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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Rylan Floral Linen Cutout A-Line Dress
Special Occasion
Made for sun-drenched celebrations, the Rylan floral linen A-line dress brings effortless glamour to every RSVP. The plunging neckline and sculpted cutout detail give the flowy silhouette a modern feel that’s perfect for vacations, birthday dinners, and chic brunch plans.
Fit & Features
- Linen-blend woven fabric
- Floral print, piping contrast design
- Sleeveless V-neckline, tank shoulder straps
- Tie-front detail, asymmetric front waist cutout, side cutouts
- Open back, tie-back strap, lower zipper with hook-eye closure
- Floor-length A-line silhouette
- Runs true to size
Where to Wear:
Birthday celebrations, vacations, honeymoons, summer parties, and brunch with the girls.
Style Number/Barcode: 05002-001150
Category Name: Vacation Looks
Price: $94.90
Availability: In Stock
Available Color: WHITE, PRINT
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free
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Vacay Serve Tropical Floral Mesh Mini Dress Coverup
Serving vacation pics without even trying. This tropical floral mesh mini dress hugs in all the right places with a sheer bodycon fit that was made for beach clubs, rooftop drinks, and every “wait, where’d you get that?” moment.
Fit & Features
- Sheer mesh fabric, high stretch
- Large tropical floral print
- Sleeveless crew neckline
- Tank shoulder straps
- Ruched draped front design, O-ring accent
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 07105-000059
Category Name: Vacation Looks
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chantelle Chevron A-Line Formal Dress
Special Occasion
There’s something effortlessly captivating about a dress that moves with ease from ceremony to afterparty, and the Chantelle chevron crochet gown does exactly that. Designed with beaded spaghetti straps and a strappy open tie back, the A-line floor-length silhouette feels polished with just the right amount of allure.
Fit & Features
- Chevron crochet fabric, stretchy knit lining
- V-neckline
- Spaghetti straps with beaded accents
- Strappy open tie back design, lower zipper and hook-eye closure
- A-line floor-length silhouette
- Runs true to size
Where to Wear:
Destination weddings, vacations, honeymoons, resorts, dinner parties, semi-formal events and occasions
Style Number/Barcode: 05002-001562
Category Name: Vacation Looks
Price: $29.97 $84.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L, XL
Product Badge:- Sale
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Wild Mood Zebra Print Mesh Bodycon Mini Dress
For the nights when subtle just isn’t on the mood board. This zebra print mesh mini dress hugs in all the right places with a bodycon fit, open back details, and a draped silhouette that was made for late RSVP texts and last-minute plans.
Fit & Features
- Zebra-printed mesh fabric with knit lining, high stretch
- Sleeveless deep V-neckline, wrap-front design
- Halter tie-back straps
- Open back, tie-back spaghetti straps, draped lower back
- Relaxed fit bodice, drop waist design
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-000821
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: GRAY
Available Size: XS, S, M, L
- Zebra-printed mesh fabric with knit lining, high stretch
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Sun Chaser Crochet Shorts
Instant vacation mode, no ticket required. These crochet shorts feature a low-rise waist and form-hugging fit that feels bold, effortless, and made for warm days that turn into golden-hour plans. Shop the matching top.
Shop Matching Top: Sun Chaser Crochet Halter Top
Fit & Features
- Crochet knit fabric with a textured feel
- Low-rise waist
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06303-000044
Category Name: Vacation Looks
Price: $13.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: RED
Available Size: M, L
Product Badge:- Sale
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Retro Replay Printed Kitten Mules
These printed mules are basically a conversation starter in shoe form. The swirled retro print and sleek kitten heel give every outfit a statement finish.
Fit & Features
- Kitten heel
- Square toe
- Wide curved strap
- Cushioned insole
- Printed design
- Runs true to size
Style Number/Barcode: 07401-000735
Category Name: Vacation Looks
Price: $28.90
Availability: Out of Stock
Product Badge:- Ships Free
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Poolside Playlist Tropical Flower Heels
Built for rooftop selfies, vacation nights, and that “where’d you get those?” moment. These tropical flower heels bring the perfect mix of playful and glam with a barely-there fit that still makes a statement.
