Vacation Looks
Vacation outfits should feel as effortless as your out-of-office vibe. Think long floral dresses that move with the breeze, easy cover-ups for poolside lounging, and bold two-piece sets that pop in every photo. From beachy maxis that bring instant elegance to denim shorts that nail casual cool, each piece blends comfort with style so you never have to choose between the two. These looks are made for packing light, looking chic, and serving up Instagram-worthy vacation moments.
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Vacation Looks
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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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Paradise Bound Braided Striped Straw Tote Bag
Step off the plane into paradise carrying this must-have straw tote bag! It's designed with convenient top handles and a trendy multi-hued braided striped pattern.
Fit & Features
- Faux leather top handles
- Multi-hued braided stripe design
- Large square-shaped body
- Straw material
Style Number/Barcode: 07203-2116
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Hello Summer V-Cut Bikini Bottoms
Say hello to summer in these trendy bikini bottoms featuring a V-cut waist, scrunched detailing at the back, and a thong fit. Pair with the matching bikini top for a pool party.
Shop Matching Top: Hello Summer Triangle Bikini Top
Fit & Features
- Nylon-blend fabric, high stretch
- V-cut waist
- Scrunched back
- Thong fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000011
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simply Sophisticated Faux Leather Block Heels
Step into these faux leather block heels for a simply sophisticated look for any occasion! These almond-toe heels feature a comfortable block heel and a closed-ankle style. The adjustable ankle strap with buckle closure secures the style. Complete the look with a trendy handbag.
Fit & Features
- Block Heel
- Almond toe
- Closed ankle, adjustable ankle buckle strap
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4856
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Hello Summer Triangle Bikini Top
Say hello to summer in this trendy bikini top featuring triangle-shaped cups with removable padding and dual spaghetti strap ties that let you customize the style. Pair with the matching bikini bottoms for a pool party.
Shop Matching Bottoms: Hello Summer V-Cut Bikini Bottoms
Fit & Features
- Nylon-blend fabric, high stretch
- Triangle design
- Removable padding
- Dual tie-back halter straps
- Lower tie-back straps
- Runs true to size
Style Number/Barcode: 07104-000009
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: In Stock
Available Color: SLATE
Available Size: L
Product Badge:- Sale
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Oh-So-Cute Puff Sleeve Lace-Up Gingham Mini Dress
Oh-so-cute and sweet! This gingham mini dress is sure to charm at brunch and picnics. You'll have comfort and style, made from a gauze woven fabric boasting a cheery gingham print line with a stretchy knit. With puff sleeves and a V-neckline, this bodycon dress flatters your figure and adds a fun touch with its lace-up back. The mini-length hem and playful gingham print make it perfect for any spring-to-summer event. Complete the look in sandals and sunnies!
Fit & Features
- Gingham print, gauze woven fabric lined with stretchy knit
- V-neckline
- Lace-up, back zipper and hook-eye closure
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5438
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cool Girl Era Wedge Heels
Enter your cool girl era and style up these sleek faux leather wedge heels to elevate your fave 'fits. Pair with your everyday shoulder bag.
Fit & Features
- Wedge heel
- Faux leather material
- Open almond-shaped toe
- Wide toe strap
- Thin adjustable ankle and heel straps, buckle detail
- Cushioned insole
- Runs true to size
Style Number/Barcode: 07406-000007
Category Name: Vacation Looks
Price: $28.90
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Feelings Sleeveless Ditsy Floral Mini Dress
Give yourself a sweet feeling in this ditsy floral mesh mini dress perfect for spring and summer soirees! With a sweetheart neckline, padded bra cups, and adjustable spaghetti straps you;ll feel confident and comfortable. The side ruched seams accentuate your curves along the bodycon fit for a playful touch. Complete the look with a choker necklace.
Fit & Features
- Ditsy floral print, mesh fabric, sewn-in knit lining, stretchy
- Adjustable spaghetti straps
- Sweetheart neckline, padded bra cups
- Back zipper and hook-eye closure
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5550
Category Name: Vacation Looks
Price: $9.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Spice Corset Lace-Up Floral Midi Dress
Sweet and spice combine on this floral midi dress designed with a stylish lace-up back, corset bodice, and a flirty front slit for movement. Complete the look with mules.
