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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RSVP To Romance Floral Maxi Dress
The dress that somehow makes every plan feel worth showing up for. This floral flutter sleeve maxi dress pairs delicate ruffle details with a figure-skimming fit that's ready for bridal showers, brunch reservations, and every pretty occasion in between.
Fit & Features
- Mesh fabric with full-length lining
- Floral print
- Sweetheart neckline, ruched bust, tie detail
- Ruffled trim, short ruffled flutter sleeves
- Back zipper closure
- Maxi-length hem, form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-001265
Category Name: Vacation Looks
Price: $38.00 $52.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
Product Badge:- Sale
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Sunlit Shine Stone Thong Sandals
Minimal effort, maximum polish—these sandals are your throw-on-and-go kind of cute. Designed with stone embellishments and a sleek thong silhouette, they instantly elevate your vacation or weekend look.
Fit & Features
- Square toe
- Colored stone-embellishments, thong strap
- Cushioned insole
- Flat sole
- Metallic faux leather material
- Runs true to size
Style Number/Barcode: 07404-000069
Category Name: Vacation Looks
Price: $22.90
Availability: Out of Stock
Product Badge:- Ships Free
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Flirting In Positano A-Line Mini Dress
Meet the dress equivalent of booking the flight before asking questions. With its dreamy coastal print and easy strapless fit, this mini dress was made for European getaways, brunch, and sunny day plans.
Fit & Features
- Multi-print design, linen-blend woven fabric, woven lining
- Strapless neckline, non-slip grip lining
- Side hidden zipper and hook-eye closure
- Bar back accent and cutout
- A-line fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000561
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: MULTI
Available Size: XS
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Sunday In Bloom Strapless Midi Dress
This midi dress feels like a soft yes to every pretty plan on your calendar. The delicate floral print, smocked bodice, and flowy silhouette make it perfect for vacations, brunch, or any sunny day plans.
Fit & Features
- Floral borderprint, cotton woven fabric, smooth woven lining
- Strapless smocked bodice with stretch
- Back zipper and hook-eye closure
- Flowy A-line silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000798
Category Name: Vacation Looks
Price: $51.00 $72.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE, PINK
Available Size: S, M, L
Product Badge:- Sale
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Cherry On Top Lace Mini Dress
Pretty, playful, and impossible to ignore. This lace mini dress brings all the flirty details with ruffle trim, a dainty bust tie, and a twirl-worthy fit that feels straight out of a summer romance scene.
Fit & Features
- Lace fabric
- Ruffled trim keyhole tie square neckline
- Ruffled trim shoulder straps
- Lace-up back design
- Ruffled trim and lace front panels
- A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001059
Category Name: Vacation Looks
Price: $24.97 $54.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: XXS, XS, S, M, L
Product Badge:- Sale
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Pretty Breeze Floral Strappy Midi Dress
This midi dress feels like golden hour in outfit form. The tiny floral print, gathered sweetheart neckline, and open tie-back detail bring that soft, romantic vibe that always looks good at showers, graduations, and brunch.
Fit & Features
- Ditsy floral print, woven fabric
- Sweetheart neckline, tie bust
- Spaghetti straps
- Strappy open tie-back design
- A-line silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-001383
Category Name: Vacation Looks
Price: $46.00 $64.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
Product Badge:- Sale
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Paisley Mood Chiffon Halter Top
Print with a little plot twist. This paisley chiffon halter top brings a cinched sweetheart neckline, open tie-back design, and flowy hanky hem for cute and trendy plans. Pair with the matching maxi skirt.
Shop Matching Bottoms: Paisley Mood Chiffon Maxi Skirt
Fit & Features
- Paisley printed chiffon fabric
- Sleeveless sweetheart neckline, center cinched bust design
- Tie-back halter spaghetti straps
- Open back, lower tie-back straps
- Mid-length hanky hem, flowy fit
- Runs true to size
Style Number/Barcode: 06003-000401
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Paisley Mood Chiffon Maxi Skirt
Print with a little plot twist. This paisley chiffon maxi skirt brings a mid-rise waist and long fitted silhouette for cute and trendy plans. Pair with the matching halter top.
