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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Soft Sculpt A-Line Mini Tube Dress
Fit & Features
- Smooth knit fabric with knit lining, high stretch
- Strapless straight-across neckline
- Open cross-back strappy design
- Ruched detailing
- Mini-length hem
- Fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05103-000872
Category Name: Vacation Looks
Price: $38.90
Availability: In Stock
Available Color: WHITE
Available Size: L
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Talk Of The Town Mesh Mini Dress
The kind of dress that makes mirror selfies mandatory. This off shoulder mini dress drapes in all the right places with a blouson fit and flowing sash detail that's polished and flirtatious.
Fit & Features
- Mesh fabric lined with stretchy knit
- One-shoulder neckline
- Attached sash accent
- Blouson relaxed bodice
- Fitted mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000943
Category Name: Vacation Looks
Price: $38.90
Availability: Out of Stock
Product Badge:- Ships Free
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Coastal Daydream Maxi Skirt
Floaty, effortless, and made for sunny vacations and weekend plans. This tiered maxi skirt brings an easy beach to brunch feel with a breezy silhouette that moves with you.
Fit & Features
- Airy woven fabric, short woven lining
- High-rise stretchy smocked tie waist
- Flowy tiered ruffled silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06301-000015
Category Name: Vacation Looks
Price: $16.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: L
Product Badge:- Sale
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Sleek Strike Square Sunglasses
Lowkey dangerous in the best way—these were made to add a little attitude. The sleek square sunglasses shape keeps it polished, while the snake-inspired arms wrap things up with just the right amount of edge.
Fit & Features
- Square-shaped design
- Tortoisehell arms with snake design
- Thin metal nose bridge
- Adjustable rubber nose pads
- Tinted lenses, small studded side details
- 100% UV protection
Style Number/Barcode: 07008-000244
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: TORTOISE
Available Size: NS
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Just Add Sandals Midi Skirt
The outfit came together the second this skirt showed up. A hanky midi skirt with a ruched mid-rise waistband and flowy A-line fit, it's the effortless piece that works for brunch, vacations, and every plan in between.
Fit & Features
- Smooth knit fabric, knit lining, high stretch
- Mid-rise ruched waistband
- A-line flowy fit
- Hanky midi-length hem
- Runs true to size
Style Number/Barcode: 06501-000195
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BLUE
Available Size: L
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Easy Plans Button Romper
From vacation mornings or weekend plans, it's the romper you'll keep reaching for when you want to look effortlessly chic. This sleeveless romper serves polished allure with a tailored button-front bodice and breezy shorts that are ready for everything on your calendar.
Fit & Features
- Linen-like woven fabric
- Square neckline
- Wide shoulder straps
- Button front accents
- Flowy shorts hem
- Runs true to size
Style Number/Barcode: 06303-000059
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: NATURAL
Available Size: S, M, L
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Chic Upgrade Stone Hand Chain
Your bracelet stack just got a chic upgrade. This three-row hand chain connects from wrist to ring with stone and rhinestone embellishments for a glam finish that does all the accessorizing for you.
Fit & Features
- Hand chain silhouette connecting bracelet to ring
- Three-row design
- Stone and rhinestone embellishments
- Lobster clasp closure with extender
- Adjustable fit
Style Number/Barcode: 07003-000266
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Dahlia Sequin Knit Mermaid Dress
Special Occasion
Dressed-up plans get a sleek dose of shine with this floor-length silhouette. This sequin knit mermaid dress pairs a cowl neckline with halter ring trim and an open back for a polished occasion look. The mermaid shape keeps the finish long, refined, and striking from every angle.
Fit & Features
- Sequin knit fabric
- Cowl neckline
- Halter strap with ring trim
- Open back design
- Floor-length mermaid silhouette
- Runs true to size
Where to Wear:
Weddings, engagement parties, vacations, honeymoons, resort getaways, cocktail parties, special date nights, destination celebrations
Style Number/Barcode: 05002-001681
Category Name: Vacation Looks
Price: $69.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
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Lustrous Tie Back Cowl Neck Maxi Dress
A liquid-like shimmer finish gives this maxi dress a bold look with barely any effort. The softly draped neckline and adjustable back tie create a flattering, fluid fit made for dinner reservations, celebrations, and vacation plans.
