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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Artsy Flair Strapless Cutout Abstract Mini Dress
Showcase an artsy flair in this abstract mesh mini dress tonight! Featuring a striking strapless neckline, side ruched seams for a flattering fit, and a unique side cutout design, this bodycon mini-length dress is all about highlighting your curvaceous figure. Complete the look with stiletto heels.
Fit & Features
- Abstract print, mesh fabric, stretchy knit lining
- Strapless neckline
- Side cutout
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5693
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sure To Love Floral Woven Puff-Sleeve Skater Dress
You'll love wearing this sweet floral puff-sleeve skater dress all summer long! The lightweight woven fabric is detailed with a soft floral print for a pretty feminine look. The short dress features a scoop neckline with ruching and a tie-front accent, short puff sleeves with elastic cinched hems, a stretchy smocked high waist, and an adorable fit-and-flare silhouette with a ruffled hem for a flirty vibe. Style with sneakers for a cute and casual outfit.
Fit & Features
- Floral print
- Woven fabric with smooth woven lining
- Ruched scoop neckline with tie-front detail
- Short puff sleeves with elastic cinched hems
- Stretchy smocked high waist
- Fit-and-flare silhouette, ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5716
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Serving Vibes Halter Crop Top
This halter crop top will serve major stunning vibes for cocktails and dinner! It is designed with ruched side seams and a fitted crop hem that accentuates your figure.
Fit & Features
- Sheen knit fabric, sewn-in knit lining, high stretch
- Halter plunge neckline with tie closure
- Side ruched seams
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000679
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: NAVY, RED, WINE, BROWN, BROWN-2, CHARTREUSE
Available Size: XS, S, M, L
Product Badge:- Back In Stock
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Garden Of Romance Tie Back Rose Floral A-Line Dress
Let your love bloom for this rose floral chiffon midi dress perfect for garden parties and weddings! Featuring a square neckline, adjustable spaghetti straps, and a tie-back for the perfect fit, this flowy A-line silhouette dress will have you feeling flirty and feminine. With a front slit and midi-length hem, it's perfect for styling with chic stiletto heels.
Fit & Features
- Rose floral print, chiffon fabric lined with stretchy knit
- Square neckline
- Adjustable spaghetti straps
- A-Line silhouette
- Front slit
- Runs true to size
Style Number/Barcode: 05101-3257
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Signature Stripes Strapless A-Line Maxi Dress
Show off your signature style in this striped maxi dress perfect for casual summer plans! Features a strapless neckline, a stretchy smocked bodice for a comfortable fit, and a flattering A-line midi silhouette with hidden side pockets to keep your hands warm. Complete the look with sunglasses and trendy sandals.
Fit & Features
- Striped pattern, cotton woven fabric, no stretch
- Strapless neckline
- Stretchy smocked bodice
- Hidden side pockets
- A-line midi silhouette
- Runs true to size
Style Number/Barcode: 05102-5802
Category Name: Vacation Looks
Price: $6.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Aesthetic Pairing Three-Pack Bracelet Set
Elevate any look with this three-pack bracelet set featuring a paperclip chain-link bracelet and two stretchy beaded bracelets. Complete the look with a cute crossbody bag for any occasion!
Fit & Features
- Three-pack bracelet set
- One paperclip chain-link bracelet, adjustable lobster clasp closure
- Two stretchy beaded bracelets
Style Number/Barcode: 07003-0561
Category Name: Vacation Looks
Price: $2.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Catch Attention Cowl Neck Abstract Floral Maxi Dress
Catch everyone's attention in this abstract floral maxi dress at cocktail hour! The cowl neckline adds a touch of sophistication while the adjustable spaghetti straps provide a perfect fit. The form-hugging silhouette flatters your figure and the maxi-length hem offers a chic finish. Complete the look with a clutch and heels.
Fit & Features
- Abstract floral print, mesh fabric lined with stretchy knit
- Cowl neckline
- Adjustable spaghetti straps
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05101-3323
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fluttering Elegance Rhinestone Butterfly Earrings
These charming earrings add a whimsical style to your look! They feature butterflies with mini rhinestone embellishments, linear chains with bar trim, and a post-back closure. Complete the look with a trendy denim jacket.
