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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Vacay Slay Shell-Trim Crochet Mini Skirt
The kind of skirt that instantly creates a vacay slay. This crochet mini skirt pairs a barely-there open knit with shell-trim details for a look that was made for beach clubs, oceanside strolls, and spontaneous getaway plans. Style with the matching crop top.
Shop Matching Top: Vacay Slay Shell-Trim Crochet Crop Top
Fit & Features
- Crochet knit fabric, moderate stretch
- Mid-rise waist
- Mini-length hem, shell trim fringe
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06501-000146
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: OLIVE
Available Size: S, M, L
Product Badge:- Part of a Set
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Vacay Slay Shell-Trim Crochet Crop Top
The kind of top that instantly creates a vacay slay. This crochet crop top pairs a barely-there open knit with shell-trim details for a look that was made for beach clubs, oceanside strolls, and spontaneous getaway plans. Style with the matching mini skirt.
Shop Matching Bottoms: Vacay Slay Shell-Trim Crochet Mini Skirt
Fit & Features
- Crochet knit fabric, lined bust, moderate stretch
- Sleeveless deep V-neckline
- Halter spaghetti straps
- Partially open back
- Cropped hem, shell trim fringe
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-000373
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: OLIVE
Available Size: S, M, L
Product Badge:- Part of a Set
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Poolside Priority Tie Front Top
This top practically comes with a boarding pass. Featuring a flirty tie front crop top, flutter sleeves, and a cropped length, it's the kind of look that belongs at pool parties, vacations, and every photo op in between.
Shop Matching Bottoms: Poolside Priority Slit Maxi Skirt
Fit & Features
- Stretchy knit fabric
- Tie-front neckline
- Flutter short sleeves
- Cropped length hem
- Runs true to size
Style Number/Barcode: 06202-000110
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Katana Abstract A-Line Formal Dress
Special Occasion
Float through the evening like you already belong on the best-dressed list in The Katana, a sweeping statement made for unforgettable arrivals. The abstract print mesh fabric, plunge halter V-neck, and open back bring a striking contrast to the soft movement of the A-line floor-length silhouette and front slit.
Fit & Features
- Abstract print, mesh fabric, knit stretchy lining
- Plunge halter V-neckline with tie straps, padded bra cups
- Open back, lower zipper and hook-eye closure
- Side ruched seams
- Front slit
- A-line floor-length silhouette
- Runs true to size
Where to Wear:
Weddings, galas, engagement parties, art galleries, cocktail soirees, birthday dinners, vacations, destination celebrations
Style Number/Barcode: 05002-000879
Category Name: Vacation Looks
Price: $79.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, XL
Product Badge:- Ships Free
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Sweet Escape Abstract Floral Halter Top
Vacation mode: activated. This floral mesh halter crop top features a plunging neckline, ruched waist detail, and an open-back design that was made for rooftop dinners, weekend getaways, and every plan worth dressing up for.
Shop Matching Bottoms: Sweet Escape Abstract Floral Ruffle Skort
Fit & Features
- Lined mesh fabrication
- Sleeveless halter V-neckline
- Open back with adjustable neck tie
- Abstract floral pattern
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-000838
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Step Into It Wedge Sandals
A little height, a lot of outfit potential. These faux leather thong wedges bring an easy lift to everything from vacation looks to weekend dinner plans without missing a step.
Fit & Features
- 3.5" wedge heel
- Square toe
- Thong toe strap
- Cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07406-000046
Category Name: Vacation Looks
Price: $29.90
Availability: Out of Stock
Product Badge:- Ships Free
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Weekend Away Strapless Maxi Dress
This chevron maxi dress hugs in all the right places with a sleek strapless neckline and leg-baring side slit that was practically made for resort dinners, sunset cocktails, and strolling the beachside town.
Fit & Features
- Chevron pattern, crochet fabric, smooth knit lining
- Strapless neckline
- Side slit
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000595
Category Name: Vacation Looks
Price: $20.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- Sale
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Meet Me At Sunset Floral Mini Dress
Designed with a plunging halter neckline, dramatic open back, and flirty ruffle hem, this mini dress features an oversized floral print and cascading side sash made for vacations, going night, and flirty weekend looks.