Fit & Features
- Metallic shimmer printed chiffon fabric, stretch knit lining
- Cowl neckline
- Spaghetti straps
- Adjustable tie-back detail
- Body-hugging maxi fit, side slit accent
- Runs true to size
Style Number/Barcode: 05101-001406
Category Name: Vacation Looks
Price: $52.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Dressy Invite Flower Earrings
These floral earrings came dressed for the invite. Layered fabric petals, beaded accents, and faceted drops bring playful movement to dresses, matching sets, and special occasion looks.
Fit & Features
- Layered fabric floral design
- Beaded strand accents
- Faceted drop embellishments
- Linear statement silhouette
- Fish hook closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000474
Category Name: Vacation Looks
Price: $11.90
Availability: In Stock
Available Color: GREEN
Available Size: NS
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Seaside Selects Earring Set
Your jewelry lineup just booked a beach trip. This six-pair earring set mixes rhinestones, faux pearls, shells, and starfish designs for endless styling options from brunch to getaway plans.
Fit & Features
- Six-pair earrings set
- Rhinestones, faux pearls, shells, and starfish designs
- Various styles and silhouettes
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000377
Category Name: Vacation Looks
Price: $10.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- Best Seller
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Sunset Spritz Multi-Print Tube Top
Pool plans, brunch plans, “wait where are we going next?” plans. This multi-print tube top brings the flirty vibe with a strapless sweetheart neckline, ruched detailing, and a form-hugging fit. Pair with the matching mini skort.
Shop Matching Bottoms: Sunset Spritz Multi-Print Ruffle Mini Skort
Fit & Features
- Knit fabric, high stretch
- Floral and animal multi-print pattern
- Strapless sweetheart neckline, padded bra cups
- Ruched detailing
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000681
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Ava Tropical Beaded Mesh Mini Dress
Special Occasion
The Ava beaded mesh detail gives this mini its standout finish. This beaded mesh mini dress pairs a strapless neckline with a twisted bust detail and tropical motif for a statement look with texture and shine. The bodycon silhouette keeps the embellished design sleek and defined.
Fit & Features
- Tropical motif design, beaded embellishments
- Lined mesh fabric, minimal stretch
- Strapless neckline, non-slip grip lining
- Twisted bust detail
- Bodycon mini silhouette
- Runs true to size
Where to Wear:
Vacations, honeymoons, resort getaways, birthday parties, date nights
Style Number/Barcode: 05001-000933
Category Name: Vacation Looks
Price: $89.90
Availability: In Stock
Available Color: BLACK, PRINT
Available Size: XS, S, M, L
Product Badge:- Ships Free
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Escape Plan Tropical Satin Halter Maxi Dress
Vacation mode starts here. This tropical satin maxi dress pairs a draped cowl halter neckline with a curve-skimming silhouette and a lace-up open back for sunset dinners and destination plans.
Fit & Features
- Smooth satin woven fabric
- Draped cowl halter neckline
- Tropical palm leaf pattern
- Lace up open back with adjustable ties
- Maxi length hem
- Runs true to size
Style Number/Barcode: 05101-001302
Category Name: Vacation Looks
Price: $64.90
Availability: In Stock
Available Color: NATURAL
Available Size: S, M, L
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Striking Zebra Mesh Bodycon Mini Dress
Animal print is back in its boldest form. This mesh mini dress updates the trend with a curve-skimming fit, halter neckline, and ruffled hem for added movement. It’s made for nights when a minimal outfit is not the plan.
