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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Too Busy Round Sunglasses
These sleek sunglasses give quiet confidence. The slim silhouette and dark lenses make every outfit feel a little more polished, whether you’re headed to brunch, boarding a flight, or avoiding eye contact in style.
Fit & Features
- Round slim silhouette
- Tinted lenses
- Hardware insert
Style Number/Barcode: 07008-000130
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
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Sunset Stroll Lace-Up Espadrille Wedges
These wedges were made for sunset strolls after dinner. The lace-up straps, woven platform, and hoop detail give effortless vacation allure, whether you're on a getaway or staycation.
Fit & Features
- Almond toe
- Strappy toe with hoop detail
- Espadrille platform sole
- Lace-up ankle straps
- Runs true to size
Style Number/Barcode: 07406-000068
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: TAN, BLACK
Available Size: 10
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Sunset Route Crochet Poncho
This sheer crochet poncho layers perfectly over swimwear, bridal weekend looks, or sunset dinner plans with an asymmetrical neckline and hem that keeps the whole vibe easy and elevated.
Fit & Features
- Crochet cotton-blend woven fabric
- Asymmetrical neckline
- Flowy crop-length asymmetrical hem
- Runs true to size
Style Number/Barcode: 06204-000176
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: XS/S, M/L
Product Badge:- Sale
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Mireille Leopard Chiffon Formal Dress
Special Occasion
The Mireille floor-length gown brings effortless drama to every RSVP. Designed in airy chiffon fabric with a leopard print, this A-line dress features a plunging neckline, strappy open tie back, and high front slit that moves beautifully from cocktail hour to the dance floor.
Fit & Features
- Leopard print, chiffon fabric, mesh lining
- Plunge halter neckline with bar accent
- Open back with detachable beaded chain, zipper and hook-eye closure
- Side waist cutout, hardware insert
- High front slit
- Flowy A-line floor-length silhouette
- Runs true to size
Where to Wear:
Weddings, engagement parties, vacations, honeymoons, destination celebrations, birthday dinners, cocktail soirees, and fashion-forward events.
Style Number/Barcode: 05002-001317
Category Name: Vacation Looks
Price: $129.90
Availability: In Stock
Available Color: LEOPARD
Available Size: XS, S, M, L
Product Badge:- Ships Free
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Palm Springs Bound Satin Mini Dress
This mini dress is bound for somewhere sunny. The satin finish, open back tie detail, and oversized floral print bring instant vacation drama in the best way possible. Just add sandals to complete the look.
Fit & Features
- Statement tropical floral print, satin fabric, knit lining
- Halter neckline with tie straps
- Open back with tie strap, zipper and hook-eye closure
- Form-hugging silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001219
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M
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Jennie Satin A-Line Lace-Up Formal Dress
Special Occasion
Jennie satin A-line gown skims the body before flowing into a soft, sweeping hem. The lace-up back and cascading ruffle detail bring just the right amount of drama—perfect for when you want to feel polished yet a little undone, in the best way.
Fit & Features
- Premium satin fabric, woven lining
- Cowl neckline, spaghetti straps
- Hidden side zipper and hook-eye closure
- Lace-up open back
- High front ruffled slit
- A-line floor-length silhouette
- Runs true to size
Where to Wear:
Prom, wedding guests, bridesmaids, black tie galas, formal milestone celebrations, engagement parties, destination events, anniversaries, big birthday parties, fancy showers
Style Number/Barcode: 05002-000894
Category Name: Vacation Looks
Price: $69.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L, XL
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Caught Staring Cat-Eye Sunglasses
Fit & Features
- Cat-eye design
- Plastic frame
- Built-in nose pads
- Thin metal arms, metal accents
- Tinted lenses
Style Number/Barcode: 07008-000133
Category Name: Vacation Looks
Price: $10.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
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Caught A Glance Oval Sunglasses
These oval sunglasses bring that effortlessly trendy vibe to every outfit, whether you’re styling them with a baby tee and denim or throwing them on for a last-minute coffee run.
Fit & Features
- Long oval design
- Thin metal frame
- Flexible rubber nose pads
- Wide arms
- Tinted lenses
Style Number/Barcode: 07008-000132
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Shine Clear Bangle Bracelet
The kind of accessory that makes your iced coffee and mirror selfies look instantly more on-trend. This clear acrylic bangle bracelet adds a sculptural finish to even the simplest outfit, whether you’re stacking it or letting it steal the attention solo.
Fit & Features
- Clear acrylic material
- Chunky bangle bracelet silhouette
- Faceted asymmetric design
Style Number/Barcode: 07003-000250
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: In Stock
Available Color: CLEAR
Available Size: NS
Product Badge:- Sale
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Tropical Soiree Flower Earrings
These earrings feel like they belong with a sunset dinner reservation. The glossy orchid design adds the perfect pop of color to pull the whole vacation mood together.
Fit & Features
- Flower orchid design
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000347
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: ORANGE, WHITE, BLUE
Available Size: NS
- Flower orchid design
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Island On The Mind Tropical Tank Top
This top feels like booking the trip. The halter neckline and oversized floral print bring instant vacation vibes, whether you’re headed beachside or just dressing like it.
Fit & Features
- Knit stretchy fabric
- Tropical floral print
- Halter neckline, tie straps
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06002-000628
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: TEAL
Available Size: XS, S, M, L
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Just Enough Drama Hammered Drop Earrings
These hammered drop earrings bring that bold, sculptural vibe to dinner reservations, rooftop cocktails, and every last-minute “wait, I’m coming too” text.
