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.
HomeVacation Looks
Vacation Looks
Now Trending
STYLE SPOTLIGHT
Get Eye-Catching Sandals For Women
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.
-
Casual Staple Wrap-Front Mini Dress
Update your wardrobe with this cute and casual mini dress that is a stylish staple! It features a crew neckline, short sleeves, a trendy wrap-front design at the waist with a tie closure, a form-hugging fit, and a mini-length hem. The soft brushed knit fabric offers plenty of stretch for comfort. Complete the look with ankle booties.
Fit & Features
- Crew neckline
- Short sleeves
- Wrap-front design at the waist, tie closure
- Form-fitting silhouette
- Mini-length hem
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5007
Category Name: Vacation Looks
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Feline Fierce High-Slit Midi Skirt
You'll be feelin' fab and fierce in this adorable leopard printed midi skirt. It features a high-rise waist, a chic high front slit, and a mid-length, relaxed silhouette. Style this skirt with a basic bodysuit and cute mules.
Fit & Features
- High-rise waist, elastic-band
- High front slit
- Mid-length, relaxed silhouette
- Lightweight knit fabric, moderate stretch
- Leopard print
- Runs true to size
Style Number/Barcode: 06501-0513
Category Name: Vacation Looks
Price: $6.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Fruity Delight Three-Pack Earrings Set
Freshen up your accessories with this three-pack earrings set for a delicious spring season! the set features one pair of rhinestone cherries, one pair of strawberries, and one sleek ball studs. Pair with a shoulder bag.
Fit & Features
- Three-pack set
- One rhinestone cherry pair, post-back closure
- One strawberry pair, clasp closure
- One ball stud pair, post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2300
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Adorable Factor Chiffon Sweetheart Midi Dress
Raise the bar looking adorable in this chiffon midi dress perfect for upcoming dressy occasions! The midi-length dress features short puff sleeves, a sweetheart neckline, a ruched bust, and a flirty cutout waist to show some skin. The flattering A-line silhouette boasts a playful front slit and a flowy midi hem. Complete the look with cute sandals and jewelry!
Fit & Features
- Short puff sleeves
- Sweetheart neckline, stretchy smocked back
- Ruched bust, cutout waist
- A-line silhouette, front slit
- Midi-length hem
- Chiffon woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 05101-3189
Category Name: Vacation Looks
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Truly Charming Sleeveless A-Line Mini Dress
Unlock a truly charming style in this sleeveless mini dress at BBQs to summer picnics! Features a square neckline and adjustable spaghetti straps for the perfect fit. Its A-line silhouette flatters every figure, and the mini-length hem adds flirtatiousness. Complete the look with sunglasses and wedges.
Fit & Features
- Woven fabric, minimal stretch
- Square neckline
- Adjustable spaghetti straps
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5704
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Tropical Vacay Spaghetti Strap Tie-Back Crop Top
The perfect tropical floral crop top to look stylish on your vacay! With its sleeveless V-cut neckline with ruching at the bust, spaghetti straps, and a tie-back design, this top offers a trendy silhouette. The fitted ultra-cropped hem and eye-catching tropical floral print add a touch of boldness to your look. Pair with the matching midi skirt and espadrille wedges!
Shop Matching Bottoms: Tropical Vacay High-Rise Slit Midi Skirt
Fit & Features
- Tropical floral print
- Stretchy knit fabric
- V-wired neckline, ruched bust
- Spaghetti straps
- Tie-back design
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06001-5221
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Places To Be Off-The-Shoulder Top
You've got places to be so don't compromise your style! This off-the-shoulder top creates an effortlessly cute look with your favorite bottoms. It features dolman long sleeves with fitted cuffs, a slouchy bodice, and a fitted hem on stretchy textured knit fabric. Complete the look in best-selling jeans.
Fit & Features
- Off-the-shoulder
- Dolman long sleeves, fitted cuffs
- Slouchy bodice
- Fitted hem
- Textured knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4638
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Pretty Pleats High-Rise Chiffon Palazzo Pants
Pretty pleats make these high-rise palazzo pants a chic find! Style with a crop top and heels for dinner and drinks.
Fit & Features
- Chiffon woven fabric, knit lining
- High-rise waist
- Wide-leg pleated silhouette
- Runs true to size
Style Number/Barcode: 06402-1465
Category Name: Vacation Looks
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Girly Fave Ruffled Eyelet Knit Romper
This eyelet knit romper will be your new girly fave for the summer months! Designed with a strapless neckline, drop waist, and tiered ruffled overlay, style with sneakers.
Fit & Features
- Eyelet knit fabric
- Strapless straight neckline
- Drop waist design
- Tiered ruffled mini-length overlay
- Hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06503-000022
Category Name: Vacation Looks
Price: $15.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Snap To It Tweed Tank Mini Dress
Snap into this nineties-inspired tweed mini dress to have your major fashion moment! It features a sleeveless square neck, wide shoulder straps, and a bodycon fit. The dress is composed of a multi-colored stitch tweed woven fabric with a smooth satin lining with no stretch. Style with a cropped blazer to complete the look!