Fit & Features
- Butterflies with mini rhinestone embellishments
- Linear chains with bar trim
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2057
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Whimsical Appeal Puff Sleeve Chiffon Skater Dress
Swiss dots add whimsical appeal to this charming chiffon skater dress perfect for birthdays, graduations, or showers! With sheer puff sleeves, a sweetheart neckline, and a tiered ruffled skater silhouette, this dress is both playful and flattering. Its short-length hem adds a touch of flirty charm. Complete the look in mules and a trendy purse!
Fit & Features
- Swiss dot chiffon fabric lined with stretchy knit
- Back zipper and hook-eye closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-2999
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold Impact Toggle Chain Bracelet
Perfectly bold and trendy, this toggle chain bracelet adds something unique to every look!
Fit & Features
- Toggle closure
- Chunky chain link
Style Number/Barcode: 07003-0698
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Way She Moves Striped Midi Skirt
This striped midi skirt has entered the girl's vacay chat! Boasting a sexy bodycon silhouette and mid-rise waist, you'll be the hit of the trip. Pair with the matching top to complete the look!
Shop Matching Top: Way She Moves Striped Bra Top
Fit & Features
- Striped print, scalloped trim, stretchy knit fabric
- Mid-rise waist
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06401-0743
Category Name: Vacation Looks
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Style Bow Detail Polka Dot Mesh Mini Dress
Show off the sweetest style on summer dates in this bow detail polka dot mini dress! Designed with an airy sheer mesh fabric with a knit lining for coverage, this mini-length dress is accented with an adorable polka dot pattern for the cutest vibe. It features a sleeveless V-neck and back design with a dainty eyelet trim, tank shoulder straps, a mini bow detail at the bust for a sweet touch, tie-back spaghetti straps, and a flirty flowy A-line silhouette. Pair with strappy mules.
Fit & Features
- Polka dot printed sheer mesh fabric with knit lining
- Plenty of stretch
- V-neck and back, tank shoulder straps
- Mini bow detail, eyelet trim
- Tie-back straps
- A-line fit
- Runs true to size
Style Number/Barcode: 05102-5828
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Blooming Allure Floral Mesh High-Slit Maxi Skirt
Giving goddess vibes with a flirty twist. This floral mesh maxi skirt brings all the drama with its flowy fit and daring high-cut side slit.
Shop Matching Top: Blooming Allure Floral Mesh Cutout Tube Top
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Large floral print
- High-rise fitted waist
- High-cut side slit
- Maxi-length hem, flowy silhouette
- Flowy silhouette
- Runs true to size
Style Number/Barcode: 06501-000066
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Sheer mesh fabric with knit lining, high stretch
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A Little Wild One-Shoulder Zebra Print Maxi Dress
Your next night out just got a little wild in this sassy zebra print maxi dress perfect for vacation or the weekend! This form-hugging dress features a one-shoulder neckline and spaghetti strap, with a side drawstring cutout to show some skin. The high side slit and maxi-length hem add a flirty touch to this fierce and flattering piece. Complete the look with heeled sandals and earrings.
Fit & Features
- Zebra printed knit fabric, plenty of stretch
- One-shoulder neckline, spaghetti strap
- Side drawstring cutout
- High side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5821
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute Feels Off-The-Shoulder Sweater Mini Dress
Feel cute in this off-the-shoulder sweater mini dress all year round! The folded off-the-shoulder neckline adds a flirty touch, while the bodycon fit accentuates your curves perfect for a day or night on the town. Complete the look in block heels.
Fit & Features
- Sweater knit fabric, moderate stretch
- Off-the-shoulder neckline
- Bodycon fit
- Mini-length
- Runs true to size
Style Number/Barcode: 06005-1947
Category Name: Vacation Looks
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Darling Babe Floral Woven Puff Sleeve Skater Dress
Create a darling day date look with this floral puff sleeve skater dress! Made with a lightweight woven fabric, it is detailed with a charming dainty floral print for those sweet feminine vibes. The short dress features a V-neckline with a cute tie-front detail, short puff sleeves with a ruffled trim, a high waist seam, and a skater hem with a flirty fit-and-flare silhouette. Style with a dainty charm necklace and heels.