Fit & Features
- Drop silhouette
- Hammered metal design
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000354
Category Name: Vacation Looks
Price: $9.90
Availability: Out of Stock
Product Badge:- Ships Free
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Sultry Tease Open Back Top
This top was basically made for parties, dancing, and taking “just one pic” that turns into fifty. The draped halter neckline and chunky ring details bring the perfect mix of sultry and effortless to your look.
Fit & Features
- Slinky knit fabric
- Cowl halter neckline, hoop ring inserts
- Open tie back design
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000661
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: TEAL
Available Size: XS, S, M, L
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Cabana Crush Chevron Sarong Wrap
Booked the cabana before you even finished packing. This sarang wrap bring major resort mood with its retro-inspired chevron print, tie-waist design, and matching pieces that was made for poolside photos.
Shop The Matching Top: Cabana Crush Chevron Bikini Top
Shop The Matching Bottoms: Cabana Crush Chevron Bikini BottomsFit & Features
- Chevron print, sleek knit fabric
- Tie-waist design
- Wrap styling
- Runs true to size
Style Number/Barcode: 07105-000048
Category Name: Vacation Looks
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cabana Crush Chevron Bikini Bottoms
Booked the cabana before you even finished packing. These bikini bottoms bring major resort mood with its retro-inspired chevron print, hoop inserts, and matching pieces that was made for poolside photos.
Shop The Matching Top: Cabana Crush Chevron Bikini Top
Shop The Matching Sarang: Cabana Crush Chevron Sarong WrapFit & Features
- Chevron print, sleek knit-lined fabric
- Hoop insert waist detail
- Cheeky cut
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000047
Category Name: Vacation Looks
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Diamond District Arm Cuff
Minimal outfit, dramatic accessories, problem solved. This sleek arm cuff wraps around with sculptural shine and rhinestone details that catch the light from every angle.
Fit & Features
- Textured polished finish
- Open wrap silhouette
- Rhinestone accents
- Sculptural design
Style Number/Barcode: 07003-000232
Category Name: Vacation Looks
Price: $13.90
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Style Resin Bangle Bracelet Set
Serving stacked wrist moments with zero effort required. This resin bangle bracelet set adds the perfect pop to tanks, oversized button-downs, and every last-minute outfit that somehow still looks planned.
Fit & Features
- Two-pack bangle bracelet set
- Resin material
- Smoothy, glossy finish
- Wide designs
Style Number/Barcode: 07003-000308
Category Name: Vacation Looks
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
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Extra Chic Pearl Charm Bracelet
A little extra in the best way possible. This pearl charm bracelet brings the layered look without the styling stress, thanks to the chunky chain and mixed charms that make every outfit feel way more chic.
Fit & Features
- Chunky chain
- Beaded, faux pearl, and circular textured charms with mini rhinestones
- Lobster clasp closure with extender
Style Number/Barcode: 07003-000309
Category Name: Vacation Looks
Price: $11.90
Availability: Out of Stock
Product Badge:- Ships Free
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Artsy Edge Flower Statement Cuff
This flower statement cuff understood the assignment the second you put it on. The sculpted design and textured metal finish bring an artsy edge that makes even a basic outfit feel styled.
Fit & Features
- Thin textured metal silhouette
- Flower sculpted statement design
- Hinge closure
Style Number/Barcode: 07003-000310
Category Name: Vacation Looks
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
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Bethany Tropical Bead A-Line Mini Dress
Special Occasion
The Bethany mini dress was made for sunny destinations. This beaded mesh mini dress features a tropical pattern, an open back, and a flattering A-line silhouette that brings just the right amount of getaway glamour.
Fit & Features
- Tropical beaded pattern, mesh fabric, smooth lining
- Square neckline
- Spaghetti straps
- Cutout back detail
- A-line mini-length silhouette
- Runs true to size
Where to Wear:
Vacations, honeymoons, birthday dinners, getaways, date nights, parties
Style Number/Barcode: 05001-000656
Category Name: Vacation Looks
Price: $89.90
Availability: In Stock
Available Color: CORAL
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free
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Vacation Flirt Knit Cutout Maxi Dress
Serving vacation flirt and trendy vibes. This knit maxi dress hugs in all the right places with lace-up cutouts, a plunging halter neckline, and an open back that knows exactly what it’s doing.
Fit & Features
- Knit fabric with flame stitch pattern
- Sleeveless plunging V-neckline, beaded strap
- Tie-back halter straps
- Lace-up side cutouts
- Open back, lower tie-back spaghetti straps
- Back zipper and hook-eye closure
- Maxi-length bodycon silhouette, back slit accent
- Runs true to size
Style Number/Barcode: 05102-000606
Category Name: Vacation Looks
Price: $48.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
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On Your Mind Abstract Print Mesh Mini Dress
This mini dress doesn’t wait for compliments. The abstract print, plunging halter neckline, and ruched mesh fit were made for making an entrance and staying on everyone’s mind.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Abstract print
- Sleeveless plunging scoop neckline
- Tie-back halter straps, open back
- Ruched wrap-front design, hardware accent, center sash
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-000641
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Sunkissed Stunner Halter Maxi Dress
Vacation mode called, and this maxi dress already answered. With a plunging halter neckline, bold cutout details, and a flowy front slit silhouette, this maxi dress was made for beachside brunches, sunny getaways, and weekend plans.
Fit & Features
- Artsy print, woven fabric
- Halter neckline
- Strappy cutout bodice, back zipper and hook-eye closure
- High front slit
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000645
Category Name: Vacation Looks
Price: $27.97 $59.90
On Sale: Yes
Availability: In Stock
Available Color: TAUPE
Available Size: XS, S, L
Product Badge:- Sale
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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