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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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: $84.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free
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Miss Me Yet Abstract Babydoll Mini Dress
Serving just enough cuteness with every step. This abstract print chiffon babydoll dress features a plunge V-neckline with studded trim and an open back that practically guarantees compliments before you even make it to dinner.
Fit & Features
- Abstract print, chiffon fabric, smooth woven lining
- Plunge V-neckline with a studded trim bust
- Open back, adjustable spaghetti straps
- Babydoll mini-length silhouette, hanky hem
- Runs true to size
Style Number/Barcode: 05103-000851
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: GRAY
Available Size: XS, S, M, L
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Love Letters Ruffle Maxi Dress
Floaty dresses just do something to the mood. This floral chiffon maxi dress features a ruffle V-neck, low back detail, and tiered ruffles that move perfectly from vacation dinners to wedding guest season.
Fit & Features
- Floral print, chiffon fabric, woven lining with slit accent
- Ruffled trim V-neckline
- Adjustable spaghetti straps
- Low-cut back
- Side zipper and hook-eye closure
- Tiered ruffled maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-001482
Category Name: Vacation Looks
Price: $64.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
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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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Vacation Goddess Gemstone Stiletto Heels
These gemstone gladiator stiletto heels were made for sunset dinners, cocktails, and compliments from strangers. The barely there straps and colorful gem details give every outfit that “wait… where’d you get those?” effect.
Fit & Features
- 3" Stiletto heel
- Round toe
- Colored gemstone embellished gladiator straps
- Adjustable buckle closures
- Cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-000643
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: TAN
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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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: $34.90
Availability: In Stock
Available Color: RED
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Cutest Charm Striped Crochet Halter Top
Serving retro flirtiness and the cutest charm. This striped crochet halter top hugs just right and was made for rooftop hangs, concert nights, and spontaneous photo dumps. Style with the matching maxi skirt.
Shop Matching Bottoms: Cutest Charm Striped Crochet Maxi Skirt
Fit & Features
- Striped crochet knit fabric, moderate stretch
- Sleeveless halter neckline, tie-back spaghetti straps
- Cropped hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-000335
Category Name: Vacation Looks
Price: $22.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Cutest Charm Striped Crochet Maxi Skirt
Serving retro flirtiness and the cutest charm. This striped crochet maxi skirt hugs just right and was made for rooftop hangs, concert nights, and spontaneous photo dumps. Style with the matching crop top.
Shop Matching Top: Cutest Charm Striped Crochet Halter Top
Fit & Features
- Striped crochet knit fabric
- High-rise waist
- Maxi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06501-000123
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Beach Club Behavior Crochet Top
The kind of top that makes denim shorts feel way more intentional. This beaded crochet top layers over bikinis, bralettes, or nothing but confidence for vacations, beach days, or concerts.
Fit & Features
- Sheer crochet fabric
- Beaded embellished design
- Sleeveless crew neckline
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06005-000328
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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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: In Stock
Available Color: RED, MULTI
Available Size: 5.5, 6, 6.5, 7, 8, 7.5, 9, 10
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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, 6.5, 7, 7.5, 8, 8.5, 9, 10
Product Badge:- New Arrival
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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
- 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: $36.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Vacay Ready Halter Mesh Romper
Booked the trip just to wear this. This tropical floral halter mesh romper drapes effortlessly, with a strappy open back and a cascading ruffle sash that moves with you.
Fit & Features
- Tropical floral print, mesh fabric, built-in shorts lining
- Halter cowl neck, tie straps
- Open strappy tie-back
- Tiered ruffled hem with flower inset, cascading ruffle sash
- Runs true to size
Style Number/Barcode: 06503-000269
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: FUCHSIA
Available Size: S, M, L
Product Badge:- Best Seller
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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
- 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: XS, S, M, L
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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, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
Product Badge:- New Arrival
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Mint To Be Bangle Bracelet Set
Your stack just found its favorite trio. This bangle bracelet set mixes glossy resin with sleek metal for that effortless vibe with your look.
Fit & Features
- Three-pack bangle bracelet set
- Sleek metal bangles
- Resin square-shaped bangle
Style Number/Barcode: 07003-000233
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival
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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: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Salty Glam Puka Shell Necklace
Beachy, sparkly, and a little extra, just how we like it. This chunky puka shell necklace brings the shine with rhinestone embellishments that instantly dresses up your look.
Fit & Features
- Puca shell chain with rhinestone embellishments
- Chunky design
- Statement teardrop rhinestone charm
- Lobster clasp closure
Style Number/Barcode: 07002-000509
Category Name: Vacation Looks
Price: $19.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival
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Melissa Crochet Floral Formal Dress
Special Occasion
The Melissa crochet mermaid gown brings effortless glamour with every step. The plunging halter neckline, floral applique insets, and open tie back create a striking silhouette that brings a coastal allure to every occasion.
Fit & Features
- Crochet texture woven fabric, sheer mesh lining
- Plunge halter neckline, tie straps, beaded accents
- Open tie-back design, zipper and hook-eye closure
- Mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Bridal celebrations, beach weddings, destination weddings, coastal formals, engagement parties, vacations, honeymoons, bridal showers, birthday dinners, celebrations
Style Number/Barcode: 05002-001395
Category Name: Vacation Looks
Price: $89.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L, XL
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: $69.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L, XL
Product Badge:- New Arrival
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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, S, M, L
Product Badge:- New Arrival
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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: In Stock
Available Color: GREEN
Available Size: NS
Product Badge:- New Arrival