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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Palm Paradise Halter Romper
Booked the trip, found the outfit. This tropical leaf print romper combines a plunging halter neckline, bead accents, and a flirty open tie back with a tiered ruffle hem made for vacations, resort destinations, and weekend escapes.
Fit & Features
- Palm print, mesh fabric, knit lining
- Plunge halter neckline, beaded strap, tie straps
- Open tie-back
- Tiered ruffle mini-length hem
- Built-in shorts lining
- Runs true to size
Style Number/Barcode: 06503-000307
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Blooming Agenda Floral Mesh Maxi Skirt
Booked, busy, and somehow still best dressed. This floral mesh maxi skirt brings a high-cut back slit and a curve-hugging fit that pairs perfectly with the matching bustier for any RSVP-worthy plan on your calendar.
Shop Matching Top: Blooming Agenda Floral Mesh Strapless Bustier
Fit & Features
- Mesh fabric with full-length knit lining, high stretch
- Large floral print
- High-rise waist
- High-cut back slit
- Maxi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06501-000183
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Polished Bloom Wrap Flower Arm Cuff
The arm cuff accessory that makes a simple outfit look styled in seconds. Featuring a wrap silhouette with sculpted floral accents, this arm cuff brings a romantic, fashion-forward feel to everything from vacation looks to special occasion dresses.
Fit & Features
- Metal wrap-around design
- Flower accents with rhinestone-embellished center insets
- Polished finish
Style Number/Barcode: 07003-000241
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: SILVER
Available Size: NS
Product Badge:- New Arrival
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Pretty Shine Layered Stone Belly Chain
Tiny details, major outfit payoff. This layered stone belly chain adds the prettiest shine to low-rise denim, bikinis, matching sets, and every last minute “wait… this actually eats” look.
Fit & Features
- Two-row layered cross-over design
- Dainty chains
- Clear stone accents
- Lobster clasp closure with extender
- Adjustable fit
Style Number/Barcode: 07002-000446
Category Name: Vacation Looks
Price: $11.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival
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Caught Up Beaded Crop Top
The top that makes every mirror selfie worth posting. This crop top brings just the right amount of shine, serving a flattering curve-hugging fit and a striking open back that keeps all eyes on you.
Shop Matching Bottoms: Caught Up Beaded Maxi Skirt
Fit & Features
- Slinky knit stretchy fabric
- Plunge halter neckline
- Strappy beaded embellished open back
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000694
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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On Repeat Layered Stone Belly Chain
A little sparkle at the waist changes the whole outfit. This layered stone belly chain brings just enough shimmer to low-rise denim, swim looks, and going-out 'fits.
Fit & Features
- Two-row layered cross-over design
- Dainty chains
- Clear stone accents
- Lobster clasp closure with extender
- Adjustable fit
Style Number/Barcode: 07002-000443
Category Name: Vacation Looks
Price: $10.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival
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Better Together Bangle Bracelet Set
The wrist stack practically styled itself. This bangle bracelet set features three resin bangles in varying silhouettes, making it the easiest way to add dimension and personality to any outfit.
Fit & Features
- Three-pack bangle bracelet set
- Resin material
- Varying silhouettes
Style Number/Barcode: 07003-000259
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: MULTI
Available Size: NS
Product Badge:- New Arrival
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Aloha For Now Flower Hair Pin Set
Say aloha to your new vacay-inspired look. These hibiscus flower hair pins add a playful tropical touch to ponytails, buns, and beach-day looks with a bloom for every mood.
Fit & Features
- Hibiscus flower designs
- Metal clip closures
- Three-pack set
Style Number/Barcode: 07006-000159
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: MULTI
Available Size: NS
Product Badge:- New Arrival
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Low Key Luxe Tinted Sunglasses
The kind of sunglasses that make even a simple outfit feel a little more polished. Featuring slim metal frames and warm brown-tinted lenses, this pair delivers a sleek, vintage-inspired finish.
