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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Trendsetter Energy Beaded Trim Mini Skort
The kind of mini skort that makes accessorizing feel optional. With ruched detailing, beaded trim, and a trendy A-line fit, this one was made for spontaneous plans and getting complimented asap. Style with the matching halter top.
Shop Matching Top: Trendsetter Energy Beaded Trim Halter Top
Fit & Features
- Mesh fabric, high stretch
- High-rise waist
- Ruched design, adjustable drawstrings with beaded accents
- Asymmetric mini-length overlay, A-line silhouette
- Hidden built-in knit shorts
- Runs true to size
Style Number/Barcode: 06503-000255
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Trendsetter Energy Beaded Trim Halter Top
The kind of halter top that makes accessorizing feel optional. With ruched detailing, beaded trim, and a trendy fit, this one was made for spontaneous plans and getting complimented asap. Style with the matching mini skort.
Shop Matching Bottoms: Trendsetter Energy Beaded Trim Mini Skort
Fit & Features
- Mesh fabric with knit lining, high stretch
- Sleeveless deep V-neckline
- Tie-back halter straps
- Ruched design, adjustable drawstring with beaded accents
- Cropped hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000500
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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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
- 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: $46.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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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: In Stock
Available Color: GOLD
Available Size: 5, 5.5, 6, 6.5, 7, 7.5, 8.5
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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: $34.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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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: S, M, L
Product Badge:- Part of a Set
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Chic Moment Cat-Eye Sunglasses
With a chic cat-eye frame, sleek arms, and tinted lenses, these sunglasses were made for coffee runs, fab errands, and “just one pic” moments.
Fit & Features
- Square-shaped design
- Cat-eye frame
- Built-in nose pads
- Wide arms
- Tinted lenses
Style Number/Barcode: 07008-000128
Category Name: Vacation Looks
Price: $9.90
Availability: In Stock
Available Color: GREEN
Available Size: NS
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Sculpted Drama Flower Statement Linear Earrings
These earrings understood the assignment before you even picked the outfit. The sculpted flower statement design brings just enough drama to elevate a simple tank, silky slip dress, or last minute dinner look.
Fit & Features
- Statement linear design
- Sculpted metal silhouette
- Dual tropical flower accents
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000432
Category Name: Vacation Looks
Price: $16.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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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: $19.90
Availability: In Stock
Available Color: MUSTARD
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Breezy And Bold Wide-Leg Pants
Serving vacay looks and all the summer vibes. These wide-leg pants bring the perfect mix of breezy and bold with their pleated detailing and flowy silhouette made for rooftop drinks, dinner reservations, and every photo in between. Style with the matching tie-front top.
Shop Matching Top: Breezy And Bold Tie-Front Top
Fit & Features
- Lightweight woven fabric
- High-rise waist
- Front pockets
- Pleated detailing
- Flowy wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06402-000033
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: MUSTARD
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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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: XS, 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: $36.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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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: $54.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
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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: $29.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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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: $49.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
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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: In Stock
Available Color: GOLD
Available Size: NS
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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: In Stock
Available Color: FUCHSIA
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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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: $36.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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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: $36.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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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: $36.90
Availability: In Stock
Available Color: FUCHSIA
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Coastal Vibe Floral Embroidered Mini Skort
Cute enough to make the group chat ask where it’s from immediately. This floral embroidered linen-blend skort brings the flirty details with a mini-length overlay and fitted shorts made for vacation dinners, rooftop drinks, and last-minute plans that somehow turn into the best night.
Shop Matching Top: Coastal Vibe Floral Embroidered Tie-Front Top
Fit & Features
- Linen-blend woven fabric
- Floral embroidered pattern
- High-rise waist
- Mini-length front overlay
- Fitted shorts
- Runs true to size
Style Number/Barcode: 06303-000055
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Sleek And Flirty Cowl Neck Halter Top
This cowl neck halter top was made for nights when subtle just isn’t the mood. The plunging neckline, open back, and draped fit keep it sleek, flirty, and impossible to ignore from every angle. Style with the matching midi skirt.
Shop Matching Bottoms: Sleek And Flirty High-Slit Midi Skirt
Fit & Features
- Sleek knit fabric, high stretch
- Sleeveless plunging cowl neckline, bar strap accent
- Tie-back halter straps
- Open back, lower tie-back spaghetti straps
- Mid-length hem, draped fit
- Runs true to size
Style Number/Barcode: 06001-000594
Category Name: Vacation Looks
Price: $19.90
Availability: In Stock
Available Color: TEAL
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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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: 06001-000634
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: FUCHSIA
Available Size: XS, S, M, L
Product Badge:- Part of a Set