Fit & Features
- Ditsy floral print, smooth woven fabric, woven lining
- Sleeveless sweetheart neckline with tie
- Shoulder straps, side zipper and hook-eye closure
- Lace-up back design
- Underwire bust, corset bodice
- Front slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-3819
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Delicate Essence Puff Sleeve Corset Lace Mini Dress
The delicate essence of this lace mini dress will have you looking so cute at a bridal shower, as the birthday girl or graduate! Featuring sheer puff sleeves, an underwire bust for support, and flexible boning for a flattering bodycon fit. The front ruched seam adds a touch of sophistication to this playful mini-length dress. Complete the look in cute sandals and a purse!
Fit & Features
- Lace fabric lined with stretchy knit
- Back zipper and hook-eye closure
- Sweetheart neckline, underwire bust
- Flexible boning
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3226
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirt And Twirl Puff Sleeve Tie-Back Skater Dress
Flirt and twirl in this cute skater dress at parties and day dates! The puff short sleeves and square neckline add a touch of charm, while the tie-back design and skater silhouette create a flattering fit. Complete the look with hoop earrings.
Fit & Features
- Crepe woven fabric, stretchy knit lining
- Square neckline
- Tie-back detail
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3243
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casually Sultry Strapless Bodycon Midi Dress
Strut looking casually sultry in this strapless midi dress that accentuates your curves and can easily be dressed up or down!
Fit & Features
- Brushed knit double-lined stretchy knit fabric
- Strapless neckline
- Side ruched seams
- Bodycon silhouette
- Midi-length hem, side slit
- Runs true to size
Style Number/Barcode: 05102-000245
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: RED, BROWN
Available Size: XS, S, M, L
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Love's In The Air Floral Chiffon A-Line Dress
Slip into romance! This dainty floral chiffon short dress features a sweetheart neckline and bust tie to accentuate your figure while the wide shoulder straps and underwire bust provide support. The corset-trim bodice and back lace-up design add a touch of romance along the flattering A-line silhouette and short-length hem. Complete the look with a ring set and sandals for a date or brunch!
Fit & Features
- Sleeveless sweetheart neckline
- Wide shoulder straps
- Underwire bust, tie front, side zipper and hook-eye closure
- Corset-trim bodice, lace-up back design
- A-line silhouette, short-length hem
- Dainty floral print, chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-3007
Category Name: Vacation Looks
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fresh Vibe High-Rise Destructed Straight-Leg Jeans by Windsor Denim
These trendy destructed straight-leg jeans by Windsor Denim will give you that fresh vibe you crave for the summer season. Made with a stretchy cotton-blend denim fabric, they feature a high-rise waist and a straight-leg fit with destructed detailing for an effortlessly cool look. Include a five-pocket and belt loop design with a front button and hidden zipper closure. Style these jeans with a graphic tee and ankle booties.
Fit & Features
- Cotton-blend denim fabric with moderate stretch
- High-rise waist
- Straight-leg fit
- Destructed detailing
- Five-pocket and belt loop design
- Front button, zipper closure
- Runs true to size
Style Number/Barcode: 06602-0492
Category Name: Vacation Looks
Price: $6.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Moves Plunging Halter Bodycon Mini Dress
Make sultry moves with all eyes on you in this sexy bodycon mini dress your next night out! The slinky knit fabric offers plenty of stretch for that perfect comfortable fit. The mini-length dress is shaped with a sleeveless plunging V-neckline with a halter strap design, an open back for even more allure, lower back ruching to accentuate your curves, and a bodycon silhouette to flaunt your gorgeous figure. Style with a rhinestone lariat necklace and stiletto heels.
Fit & Features
- Stretchy knit fabric, knit lining
- Plunging V-neckline
- Halter straps
- Open back
- Back ruching
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5784
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: In Stock
Available Color: ROYAL
Available Size: L
Product Badge:- Sale
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Sunshine Weather Floral Chiffon Romper
Bare your shoulders on sun-soaked days in this floral chiffon romper at brunch, parties, or shower celebrations! Designed with flattering drop waist seam to accentuate your figure and a flowy short hem.
Fit & Features
- Floral print, chiffon fabric, sewn-in knit lining
- Strapless neckline
- Stretchy smocked bodice
- Drop waist seam
- Flowy short hem
- Runs true to size
Style Number/Barcode: 06403-1101
Category Name: Vacation Looks
Price: $9.97 $56.90
On Sale: Yes
Availability: In Stock
Available Color: NATURAL
Available Size: S, M, L
Product Badge:- Sale
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Easy And Breezy Lace-Up Midi Dress With Pockets
So effortlessly breezy for any plans, this A-line midi dress will turn heads with a lace-up bust and back detail, while the hidden side pockets are perfect for stashing your phone or lip gloss in.