Fit & Features
- Sleek round frames
- Rubber nose supports
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000165
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
Product Badge:- New Arrival
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Lei It On Me Flower Chain Belt
The outfit was cute, then the flower chain belt showed up. Finished with sculpted hibiscus blooms, this statement belt brings vacation-ready charm to bottoms, swimsuits, and everything packed in between.
Fit & Features
- Hibiscus flower designs
- Polished shine finish
- Chain
- Lobster clasp closure
Style Number/Barcode: 07301-000397
Category Name: Vacation Looks
Price: $16.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival
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Destination Darling Floral Crop Top
Vacation mode looks good on you. This floral halter top pairs a draped neckline with an open back silhouette for the kind of outfit perfect for every getaway plan.
Fit & Features
- Tropical floral print, stretchy knit fabric
- Cowl halter neckline with tie straps
- Open back
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000675
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Paradise Glow Tropical Sequin Beaded Mini Dress
Vacation booked or not, this tropical sequin beaded mini dress is already packed for the plot. The stretchy lined mesh hugs close with a square neckline, strappy back cutout, and just enough shine to make every entrance feel intentional.
Fit & Features
- Tropical printed mesh fabric with knit lining, high stretch
- Sequin and beaded swirl embroidered pattern
- Sleeveless square neckline
- Adjustable spaghetti straps
- Lower back cutout
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-000878
Category Name: Vacation Looks
Price: $59.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Meet Me In Maui Mesh Maxi Dress
Covered in oversized tropical blooms and saturated sunset shades, this mesh midi dress brings vacation energy, whether you're headed to dinner by the water or a relaxing cruise.
Fit & Features
- Tropical print, lined mesh fabric with stretch
- Strapless neckline
- Bodycon silhouette
- Fitted maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000763
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: PINK
Available Size: S, M, L
Product Badge:- New Arrival
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Ruffle Rush Tropical Floral Mini Dress
Booked trip or just booking attention, this tropical floral ruffle mini dress gets the invite. The stretchy lined mesh, halter cowl neckline, open back, and flowy ruffled sash bring flirty movement with a fitted A-line shape.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Tropical floral print
- Sleeveless cowl neckline
- Tie-back halter straps, open back, lower tie-back spaghetti straps
- Asymmetric tiered ruffled design, ruffled side sash accent
- Mini-length hem, fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000624
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Flirty Forecast Halter Ruffle Mini Dress
Cue the entrance, this halter ruffle mini dress came ready to flirt. The high-stretch knit sculpts with ruching through the waist, a deep V-neckline, and tiered ruffles that bring movement without overthinking the outfit.
Fit & Features
- Sleek knit fabric, high stretch
- Sleeveless deep V-neckline, beaded hardware accents
- Tie-back halter straps, partially open back
- Ruched detailing, drop waist
- Tiered ruffled design, mini-length hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05103-001139
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: PINK, TURQUOISE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Wild Card Cowl Halter Mini Dress
This dress doesn't do subtle, and that's exactly the point. The draped cowl neckline, daring open back, and mixed animal print make this halter mini dress the first thing you'll reach for when packing for vacation or nights out.
Fit & Features
- Mixed animal print, knit-lined fabric
- Plunge cowl halter neckline, tie straps
- Open tie back
- Bodycon mini-length fit
- Runs true to size
Style Number/Barcode: 05103-001060
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: GRAY
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Hailie Tropical Floral Lace Formal Dress
Special Occasion
Designed for the guest list that calls for something unforgettable, the Hailie dress brings together tropical lace, cascading ruffles, and a sculptural orchid accent for a look that feels equal parts romantic and statement-making. The plunging halter neckline, open back, and mermaid silhouette create striking movement from every angle.
