
Fit & Features
- Sleek knit fabric, high stretch
- Sleeveless plunging neckline, bar strap with beaded detailing
- Tie-back halter straps, partially open back
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000597
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: CHARTREUSE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Sunkissed Confidence Bodycon Maxi Skirt
Serving sunkissed confidence with zero effort required. This ruched maxi skirt hugs in all the right places with a sleek, sculpted fit that was made for dinner plans, rooftop cocktails, and being the best dressed without even trying. Style with the matching halter top.
Shop Matching Top: Sunkissed Confidence Plunge Halter Top
Fit & Features
- Sleek knit fabric, high stretch
- High-rise waist
- Ruched detailing
- High-cut side slit
- Maxi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06501-000151
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: CHARTREUSE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Breezy And Bold Tie-Front Top
Serving vacay looks and all the summer vibes. This tie-front top brings the perfect mix of breezy and bold with its deep V-neckline, flowy sleeves, and ultra-cropped fit made for rooftop drinks, dinner reservations, and every photo in between. Style with the matching wide-leg pants.
Shop Matching Bottoms: Breezy And Bold Wide-Leg Pants
Fit & Features
- Lightweight woven fabric
- Deep V-neckline
- Tie-front design
- Short flowy sleeves
- Fitted ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06204-000130
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: In Stock
Available Color: MUSTARD
Available Size: S, M, L
Product Badge:- Sale
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Pretty Vibes Floral Print Long Sleeve Tie-Front Top
Pretty from every angle, impossible to forget. This floral print tie-front top brings all the drama with flowy long sleeves, a lightweight fit, and mesh fabric that hugs in all the right places for nights when you feel like being a little extra. Pair with the matching mini skirt.
Shop Matching Bottoms: Pretty Vibes Floral Print Mini Skirt
Fit & Features
- Mesh fabric with high stretch
- Tropical floral and animal multi-print pattern
- Deep V-neckline
- Tie-front design
- Long flowy bell sleeves, billowy silhouette
- Fitted ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06202-000113
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: NATURAL
Available Size: S, M, L
Product Badge:- Part of a Set
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Pretty Vibes Floral Print Mini Skirt
Pretty from every angle, impossible to forget. This floral print mini skirt brings all the drama with a cascading ruffled accent, a lightweight fit, and mesh fabric that hugs in all the right places for nights when you feel like being a little extra. Pair with the matching tie-front top.
Shop Matching Top: Pretty Vibes Floral Print Long Sleeve Tie-Front Top
Fit & Features
- Mesh fabric with knit lining, high stretch
- Tropical floral and animal multi-print pattern
- High-rise waist
- Long side ruffled accent
- Mini-length hem
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 06501-000166
Category Name: Vacation Looks
Price: $12.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Daydream Detour Paisley Maxi Dress
Easy, floaty, and somehow always the prettiest thing in your closet. This floral paisley maxi dress features a flowy silhouette, lace trim details, and an open tie back that feels made for brunch, weekend markets, and sunny day plans.
Fit & Features
- Floral paisley print, woven fabric, short woven lining
- V-neckline, spaghetti straps
- Open tie-back
- Center front button-up closures
- Flowy maxi silhouette, sheer lace trim
- Runs true to size
Style Number/Barcode: 05102-000592
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Coastal Vibe Floral Embroidered Tie-Front Top
Cute enough to make the group chat ask where it’s from immediately. This floral embroidered linen-blend tie-front top brings the flirty details with a plunging neckline, floaty cropped fit, and barely-there straps made for vacation dinners, rooftop drinks, and last-minute plans that somehow turn into the best night.
Shop Matching Bottoms: Coastal Vibe Floral Embroidered Mini Skort
Fit & Features
- Linen-blend woven fabric
- Floral embroidered design
- Sleeveless plunging V-neckline
- Tie-front design
- Adjustable spaghetti straps, cross-back design
- Cropped flared hem
- Runs true to size
Style Number/Barcode: 06003-000322
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: In Stock
Available Color: NATURAL
Available Size: M, L
Product Badge:- Sale
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Postcard From Paradise Maxi Dress
Mentally already sipping something fruity by the water. This flowy maxi dress brings vacation dressing to life with a citrus postcard print, flirty front tie detail, and lace-up back that looks good from every angle.
Fit & Features
- Multi-printed design, woven fabric
- V-neckline with trim and tie bust
- Spaghetti straps
- Lace-up tassel back
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000572
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sea You There Pearl Charm Necklace
This layered charm necklace brings all the flirty little details with faux pearls, dainty chains, and starfish and seashell accents that make every outfit feel a little more vacation-coded.
Fit & Features
- Two-row layered design
- Dainty chains
- Faux pearl beading
- Starfish and seashell charms
- Lobster clasp closure with extender
Style Number/Barcode: 07002-000459
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Catch Me On Vacay Tropical Floral Midi Skirt
Booked the trip the second this top hit your cart. This tropical floral midi skirt has a sleek, flowy, A-line fit that’s ready for rooftop drinks, vacation pics, and every RSVP sitting in your camera roll. Style with the matching tube top.
Shop Matching Top: Catch Me On Vacay Tropical Floral Tube Top
Fit & Features
- Knit fabric with knit lining, high stretch
- Large tropical floral print
- High-rise waist, ruched detailing
- Midi-length hanky-style hem
- Flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 06501-000173
Category Name: Vacation Looks
Price: $34.90
Availability: Out of Stock
Product Badge:- Ships Free
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First Class Button Vest
Put together without even trying. This crew neck vest brings that polished but effortless vibe with a tailored button-up fit and slit design that makes getting dressed feel way too easy.