Fit & Features
- Dainty floral print
- Woven fabric
- V-neckline, tie-front detail
- Short puff sleeves, ruffled trims
- Back zipper closure, high waist seam
- Short skater skirt, fit-and-flare silhouette
- Runs true to size
Style Number/Barcode: 05101-3466
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Clear Obsession PVC Flat Sandals
You'll be obsessed with these flat sandals perfect for styling on rotation! They feature an almond toe, a clear PVC strap, and a flat sole with edge trim on faux leather material. Complete the look with a trendy crossbody purse.
Fit & Features
- Almond toe
- Clear PVC strap
- Flat sole with edge trim
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1233
Category Name: Vacation Looks
Price: $12.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfect Always Strapless Cutout Ruffle Maxi Dress
Have all eyes on you in this strapless maxi dress boasting a sweetheart twist neckline and a cutout bodice. The smooth knit fabric hugs your curves along the form-hugging silhouette and creates a front center ruffle design.
Fit & Features
- Smooth knit lined fabric, moderate stretch
- Strapless sweetheart twist neckline
- Cutout bodice
- Center front ruffle design
- Form-hugging, maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3601
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Looking Back Strapless Strappy Mini Dress
Make everyone look back at you in this sassy rib knit mini dress! Perfect for summer BBQs or pool parties, this dress boasts a flattering strapless neckline and bust cutout, a strappy back design, and a bodycon fit. Complete the look in sandals and sunnies!
Fit & Features
- Rib knit fabric, sewn-in knit lining, moderate stretch
- Strapless neckline
- Strappy back
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5767
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropical Blooms Floral Ruffle Chiffon Skater Dress
Let this tropical floral skater dress bloom into your summer lineup! With a sweetheart neckline featuring delicate ruffle trim, adjustable spaghetti straps and padded bra cups, this skater silhouette will flatter your figure. The mini-length hem adds a flirty touch to this tropical floral printed chiffon dress. Complete the look with a crossbody purse and sandals!
Fit & Features
- Tropical floral print
- Chiffon fabric with woven lining, no stretch
- Sweetheart ruffle trim neckline
- Padded bra cups
- Adjustable spaghetti straps
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3204
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sea You Later Chain Belt
Giving mermaid off-duty energy. This chain belt brings all the coastal cuteness with starfish and shell accents—wear it poolside, seaside, or whenever you’re channeling beach babe vibes.
Fit & Features
- Chain-link design
- Starfish and shell accents
- Adjustable fit with lobster clasp closure
Style Number/Barcode: 07301-000139
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Social Butterfly Charm Necklace
With an etched butterfly charm on a dainty chain, this necklace is a pretty piece for everyday wear. Complete the look with a stackable ring set.
Fit & Features
- Etched butterfly charm
- Dainty chain
- Lobster clasp closure
Style Number/Barcode: 07002-1865
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Cutie Strappy Faux Leather Sandals
Give off cutie vibes in these floral strappy faux leather sandals! They feature a round toe, an asymmetric strappy design with adorable flower accents with faux pearl center detailing, an adjustable ankle strap and heel strap, and a flat sole for comfortable wear. Style with a flowy summer dress for a perf summer look.
Fit & Features
- Faux leather upper
- Round toe
- Asymmetric strappy design
- Flower design with faux pearl center details
- Adjustable ankle strap, heel strap
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1213
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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She’s The Moment Tie-Front Halter Top
Serving main character energy with every knot—this top is that girl. The halter V-neck and flirty tie-fronts give it an effortlessly hot vibe that’s perf for your next weekend adventure.
Fit & Features
- Twill woven fabric
- Sleeveless halter V-neckline
- Multi-tie-front design
- Partially open back
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06003-000069
Category Name: Vacation Looks
Price: $36.90
Availability: Out of Stock
Product Badge:- Ships Free