Fit & Features
- Tropical floral print, lace fabric, smooth knit lining
- Plunge ruffled halter neckline, tie straps
- Front tropical flower pin
- Open tie-back, lower zipper and hook-eye closure
- Cascading ruffle trim
- Mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Destination weddings, vacations, honeymoons, resorts, cruises, engagement parties, cocktail events, birthday dinners, date nights, summer galas, yacht parties
Style Number/Barcode: 05002-001583
Category Name: Vacation Looks
Price: $79.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
Product Badge:- Ships Free
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Seaside Stunner Halter Maxi Dress
The kind of dress that makes an entrance. With a textured finish, beaded cutout details, and a sleek halter neckline, this maxi dress is perfect for vacations, bridal celebrations, and brunch dates.
Fit & Features
- Sweater knit fabric, knit lining
- Halter neckline, tie straps
- Cutout bust with beaded accents
- Center back slit
- Bodycon maxi silhouette
- Runs true to size
Style Number/Barcode: 06005-000326
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Beach Treasures Earrings Pack
This 20-piece earring set is packed with beach-inspired details, from shells and starfish to palms and pearls, making it the perfect mix-and-match collection for vacations, weekend plans, and everyday styling.
Fit & Features
- 20-piece earring set
- Various styles and beach-inspired designs
- Faux pearls and rhinestone embellishments
- Polished metal finish
- Post-back and omega closures
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000416
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival
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Catch The Vibe Beaded Halter Top
The outfit did not come to play, and neither did this top. Featuring beaded string detailing, a halter neckline, and an open back design, this crop top brings the sass to denim shorts and sandals.
Fit & Features
- Knit fabric
- Square halter neckline, tie straps
- Open tie-back
- Beaded front design
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06001-000523
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Snap Ready Rectangle Phone Grip
Your phone just got a better grip on the situation. This rectangle phone grip keeps scrolling, selfies, and content checks feeling way more secure without adding bulk.
Fit & Features
- Flexible rubber material
- Rectangle shape
- Raised suction cup design
Style Number/Barcode: 07308-000106
Category Name: Vacation Looks
Price: $6.90
Availability: In Stock
Available Color: CLEAR, BLACK, PINK
Available Size: NS
Product Badge:- New Arrival
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Georgina Glitter Cutout Formal Dress
Special Occasion
The Georgina formal dress blends shimmering glitter knit fabric with a sleek, form-hugging long silhouette. A sleeveless halter sweetheart neckline with hardware stone and ball inserts, side cutout bodice, hoop detail, and high side slit create a look that feels equal parts polished and unforgettable.
Fit & Features
- Glitter knit fabric, smooth knit lining, high stretch
- Halter neckline, padded bra cups, hardware stone and ball inset
- Adjustable spaghetti straps
- Side bodice cutout, hoop waist insert
- High side slit
- Form-hugging long-length silhouette
- Runs true to size
Where to Wear:
Destination weddings, cocktail celebrations, birthday dinners, vacations, honeymoons, resort getaways, date nights, luxury cruises, yacht parties
Style Number/Barcode: 05002-001423
Category Name: Vacation Looks
Price: $69.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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After Hours Bloom Floral Maxi Dress
Sleek, sculpted, and made to linger in the memory. This mesh maxi dress features a square neckline and a curve-hugging fit that feels elevated enough for dressy occasions and vacay.
Fit & Features
- Stretch mesh fabrication with smooth lining, floral print
- Spaghetti straps with a square neckline
- Fitted bodice through the hips
- Curve-hugging fit, flared maxi hem
- Runs true to size
Style Number/Barcode: 05101-000721
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L, XL
Product Badge:- New Arrival
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Vivid Escape Ruffle Halter Mini Dress
A bold mix of prints and flowing movement makes this one impossible to overlook. This printed mini dress features a halter neckline, plunging front, and layered ruffle hem that creates dimension with every step. Perfect for vacations, day parties, and warm-weather plans that deserve something a little more memorable.
Fit & Features
- Lined mesh fabric
- Halter neckline with plunging front detail
- Mixed floral and animal print design
- Form-hugging fit
- Layered ruffle mini hem with cascading side ruffle
- Runs true to size
Style Number/Barcode: 05103-000937
Category Name: Vacation Looks
Price: $46.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
Product Badge:- New Arrival