Fit & Features
- Poplin woven fabric, woven lining
- Sweetheart neckline, lace-up front, stretchy smocked bust
- Spaghetti straps
- Lace-up back, lower zipper and hook-eye closure
- Drop waist seam, hidden side pockets
- A-line silhouette, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6023
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tropical Fun Rhinestone Pineapple Stud Earrings
Add a touch of tropical fun to your look with these juicy, cute pineapple stud earrings embellished with sparkling rhinestones.
Fit & Features
- Pineapples
- Rhinestone embellished
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000057
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Crush Marble Print Maxi Dress
They'll totally be crushing on you in this alluring abstract marble print maxi dress! It features a strapless straight-across neckline, ruching down one side seam with an adjustable drawstring, a sultry high-cut side slit, and an asymmetric maxi-length hem. The fitted bodice leads to a flowy silhouette. The marble-printed sheer mesh fabric includes a mini-length knit lining. Style with gemstone earrings.
Fit & Features
- Strapless straight-across elastic-banded neckline
- Ruching down one side seam, adjustable drawstring
- High-cut side slit, asymmetric maxi-length hem, lettuce-edge trim
- Fitted bodice, flowy silhouette
- Abstract marble print
- Sheer mesh fabric, mini-length knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5276
Category Name: Vacation Looks
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Three Way Tie Layered Bead Necklace
This layered necklace will win your heart! This stunning necklace features one beaded layer, one dainty beaded chain layer accented with mini clear stones, and one paperclip chain layer, creating a unique and versatile piece. Complete the look in a cute midi dress for a party!
Fit & Features
- Three-row layered design
- One beaded layer
- One beaded chain layer with mini clear stones
- One paperclip chain layer
- Lobster clasp closure
Style Number/Barcode: 07002-1879
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Raise The Bar Wide-Leg Jumpsuit
Raise the bar and strut in this sleeveless jumpsuit featuring a statement design with a plunge halter neckline and an alluring open back. Complete the look with earrings.
Fit & Features
- Smooth knit fabric, plenty of stretch
- Plunging sleeveless halter neckline
- Halter neck ties
- Open back
- Wide-leg silhouette
- Jumpsuit in size small is 58" shoulder to hem with a 13" front rise and a 30" inseam
- Runs true to size
Style Number/Barcode: 06502-2551
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Divine Cutie Tie-Back Ruffled Skater Dress
You'll look positively cute and divine in this short skater dress at brunch or graduations! Designed with a flattering square neckline, adjustable spaghetti straps for the perfect fit, and a tie-back design, this dress is perfect for every girlie. The skater silhouette and ruffled layer add a playful touch, while the short-length hem offers comfort and versatility. Complete the look in strappy mules.
Fit & Features
- Airy woven fabric, sewn-in knit lining
- Adjustable spaghetti straps
- Ruffled
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5733
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Immense Charm Six-Pack Earrings Set
Adding these six-pack earrings to your favorite looks will make it immensely more charming! The set features one pair of chain hoops, one pair of twist hoops, one pair of heart charm hoops, one pair of heart stud earrings, one pair of rhinestone cluster stud earrings, and one pair of faux pearl stud earrings. Complete the look with sandals.
Fit & Features
- Six-pack earrings set
- One pair of chain hoop earrings, post-back closure
- One pair of twist hoop earrings, post-back closure
- One pair of heart charm hoop earrings, post-back closure
- One pair of faux pearl studs, post-back closure
- One pair of rhinestone cluster studs, post-back closure
- One pair of heart studs, post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2067
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Absolute Charm Pleated Lace Trim Mini Skirt
Stroll like an absolute charmer in this ponte pleated mini skirt with a flirty eyelet lace trim that elevates your look!
Fit & Features
- Ponte knit fabric, stretchy knit shorts lining
- High-rise waist
- Side zipper and hook-eye closure
- Pleated silhouette
- Eyelet lace trim mini-length hem
- Runs true to size
Style Number/Barcode: 06503-1259
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: M, L
Product Badge:- Sale
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Enchanting Look V-Neck Button Down Skater Dress
Your day just got sweeter in this sleeveless skater dress perfect for spring and summer occasions! This V-neck skater dress boasts adjustable spaghetti straps and button closures that allow for the perfect fit while the skater silhouette and short-length hem elevate your style. Complete the look with sandals and sunnies!
Fit & Features
- Woven fabric with lining, no stretch
- Adjustable spaghetti straps
- V-Neckline
- Button down front
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5555
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale