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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Carry On Top Handle Linen Bag
Carry your must-haves in this cute linen bag with a top handle and detachable strap for multiple styling options.
Fit & Features
- Top handle
- Front flap with snap-lock closure
- Detachable strap
- Spacious interior with pocket
- Linen material
Style Number/Barcode: 07203-2128
Category Name: Vacation Looks
Price: $12.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Weekend Chic Sleeveless Midi Dress
Elevate your weekend look with this sleeveless midi dress with a sleek boat neckline, flirty low-cut back, and a flattering flowy silhouette. Dress it up with strappy sandals!
Fit & Features
- Woven fabric
- Boat neckline
- Low-cut back
- Drop waist seam
- Flowy silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000164
Category Name: Vacation Looks
Price: $19.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Beauty Rhinestone And Pearl Flower Earrings
You'll be a chic beauty in these stunning statement earrings featuring a flower petal design and cascading rhinestone and faux pearl accents.
Fit & Features
- Flower petal design
- Hanging rhinestone and faux pearl accents
- Fish hook closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000026
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Country Cutie Beaded Cowboy Hat
Top off your 'fits with the cutest cowboy hat featuring a straw woven material with a trendy ombre design and a beaded band with a tie-back closure.
Fit & Features
- Straw woven material, ombre design
- Structured top
- Wide curved brim
- Faux leather braided beaded band, tie-back closure
Style Number/Barcode: 07302-000074
Category Name: Vacation Looks
Price: $3.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Glamour Faux Pearl Belly Chain
This layered belly chain adds a touch of elegance and sophistication to any outfit, perfect for highlighting your waist with subtle shimmer from dainty faux pearls and rhinestones.
Fit & Features
- Layered chain design
- Rhinestones
- Faux pearls
- Lobster clasp closure
Style Number/Barcode: 07002-000019
Category Name: Vacation Looks
Price: $2.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Daydream Date Bow-Front Skater Dress
Giving total daydream vibes with a flirty twist. The bow-front detail and breezy skater silhouette make this short dress perfect for brunch, strolls, or spontaneous golden-hour photo ops.
Fit & Features
- Satin woven fabric, scenic print
- Sleeveless V-neckline, bow-front detail
- Adjustable spaghetti straps, smocked back
- High-rise waist
- Short skater silhouette, striped hem
- Runs true to size
Style Number/Barcode: 05102-000306
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Seaside Beauty Concho Shell Stud Earrings
Crafted to showcase your natural beauty, these concho shell earrings add a touch of coastal elegance to any outfit!
Fit & Features
- Concho shell design
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000027
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keeping It Salty Crochet Handbag
Add a splash of fun to your outfit with this crochet handbag for beach days or vacation! This playful bag features a comfy top handle and a zipper closure that opens to a spacious interior perfect for stashing your essentials in.
Fit & Features
- Top handle
- Zipper closure
- Spacious interior
- Crochet material
Style Number/Barcode: 07203-000023
Category Name: Vacation Looks
Price: $13.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Slay All Day Paisley Mesh Maxi Dress
Look good from every angle—this paisley mesh dress understood the assignment. The halter square neckline and high side slit bring all the heat for a night out or glam rooftop vibes.
Fit & Features
- Paisley print, mesh-lined fabric, moderate stretch
- Halter square neckline with spaghetti straps
- Form-hugging silhouette
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6099
Category Name: Vacation Looks
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Instant Chic Small Oval Sunglasses
Chic with a glossy finish, these small frame oval-shaped sunglasses are perfect for slipping on when you want to elevate your 'fit with zero effort.
Fit & Features
- Small oval-shaped design
- Plastic frame
- Built-in nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000005
Category Name: Vacation Looks
Price: $3.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Crush Mesh A-Line Mini Dress
She’s cute, she’s confident, she’s totally crushing it. This mesh mini dress is bringing flirty energy with its fitted, flowy fit and head-turning abstract floral print. Snap a selfie and get all the compliments!
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Large abstract floral print
- Sleeveless cowl neckline
- Spaghetti straps
- Open cross-back strappy design, tie closure
- Mini-length hem, fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05103-000354
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sun And Spritz Tropical Cutout Maxi Dress
Just add sun and a spritz—this tropical print maxi is made for main character getaways. With side cutouts and breezy vibes, it’s giving effortlessly hot in every snap.
Fit & Features
- Lightweight woven fabric with tropical print, bust lining
- Square neck
- Cutout sides on the bodice
- Fitted bodice with trim detailing
- Bust tie, tank shoulder straps, back zipper and hook-eye closure
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000246
Category Name: Vacation Looks
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tropical Elegance Floral Stud Earrings
Add a touch of tropical paradise to your look with these eye-catching floral stud earrings.
Fit & Features
- Tropical floral design
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000041
Category Name: Vacation Looks
Price: $2.97 $7.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Airy Aura Butterfly Arm Cuff
Delicate but daring. This butterfly arm cuff wraps your arm in airy elegance with a silhouette that flutters perfectly from brunch to beach to festival grounds.