Fit & Features
- Zebra print, lined mesh fabric
- Halter V-neckline
- Curve-hugging fit
- Asymmetrical ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000795
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, M, L
Product Badge:- Best Seller
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Floral Moment Halter High Slit Maxi Dress
Fit & Features
- Floral printed mesh fabric with high stretch
- Sleeveless deep V-neckline
- Tie-back halter straps, open back
- Ruched front design
- Maxi-length asymmetric hem, high-cut front slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05101-001446
Category Name: Vacation Looks
Price: $46.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
- Floral printed mesh fabric with high stretch
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Wild Bloom Floral And Leopard Print Mini Dress
Romance met its wilder side. This floral and leopard print mini dress pairs a sculptural flower accent with a plunging halter neckline, open back, and ruffled hem for date nights and dressier plans.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Floral and leopard multi-print pattern
- Sleeveless plunging V-neckline, metal flower sculptural accent
- Tie-back halter straps, open back
- Mini-length ruffled hem, ruffled detail
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000398
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
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Gloss Pop Two-Pack Bracelet Set
This two-pack bangle bracelet set adds a glossy pop to vacation looks, brunch outfits, and every outfit that needs a quick accessory win.
Fit & Features
- Two-pack bangle bracelet set
- One marbled style bracelet
- One textured bracelet
- Smooth resin material
Style Number/Barcode: 07003-000294
Category Name: Vacation Looks
Price: $13.90
Availability: In Stock
Available Color: PINK
Available Size: NS
Product Badge:- New Arrival
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Too Cute To Cancel Floral Lace Crop Top
This lace halter top is doing all the flirting for you. With sheer embroidered details and an open tie back, it’s the kind of top that pairs perfectly with denim and casual plans.
Fit & Features
- Sheer floral lace woven fabric, bust lining
- Halter V-neckline, tie straps
- Open tie-back design
- Sheer scallop trim crop hem
- Runs true to size
Style Number/Barcode: 06003-000316
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: IVORY
Available Size: L
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Perfect Plus One Platform Mules
Your warm-weather plans just found their perfect plus-one. This raffia platform mules brings that effortless vacation energy with a chunky heel and a belted strap that adds trendy flair to any look.
Fit & Features
- Chunky block heel
- Square toe
- Wide strap with a belted accent
- Cushioned insole
- Raffia material
- Runs true to size
Style Number/Barcode: 07401-000632
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: NATURAL
Available Size: 7.5
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Easy Agenda Wide Leg Twill Pants
The polished pair that still knows how to keep things relaxed. These mid rise twill pants feature a clean fitted waist and fluid wide-leg silhouette perfect for pairing with sandals and plans.
Fit & Features
- Smooth twill woven fabric
- Mid-rise waist
- Back zipper closure
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06302-000023
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: BEIGE
Available Size: XS, S, M, L
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Switch It Up Lace Trim Asymmetrical Top
One top, multiple ways to make it yours. This asymmetrical top features a ruched tie front, convertible halter straps, and lace trim that brings just enough romance to denim jeans for weekend plans, vacations, and everyday styling.
Fit & Features
- Texture knit fabric, bust lining
- Convertible neck tie straps
- Side slit accent
- Asymmetrical lace trim hem
- Runs true to size
Style Number/Barcode: 06001-000608
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Boho Romance Vibes Long Sleeve Tie Front Top
This pointelle knit crop top features a tie-front closure, dreamy bell sleeves, and delicate open-knit detailing. Perfect layered over a bralette or styled solo for that effortlessly flirty look.
Fit & Features
- Pointelle knit fabric
- Bell long sleeves
- Scoop neckline
- Tie-front closure
- Ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06005-000024
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: IVORY
Available Size: S, L
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Dreamy Views Ahead Chiffon Dress
Soft layers, flutter sleeves, and the kind of fit that makes getting ready feel easy. This chiffon mini dress was made for showers, graduations, and birthday brunches!
Fit & Features
- Airy chiffon fabric, lined
- V-neckline
- Flutter short sleeves
- Tie-back design
- A-line, ruffled mini-length silhouette
- Runs true to size
Style Number/Barcode: 05101-000894
Category Name: Vacation Looks
Price: $22.97 $48.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE, BLUE
Available Size: XS, XXS, S, M, L
Product Badge:- Sale