Shop Matching Bottoms: First Class High-Rise Shorts
Fit & Features
- Woven fabric
- Sleeveless crew neckline
- Front button-up design
- Center front slit
- Mid-length hem
- Runs true to size
Style Number/Barcode: 06204-000125
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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First Class High-Rise Shorts
Put together without even trying. These shorts bring that polished but effortless vibe with a tailored high-rise waist and curve-hugging design that makes getting dressed feel way too easy.
Shop Matching Top: First Class Button Vest
Fit & Features
- Woven fabric
- High-rise waist
- Extended button tab closure
- Curve-hugging fit
- Runs true to size
Style Number/Barcode: 06303-000045
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: NATURAL
Available Size: S, M, L
Product Badge:- Sale
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Catch Me On Vacay Tropical Floral Maxi Skirt
Booked the trip the second this skirt hit your cart. This tropical floral maxi skirt hugs in all the right places with a sleek fit that’s ready for rooftop drinks, vacation pics, and every RSVP sitting in your camera roll. Style with the matching tube top.
Shop Matching Top: Catch Me On Vacay Tropical Floral Tube Top
Fit & Features
- Knit fabric with lining, high stretch
- Large tropical floral print
- High-rise waist
- High-cut side slit
- Maxi-length hem
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 06501-000154
Category Name: Vacation Looks
Price: $15.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Catch Me On Vacay Tropical Floral Tube Top
Booked the trip the second this top hit your cart. This tropical floral tube top hugs in all the right places with a sleek strapless fit that’s ready for rooftop drinks, vacation pics, and every RSVP sitting in your camera roll. Style with the matching maxi skirt.
Shop Matching Bottoms: Catch Me On Vacay Tropical Floral Midi Skirt, Catch Me On Vacay Tropical Floral Maxi Skirt
Fit & Features
- Knit mesh fabric, high stretch, sewn-in knit lining
- Large tropical floral print
- Strapless straight-across neckline
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000616
Category Name: Vacation Looks
Price: $26.90
Availability: Out of Stock
Product Badge:- Ships Free
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Mood Board Stone Charm Necklace
Your jewelry stack just found its favorite plus one. This stone charm necklace mixes gemstone details with dainty heart and flower charms for the kind of layered look that makes even a basic tank feel fully styled.
Fit & Features
- Dainty chain-link design
- Stone beaded charms
- Gemstone charms
- Flower and heart charms
- Lobster clasp closure with extender
Style Number/Barcode: 07002-000453
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
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Beachy Charm Puka Shell Belly Chain
This puka shell belly chain brings the perfect mix of beachy charm and low-rise styling for bikinis, mini skirts, and every last-minute getaway 'fit.
Fit & Features
- Chain-link design
- Puka shell accents
- Lobster clasp closure with extender
- Adjustable fit
Style Number/Barcode: 07002-000458
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Vacation Flirting Halter Tunic Top
A little daring, a little vacation-coded, and fully worth the stare. This halter tunic top brings flowy movement, a dramatic open front, and an abstract print that makes even simple plans feel expensive.
Fit & Features
- Abstract print, sheer mesh fabric, bust lining
- Sweetheart halter neckline, tie straps, hoop insert
- Center front high slit opening
- Flowy long-length hem
- Runs true to size
Style Number/Barcode: 06001-000695
Category Name: Vacation Looks
Price: $15.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: MULTI
Available Size: S, M, L
Product Badge:- Sale
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Kristen Printed Rhinestone Formal Dress
Special Occasion
The Kristen mermaid gown brings together sculpted ruching, a dramatic plunge neckline, and shimmering rhinestone detailing for a look that feels unforgettable from every angle. The lace-up back and curve-skimming silhouette make it the perfect plus-one for every RSVP that calls for going all in.
Fit & Features
- Printed mesh-lined fabric, allover mini rhinestones
- Sculpted sweetheart neckline, padded bra cups
- Adjustable spaghetti straps
- Open lace-up back
- Mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Destination weddings, vacations, summer galas, cocktail soirees, formal celebrations, birthday dinners
Style Number/Barcode: 05002-001442
Category Name: Vacation Looks
Price: $29.97 $79.90
On Sale: Yes
Availability: In Stock
Available Color: RED
Available Size: XS, S, M, L, XL
Product Badge:- Sale
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Second Glance Beaded-Trim Halter Midi Dress
The kind of dress that gets a second glance before you even say a word. This beaded-trim halter midi dress hugs in all the right places with a textured knit feel, open lace-up sides, and an open back that makes every entrance look intentional.
Fit & Features
- Textured knit fabric, high stretch, knit lining
- Sleeveless V-neckline, beaded bar strap accent
- Tie-back halter spaghetti straps, beaded accents
- Open back, lower tie-back spaghetti straps, back zipper closure
- Open lace-up side design
- Midi-length hem, back slit detail, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000627
Category Name: Vacation Looks
Price: $10.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: XS
Product Badge:- Sale
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Espresso Martini Beaded Mini Dress
This beaded mesh mini dress brings a sculpted bodycon fit, flirty halter neckline, and shimmer details that catch every dim light, dance floor selfie, and “one more drink?” invite.
Fit & Features
- Beaded pattern, mesh fabric, lined
- Cowl halter neckline, tie straps
- Back zipper and hook-eye closure
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05103-000818
Category Name: Vacation Looks
Price: $59.90
Availability: In Stock
Available Color: BROWN
Available Size: L
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Table For Two Lace Maxi Dress
The kind of dress that keeps the compliments coming before you’ve even made it to dinner. This lace maxi dress hugs in all the right places with a curve-skimming fit and strappy open back that feels equal parts effortless and unforgettable.
Fit & Features
- Lace fabric, knit lining
- Sweetheart neckline
- Spaghetti straps
- Open strappy back
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-001131
Category Name: Vacation Looks
Price: $22.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Sale