Fit & Features
- Thin textured wrap-around design
- Cutout detailed butterfly accents
Style Number/Barcode: 07003-000054
Category Name: Vacation Looks
Price: $13.90
Availability: Out of Stock
Product Badge:- Ships Free
- Thin textured wrap-around design
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Merlot Nights Halter Maxi Dress
Rich, sultry, and unforgettable—this halter maxi dress stuns with a draped cowl neckline, curve-hugging fit, and open back detail that brings the drama for any formal affair. Complete the look with jewelry and stiletto heels.
Fit & Features
- Slinky knit stretch fabric
- Cowl halter neckline
- Open strappy back
- Curve-hugging silhouette
- Relaxed maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000632
Category Name: Vacation Looks
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wild Spirit Beaded Straw Cowboy Hat
This cowboy hat was made for sun-soaked adventures and music festival nights. The woven straw design keeps it breathable, while the bead and turquoise detail give it that effortlessly cool, free-spirited edge.
Fit & Features
- Beaded colored trim, back string bow design
- Curved wide brim
- Straw material
Style Number/Barcode: 07302-000075
Category Name: Vacation Looks
Price: $3.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Midnight Mirage Mesh Strapless Maxi Dress
All eyes on you. This strapless maxi dress features a ruched bust and hip detail with a sheer mesh skirt that flows for maximum drama. Finished with a gold accent at the neckline, it’s pure allure.
Fit & Features
- Partially lined sheer mesh fabric
- Strapless sweetheart neckline, hardware trim
- Curve-hugging sheer silhouette
- Sheer flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05103-000541
Category Name: Vacation Looks
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Goddess Energy Floral Mesh Ruffle Mini Dress
Giving goddess energy only. This floral mesh mini dress drapes effortlessly with a flirty ruffle hem and statement faux pearl beaded embellishment that hits just right. Perfect for an alluring night out or that sunset soirée you’ve been waiting for.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Abstract floral print
- Sleeveless plunging V-neckline, tie-back halter straps, partially open back
- Center faux pearl, beaded, and sequin embellished applique
- Asymmetric mini-length hem, ruffle trim, cascading ruffle accent
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-000434
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ocean Bloom Halter Mini Dress
Meet your next weekend obsession. This floral halter mini dress brings vacation energy anywhere you wear it, with its draped halter cowl neckline, open tie back, and flowy fit. Perfect for rooftop brunches, date nights, or celebrations.
Fit & Features
- Floral print, colored rhinestone embellishments
- Chiffon fabric lined with chiffon
- Cowl halter neckline
- Dual open tie-back design
- Side zipper and hook-eye closure
- A-line fit, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000316
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE
Available Size: XS
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Wild Intentions Zebra Velvet Maxi Dress
A little wild, a lot unforgettable. This burnout zebra velvet mesh maxi brings high-drama energy with its one-shoulder neckline, side cutout, and ruched bungee drawstring that lets you play with the slit height. Equal parts sleek and scandalous—just how we like it.
Fit & Features
- Zebra burnout velvet pattern, mesh fabric, sewn-in mesh lining
- One-shoulder neckline, bungee spaghetti strap
- Strappy back, bodice side cutout
- High front slit and ruched drawstring bungee cord
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000757
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Poised to Strike Maxi Dress
Designed to steal every glance in the room. This snake print mermaid dress serves full glam energy with its sculpted high neckline, luxe gold ball accents, and curve-hugging silhouette. Sleek, sultry, and unapologetically extra—just how you like it.
Fit & Features
- Snake print, smooth knit stretch fabric
- High neckline
- Gold ball hardware insets
- Mermaid, curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000756
Category Name: Vacation Looks
Price: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Petal Noir Floral Chiffon Maxi Dress
This halter maxi dress stuns with a draped cowl neckline, bold floral print, and a daring open back that leaves a lasting impression. Flowing and form-flattering, it’s your go-to for romantic date nights and elevated occasions.
Fit & Features
- Floral print, chiffon-lined fabric
- Halter cowl neckline
- Open back design, zipper and hook-eye closure
- Curve-hugging silhouette
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000577
Category Name: Vacation Looks
Price: $56.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L, XL
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Sultry Motion Mesh Halter Midi Dress
This mesh halter midi dress stuns with a plunging cowl neckline, bold bodice cutouts, and a high ruffled slit made for movement. With its curve-hugging fit and sheer allure, it’s the perfect mix of flirty, fierce, and unforgettable.
Fit & Features
- Mesh-lined fabric, moderate stretch
- Cowl halter neckline, hoop inserts, tie closure
- Open back
- Side cutout bodice, high front ruffled slit
- Form-hugging fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05103-000499
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
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Untamed Bloom Tie-Front Crop Top
Flirty, fearless, and just the right amount of wild. This top blends bold floral and animal prints for that effortlessly sultry vibe. The tie-front top and flirty flowy hem bring all the movement and attitude—no accessories required (but gold jewelry helps).
Shop The Matching Skirt: Untamed Bloom High-rise Slit Midi Skirt
Fit & Features
- Floral and animal print, mesh fabric, bust lining
- V-neckline with tie-front detail
- Sheer fitted long sleeves
- Flowy crop hem
- Runs true to size
Style Number/Barcode: 06202-000065
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: LEOPARD
Available Size: XS, S, M
Product Badge:- Part of a Set