Fit & Features
- Floral print, mesh fabric, knit lining
- Plunge halter neckline, bar accent, tie straps
- Curve-hugging fit
- Ruffled side sash
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000969
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M
Product Badge:- Sale
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Rynlee Strapless Mermaid Formal Dress
Special Occasion
Made for the kind of evening that lingers long after the last dance, Rynlee slinky knit mermaid gown blends sleek glamour with striking detail. The strapless neckline, wooden hoop insert cutout bust, and flowing center front sash create a sculpted silhouette that feels equal parts polished and unforgettable.
Fit & Features
- Slinky knit fabric, knit lining
- Strapless neckline
- Wooden hoop insert, cutout, center front sash
- Mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Destination weddings, engagement parties, vacations, honeymoons, resort getaways, cocktail parties, date nights, birthday dinners, formal celebrations
Style Number/Barcode: 05002-001603
Category Name: Vacation Looks
Price: $69.90
Availability: In Stock
Available Color: SAGE, BROWN
Available Size: XS, S, M, L, XL
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Rooftop In Santorini Maxi Dress
The dress equivalent of a first class upgrade. With a plunging halter neckline, statement bead details, and a low open back, this maxi dress was made for resort dinners, oceanfront cocktails, and making every entrance feel a little more unforgettable.
Fit & Features
- Mesh fabric, knit lining
- Plunge halter neckline
- Open back design, lower zipper and hook-eye closure
- Front colored stone button accents
- Ruched drop waist panel
- Side slit
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-001163
Category Name: Vacation Looks
Price: $21.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ocean View Floral Beaded Mini Dress
This is the dress that ends up in every vacation photo. With a draped cowl neckline, floral beading, and an open tie-back design, this bodycon mini dress was made for dinner reservations that turn into unforgettable nights.
Fit & Features
- Floral print, beaded mesh fabric, sewn-in knit lining
- Cowl neckline
- Spaghett straps
- Open tie-back
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05103-000830
Category Name: Vacation Looks
Price: $59.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
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Dinner At Eight Floral Maxi Dress
Some dresses get compliments. This one starts conversations. Featuring an elegant cowl neckline, an open-back halter design, and oversized floral artwork, this maxi dress was made for vacation dinners, wedding guest RSVPs, and every plan that deserves a dramatic entrance.
Fit & Features
- Tropical floral print, mesh fabric, knit lining
- Cowl halter neckline
- Open tie-back
- Side slit
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000678
Category Name: Vacation Looks
Price: $19.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M
Product Badge:- Sale
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Booked And Beachside Maxi Dress
This is the dress you pack first and plan the trip around later. Featuring a statement hardware detail, dramatic front cutout, and leg-lengthening slit, this maxi dress was made for sunset dinners, oceanfront cocktails, and every photo op.
Fit & Features
- Smooth knit fabric, stretchy
- Halter neckline, tie straps
- Front hardware insert and cutout bodice
- Ultra-high front slit
- Flowy A-line maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-000790
Category Name: Vacation Looks
Price: $49.90
Availability: Out of Stock
Product Badge:- Ships Free
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Sunshine On Schedule Halter Romper
Your vacation itinerary just found its outfit. This plunging halter romper brings all the resort energy with a vibrant abstract print, a cinched waist, and a flirty skater silhouette perfect for tropical resorts, sunny weekends, and beachside brunch.
Fit & Features
- Abstract print, knit fabric
- Plunge halter neckline, tie straps
- Open back design
- Cinched waist
- Flowy skater hem
- Built-in shorts knit lining
- Runs true to size
Style Number/Barcode: 06503-000329
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
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Angelique Abstract Print Mermaid Formal Dress
Special Occasion
The Angelique formal dress is the kind of gown that makes every entrance feel mystical. Crafted from printed mesh in a sculpting mermaid silhouette, this floor-length dress features a plunging halter neckline, daring cutouts, and delicate beaded trim that catches the light from every angle.
Fit & Features
- Abstract print, mesh-lined fabric
- Halter V-neckline, spaghetti straps
- Open tie-back and strappy accents
- Cutout bodice with beaded-embellished straps
- Mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Vacations, honeymoons, resort getaways, birthday dinners, cocktail parties, destination weddings, formal cruise events, and fashion-forward occasions.