Shop Matching Top: Paisley Mood Chiffon Halter Top
Fit & Features
- Paisley-printed chiffon fabric, mini-length lining
- Mid-rise waist
- Maxi-length hem
- Fitted silhouette
- Runs true to size
Style Number/Barcode: 06401-000052
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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In Your Good Graces Halter Mini Dress
Sweet, but make it a little unexpected. This halter mini skims your shape with a soft, textured feel and a lace trim hem that adds just enough detail for showers, graduations, or dressy brunch plans.
Fit & Features
- Textured chiffon fabric, sewn in knit stretchy lining
- High halter neckline with tie straps
- Open back
- Bodycon mini silhouette
- Lace trim hem
- Runs true to size
Style Number/Barcode: 05102-000794
Category Name: Vacation Looks
Price: $32.00 $44.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
Product Badge:- Sale
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Brunch Bound Espadrille Wedges
Elevating every outfit without even trying. These espadrille wedges pair braided textures with an easy platform silhouette, making them the pair you'll reach for from brunch dates to vacation plans.
Fit & Features
- Espadrille wedge heel
- Platform sole
- Open round toe
- Espadrille straps
- Dual straps across the foot, adjustable ankle strap with buckle closure
- Faux leather footbed
- Runs true to size
Style Number/Barcode: 07406-000070
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: NATURAL
Available Size: 6, 7, 8, 9, 10
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Pretty Girls Drink Matcha Tank Top
A little caffeine, a little flirting, and suddenly the outfit is complete. This tank top keeps things cute and effortless with a fitted crop silhouette that's made for matcha runs, errands, and spontaneous plans.
Fit & Features
- Soft stretchy knit fabric
- Sleeveless scoop neckline
- Tank shoulder straps
- "Pretty Girls Drink Matcha" front script
- Fitted crop-length hem
- Runs true to size
Style Number/Barcode: 06002-000692
Category Name: Vacation Looks
Price: $19.90
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
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Clear The Calendar Jelly Flats
Cute plans require cute steps. These jelly square toe flats bring an easy slip-on finish with a sheer look that works for day dates, weekend plans, and summer trips.
Fit & Features
- Square toe
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Slip-on sheer design
- Flat sole
- Jelly material
- Runs true to size
Style Number/Barcode: 07405-000034
Category Name: Vacation Looks
Price: $18.90
Availability: In Stock
Available Color: BLACK, CLEAR, BROWN
Available Size: 5, 6, 7, 8, 9, 10
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Butterfly Kisses Mesh Maxi Skirt
Floaty, flirty, and fully saved to the outfit inspo folder. This mesh butterfly print maxi skirt hugs just right and pairs perfectly with the matching top.
Shop Matching Top: Butterfly Kisses Mesh Tie-Front Top
Fit & Features
- Butterfly print, mesh fabric, bust lining
- Long sleeves with flared cuffs
- Tie-front neckline
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06501-000124
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: TAUPE
Available Size: XS, S, M, L
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Lowkey Bold Strapless Ruffle Hem Mini Dress
Not here to blend in—this one hugs, shapes, and makes an impression without trying. The strapless bodycon mini dress with a ruffle hem and sheer waist detail brings texture and dimension that feels just as good as it looks.
Fit & Features
- Textured knit fabric with partial knit lining, moderate stretch
- Strapless straight-across neckline
- Sheer waist insert
- Mini-length tiered ruffled hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000305
Category Name: Vacation Looks
Price: $19.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: S, L
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Golden Hour Crochet Halter Dress
Booked for golden hour and not coming back early. This crochet halter mini dress features floral appliqué and a lace-up back that keeps things effortlessly pretty with just enough detail to stand out.
Fit & Features
- Crochet texture-lined knit fabric
- Halter plunge neckline with beaded strap
- Open back with lace-up design
- Floral applique
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000605
Category Name: Vacation Looks
Price: $23.97 $52.90
On Sale: Yes
Availability: In Stock
Available Color: NATURAL
Available Size: XS
Product Badge:- Sale
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Style Upgrade Blue Light Glasses
Your screen time just got a style upgrade. These square blue light glasses keep things sharp while helping filter blue light, perfect for work days, study sessions, and late-night scrolling.