Fit & Features
- Metallic faux leather material
- Open square toe
- Tropical flower appliqué detail
- Stiletto heel with flat platform
- Runs true to size
Style Number/Barcode: 07401-000655
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: PINK
Available Size: 5.5, 6.5
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Salty Air Crochet Halter Top
Salty air, summer vibes. This crochet halter top brings an easy beach town style with a flirty fit that works from brunch to golden hour cocktails. Pair with the matching mini skort.
Shop Matching Bottoms: Salty Air Crochet Mini Skort
Fit & Features
- Crochet fabric, moderate stretch, bust lining
- Sleeveless plunging V-neckline
- Halter strap
- Open back, lower tie-back spaghetti straps
- Front flyaway design
- Runs true to size
Style Number/Barcode: 06003-000350
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Salty Air Crochet Mini Skort
Salty air, summer vibes. This crochet mid-rise mini skort brings an easy beach town style with a flirty fit that works from brunch to golden hour cocktails. Pair with the matching halter top.
Shop Matching Top: Salty Air Crochet Halter Top
Fit & Features
- Crochet fabric, stretchy knit built-in shorts lining
- Mid-rise waist
- Hidden side zipper and hook-eye closure
- Form-hugging fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06303-000056
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Serving Shine Sequin Mini Skort
Serving stylish shine and glam girl energy. This sequin mini skort brings the drama in the best way, with hidden shorts underneath so you can dance, pose, and move like you mean it.
Fit & Features
- Woven fabric with knit lining
- All-over chunky sequin embroidery
- High-rise waist, side zipper and hook-eye closure
- Mini-length overlay
- Hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06403-000150
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: PINK
Available Size: L
Product Badge:- Best Seller
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Sun Plans Bow Flat Sandals
Booked for sunshine and easy outfits. These bow flat sandals are your go-to for everyday styling, casual occasions, and vacations that perfectly complement every look.
Fit & Features
- Square toe
- Wide strap with statement bow tie
- Luxe fit cushioned insole
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-000072
Category Name: Vacation Looks
Price: $18.90
Availability: In Stock
Available Color: WHITE
Available Size: 5.5, 7.5, 8, 8.5
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Heat Check Bandage Knit Bodycon Mini Dress
Warning: this dress doesn’t do low profile. The plunging halter neckline and sculpting bodycon fit hug your curves and showcase your figure, made for rooftop dinners, birthday reservations, and every plan worth dressing up for.
Fit & Features
- Bandage knit fabric, moderate stretch
- Sleeveless plunging V-neckline
- Halter straps
- Partially open back, zipper closure
- Mini-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-000817
Category Name: Vacation Looks
Price: $59.90
Availability: Out of Stock
Product Badge:- Ships Free
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Jasmine Halter Slit Formal Dress
Special Occasion
Made for the kind of night that starts with compliments and ends with everyone asking where you found it, the Jasmine column dress delivers a striking silhouette with effortless allure. The halter neckline, cascading hardware, and side slit create a bold yet polished look that feels made for destination soirées and RSVP moments alike.
Fit & Features
- Texture knit fabric, smooth knit stretchy lining
- Halter cutout plunge neckline with chunky hardware
- High side slit
- Column silhouette
- Long-length hem
Where to Wear:
Bridal celebrations, bachelorettes, destination weddings, beach weddings, beach clubs, vacations, honeymoons, birthday dinners, resorts, yacht parties
Style Number/Barcode: 05002-001664
Category Name: Vacation Looks
Price: $29.97 $69.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L, XL
Product Badge:- Sale
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Vacation Flirt Striped Mini Dress
A little flirty on vacay without even trying. This striped bodycon dress hugs close with a strapless tube fit, front cutout neckline, and beaded strap accents that give you a stylish look.
Fit & Features
- Striped pattern, crinkle cotton-blend knit fabric
- Strapless tube neckline
- Front cutout with beaded strap accents
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000740
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, M, L
Product Badge:- Best Seller
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Sweetly Calculated Lace Trim Mini Dress
A little romance, a little edge. This halter mini dress hugs through the bodice, flares into an easy A-line shape, and finishes with lace trim that makes it feel styled even before you add heels.