Style Number/Barcode: 05002-001579
Category Name: Vacation Looks
Price: $89.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free
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Endless Summer Abstract Maxi Dress
This dress looks like it was made for golden hour by the water. Featuring a dreamy abstract print, draped cowl neckline, and beaded halter straps, it brings effortless vacation energy to every RSVP.
Fit & Features
- Abstract print, mesh knit fabric, sewn-in knit lining
- Square halter neckline, beaded tie straps
- High side slit
- Form-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000811
Category Name: Vacation Looks
Price: $20.97 $45.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE-2
Available Size: XS, S
Product Badge:- Sale
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Make Them Stare Mesh Slit Maxi Dress
This is the dress that captures all the attention on vacations and weekend escapes. Featuring a bold floral print, curve-hugging fit, and a leg-baring side slit, it's equal parts sultry and unforgettable.
Fit & Features
- Statement floral print, mesh-lined fabric
- Strapless tube neckline
- High side slit
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-001170
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L, XL
Product Badge:- Sale
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Daydreaming Floral Knit Dress
Equal parts cozy and cute, this floral midi dress is made for brunch, weekend plans, and vacations. The oversized floral design gives it a playful statement feel, while the strapless silhouette keeps the look effortlessly polished.
Fit & Features
- Statement floral print, sweater knit fabric
- Strapless tube neckline
- Form-hugging fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000411
Category Name: Vacation Looks
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
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Bold Entrance One-Shoulder Mini Dress
Consider this your excuse to make an entrance. This one-shoulder mini dress hugs in all the right places with an asymmetric cutout, ruched detailing, and a bold side sash that does all the talking.
Fit & Features
- Slinky knit fabric, high stretch, sewn-in lining
- One-shoulder neckline, long fitted sleeve
- Asymmetric waist cutout
- Ruched detailing
- Side sash accent
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-000864
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M
Product Badge:- Sale
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Stacked To Perfection Bangle Bracelet Set
The outfit looked good, then these showed up. This bangle bracelet set pairs a sleek resin bangle with a polished metal bangle for an effortless stacked look that works from coffee runs to dinner reservations.
Fit & Features
- Two-pack bangle bracelet set
- Resin bangle
- Metal bangle
Style Number/Barcode: 07003-000258
Category Name: Vacation Looks
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Mood Bangle Bracelet Set
Proof that the right accessories can change the whole mood. This bangle bracelet set combines a sleek metal bangle with an asymmetric resin bangle for a stacked look that instantly pulls an outfit together.
Fit & Features
- Two-pack bangle bracelet set
- One metal bangle
- One asymmetric resin bangle
Style Number/Barcode: 07003-000262
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Caught Looking Cat-Eye Sunglasses
Serving side glances and stealing attention without saying a word. These cat-eye sunglasses feature tinted lenses and a sleek retro-inspired shape that instantly pulls any outfit together, from coffee runs to rooftop plans.
Fit & Features
- Cat-eye shape
- Plastic frame
- Built-in nose pads
- Tinted lenses
Style Number/Barcode: 07008-000131
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
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Meet Me In Miami Halter Mini Dress
From cocktails to beachside dinners, this is the dress that makes vacation photos look even better. This tropical mesh mini dress is serving destination energy with a draped cowl neckline, open-back detail, and a statement sash that moves with every step.
Fit & Features
- Abstract print, mesh-lined fabric
- Halter cowl neckline
- Open back design
- Curve-hugging silhouette
- Ruffled trim mini-length hem with a cascading drape
- Runs true to size
Style Number/Barcode: 05103-001080
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: MULTI
Available Size: XS, S
Product Badge:- Sale
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After Hours Aura Beaded Lace Bra Top
All sparkle, no subtlety. This beaded lace bra top brings the drama with a halter neckline, pearl-inspired draping, and chain body detailing made for going out, festival fits, and photo-ready plans.
Fit & Features
- Lined lace fabrication
- Beaded embellishments
- Halter neckline with bra cups
- Draped fringe trim and chain body detailing
- Open back with adjustable tie closures
- Runs true to size
Style Number/Barcode: 06001-000564
Category Name: Vacation Looks
Price: $42.90
Availability: Out of Stock
Product Badge:- Ships Free