Fit & Features
- Square-shaped plastic frame
- Built-in nose pads
- Clear blue-light lenses
Style Number/Barcode: 07008-000113
Category Name: Vacation Looks
Price: $11.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
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Stack It Up Five-Pack Ring Set
Caught in your accessorizing era. This five-pack ring set brings all the chunky designs and stone embellishments you need to switch up your vibe from casual coffee runs to last-minute plans.
Fit & Features
- Five-pack ring set
- Multiple chunky designs
- Stone embellishments
Style Number/Barcode: 07004-000125
Category Name: Vacation Looks
Price: $16.90
Availability: In Stock
Available Color: PINK
Available Size: 7, 8
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Coffee First Oval Sunglasses
The sunglasses you'll keep reaching for. These sleek oval sunglasses bring an effortless, wear-with-everything vibe that works for coffee runs, weekend plans, and everything in between.
Fit & Features
- Oval shaped silhouette
- Tinted lenses
- 100% UV protection
- Metal arms with plastic trim
Style Number/Barcode: 07008-000167
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
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Simply Sweet Ruffle Skater Dress
Consider this your excuse to romanticize even the simplest plans. The ruffle skater dress hugs up top with a soft stretch fit, then flows into that twirl-ready skirt made for brunch dates, parties, and everything in between.
Fit & Features
- Smooth knit fabric, high stretch
- Sleeveless V-neckline, ruched bust
- Adjustable spaghetti straps
- V-shaped drop waist seam
- Asymmetric tiered ruffled design
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05101-001227
Category Name: Vacation Looks
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
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Perfectly Styled Pearl Charm Layered Necklace
Tiny detail, instant outfit upgrade. This pearl charm layered necklace mixes a sleek herringbone chain with a dainty textured chain for that perfectly styled finish.
Fit & Features
- Two-row layered design
- Herringbone chain
- Dainty textured chain, faux pearl charm
- Lobster clasp closure with extender
Style Number/Barcode: 07002-000475
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Desert After Dark Fringe Shoulder Bag
Add western drama with this faux suede shoulder bag that brings movement and attitude to every outfit. The adjustable belted strap with stud accents and fringe tassel charms makes it perfect for festivals, concerts, or adding flair to everyday looks.
Fit & Features
- Faux suede material
- Adjustable western-inspired belted shoulder strap, stud accents
- Fringe tassel charms
- Top zipper closure
- Spacious lined interior with an open pocket
Style Number/Barcode: 07203-000197
Category Name: Vacation Looks
Price: $30.90
Availability: In Stock
Available Color: CAMEL
Available Size: NS
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Sleek Attitude Oval Sunglasses
Serving sleek attitude with every glance. These oval sunglasses bring a chic, lightweight feel with just enough edge for everyday plans, from coffee runs to last-minute invites.
Fit & Features
- Oval-shaped design
- Thin metal arms, metal side accents
- Thin metal nose bridge
- Adjustable rubber nose pads
- Lightly tinted lenses
Style Number/Barcode: 07008-000248
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BLUE
Available Size: NS
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Petal Poise Floral Earrings
Romance, but make it gallery-worthy. These floral earrings bring sculpted petal accents and glossy polish for weddings, dressy dinners, and outfits that need a polished little flourish.
Fit & Features
- Glossy marble sculpted petal accents
- Polished trim
- Statement floral silhouette
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000448
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Caught Looking Rectangle Sunglasses
Serving quiet luxury with a little attitude. These retro-inspired rectangle sunglasses are the kind you throw on when the outfit needs one last detail that says “yeah, I planned this.”
Fit & Features
- Lightweight plastic frame construction
- Structured rectangle silhouette
- Tinted lenses with a sleek finish
- Thin side arms with a vintage-inspired feel
- 100% UV protection
Style Number/Barcode: 07008-000227
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: TORTOISE
Available Size: NS