Fit & Features
- Mesh-lined fabric, lace trim
- Halter neckline
- Partial open back
- Bodycon A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 05103-001043
Category Name: Vacation Looks
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
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Vacation Pending Drop Hoop Earrings
The kind of drop hoop earrings that make every outfit look like it came with a boarding pass. Lightweight with a statement shape, they’re made for rooftop dinners, beach clubs, and last-minute “wait, where’d you get those?” texts.
Fit & Features
- Resin material
- Round stud
- Rectangle accent
- Drop hoop design
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000424
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Postcard Crush Floral Corset Top
Pretty enough for vacation photos. This lace-up corset top effortlessly sculpts your figure with flexible boning inserts, while the crop hem makes it stylish with any bottoms.
Fit & Features
- Tropical print, mesh fabric, sewn-in knit lining
- Tube strapless neckline, non-slip grip lining
- Side zipper and hook-eye closure
- Lace-up back placket
- Flexible boning inserts
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000555
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Vintage Coded Two Pack Bangle Bracelets
This two-pack bangle bracelet set gives effortless summer energy like you just got back from somewhere coastal with too many photos to post.
Fit & Features
- Two-pack bangle bracelet set
- Chunky design
Style Number/Barcode: 07003-000329
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Maryanne Floral A-Line Formal Dress
Special Occasion
The Maryanna A-line dress brings effortless drama with every step. This satin column gown features an oversized floral print, a sleek halter neckline with hardware detail, and an open-back silhouette that's striking and bold.
Fit & Features
- Statement floral print, premium satin fabric, stretch knit lining
- Halter neckline with hardware insert, tie strap
- Open tie-back, lower zipper and hook-eye closure
- A-line floor-length silhouette
- Runs true to size
Where to Wear:
Outdoor weddings, vacations, honeymoons, resorts, cocktail parties, birthday dinners, milestone celebrations, summer date nights
Style Number/Barcode: 05002-000961
Category Name: Vacation Looks
Price: $29.97 $74.90
On Sale: Yes
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
Product Badge:- Sale
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Oceanside Kiss Open Back Midi Dress
This halter midi dress hugs in all the right places with a plunging neckline, ruched waist, and open back made for dinners, vacations, and every occasion that calls for extra attention.
Fit & Features
- Floral print, knit stretchy fabric, lined
- Plunge halter neckline, tie strap
- Open back
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-001130
Category Name: Vacation Looks
Price: $20.97 $45.90
On Sale: Yes
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
Product Badge:- Sale
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Island Attention Floral Tube Mini Dress
Booked the trip just to wear this dress. The bold tropical floral print and bodycon silhouette will make heads turn at the beach clubs, island resort, or a weekend pool party!
Fit & Features
- Statement floral print, knit-lined stretchy fabric
- Strapless tube neckline
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000751
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
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Cherry On Top Eyelet Romper
Caught flirting with the dress code again. This eyelet romper brings the charm with puff sleeves, a cinched fit, and the kind of open back detail that gets a second look at brunch, birthdays, and vacations.
Fit & Features
- Eyelet woven fabric, sewn-in woven lining
- Sweetheart neckline, tie bust, padded bra cups
- Short puff sleeves
- Open back, lower zipper and hook-eye closure
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06303-000049
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Postcards And Plans Satin Mini Dress
Serving vacation looks. The silky print dress boasts an open back detail, making this dress feel straight out of a suitcase packed for a European trip or sunny getaway.
Fit & Features
- Multi-print design, silky satin fabric, woven lining
- Strapless tube neckline, non-slip grip lining
- Side zipper and hook-eye closure
- Cutout open back detail with hook closure strap
- Curve-hugging fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001070
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M
Product Badge:- Sale
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Weekend In Soho Round Sunglasses
These sunglasses give every outfit a stylish finish. The slim, rounded rectangle shape and tortoise finish give off cool café in the city energy.
Fit & Features
- Rounded rectangle shape
- Slim design
- Tortoise pattern
- Tinted lenses
Style Number/Barcode: 07008-000129
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free