Fit & Features
- Sleeveless square neck
- Wide shoulder straps
- Back zipper and hook-eye closure
- Bodycon fit, mini-length hem
- Multi-colored stitch tweed fabric
- Smooth satin lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-2245
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Darling Flirtation Tie Strap V-Neck Floral Mini Dress
Imagine how darling and flirty you'll be in this floral mini dress at brunch and parties! The delicate floral print on brushed knit soft fabric adds a playful and romantic touch, perfect for any occasion. Features a plunging neckline and charming tie straps to accentuate your curves while the bodycon fit and mini-length hem add a touch of allure. Complete the look in cute sandals.
Fit & Features
- Floral print, brushed knit fabric lined with stretchy knit
- Tie straps, V-neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5589
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Spine Chilling Eyelash Knit Sweater
This eyelash knit sweater may give you chills at how cute it is! The sweater features long sleeves with cuffs, a mock neckline, cropped hem, and a partial open-back design with tie closure. Complete the look in a mini skirt and boots.
Fit & Features
- Long sleeves with cuffs
- Mock neckline
- Cropped hem
- Partial open-back design tie closure
- Fuzzy eyelash knit
- Fits true to size
Style Number/Barcode: 06005-1480
Category Name: Vacation Looks
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Sweeten Up Strappy Back Floral Chiffon Skater Dress
Sweeten up any moment in this floral chiffon skater dress perfect for celebrations and showers! With a square neckline, spaghetti straps, and a playful strappy back design, this dress is perfect for any occasion. The skater silhouette and ruffled short-length hem add a flirty touch, while the ditsy floral print and chiffon fabric keep it light and whimsical. Complete the look in wedges.
Fit & Features
- Ditsy floral print, chiffon fabric lined with stretchy knit
- Spagehtti straps, square neckline
- Strappy back design
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5450
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
There She Goes High-Rise Slit Boyfriend Jeans
These denim boyfriend jeans were made to be seen on you! They feature a flattering high-rise waist, trendy relaxed boyfriend style leg with knee slit accents on premium denim fabric. Style with a chic corset top for dinner and drinks with your honey!
Fit & Features
- High-rise waist
- Relaxed boyfriend-style leg
- Knee slit accents
- Front five-button closure
- Five-pocket styling, belt loop accents
- Premium denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06602-0428
Category Name: Vacation Looks
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Simple Glam Moment Bodysuit
Showcase simple glam vibes in this glitter knit bodysuit that was made for a night out. It features a wrap-front design with a V-neckline, long fitted sleeves, a high waist seam, and a knit bottom. Style this shimmery bodysuit with faux leather pants and strappy heels.
Fit & Features
- Wrap-front design, V-neckline
- Long fitted sleeves
- High waist seam
- Knit bottom
- Glitter knit fabric
- Runs true to size
Style Number/Barcode: 06001-4482
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Elevated Sleek Faux Leather Blazer
Layer on this elevated sleek faux leather blazer for a city-chic vibe. It features a lapel collar, long cuffed sleeves, front pockets, and a relaxed silhouette. The patent faux leather fabric offers a moderate stretch. Style with hoop earrings and a chain necklace.
Fit & Features
- Lapel collar
- Long sleeves, cuffed hems
- Front pockets
- Long-length hem
- Relaxed fit
- Patent faux leather fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06204-1485
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Cute Adventures Halter Tie Front Crop Top
A halter crop top for all of your cute adventures this season! This top is designed with a flirty dual tie-front design and a bold center split and delicate sheer crop hem create the perfect balance of daring and feminine charm.
Fit & Features
- Crinkle texture sheer woven fabric, bust lining
- Plunge halter neckline with tie closure
- Dual tie front
- Center split, sheer crop hem
- Runs true to size
Style Number/Barcode: 06003-000039
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Too Cute To Catch Belted Ruffle Skort
Catch her if you can—she’s booked, busy, and best dressed. This ruffled mini skort brings all the bounce for brunch, day parties, and spontaneous Insta moments.
Fit & Features
- Woven fabric
- High-rise belted waist, belt loop accents
- Hidden side zipper and hook-eye closure
- Ruffled skirt overlay, shorts lining
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06403-000025
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Country Vibes Cowboy Boot Bag
Show off those trendy country vibes with this adorable cowboy boot bag! Featuring a cowboy boot shape with a center star accent, a cow print pattern, and an included chain-link shoulder strap, this bag is perfect for music festivals to keep all of your essentials on hand. Style with a rhinestone fringe denim jacket and boots!
Fit & Features
- Cowboy boot shape
- Center star accent
- Cow print pattern
- Top zipper closure
- Included chain-link shoulder strap
- Faux leather material, woven interior
Style Number/Barcode: 07203-1151
Category Name: Vacation Looks
Price: $19.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Wild Thing High Rise Zebra Print Skort
Get wild for this zebra print skort and flaunt your fierceness! Featuring a high-rise waist and form-hugging fit, a front skirt overlay adds a touch of flirty fun, while the short lining offers comfort and coverage. Complete the look with the matching top.
Shop Matching Top: Wild Thing Corset Zebra Print Top
Fit & Features
- Zebra print, woven fabric, no stretch
- High rise waist
- Back zipper and hook-eye closure
- Form-hugging fit
- Skirt overlay, shorts lining
- Runs true to size
Style Number/Barcode: 06303-0252
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Flirty Ditsy Floral Eyelet Strapless Mini Dress
Keep your summer date 'fits flirty and stylish with this floral eyelet strapless mini dress! The airy lightweight eyelet knit fabric is detailed with a sweet ditsy floral print and features a brushed knit lining for coverage. The mini-length dress is shaped with a strapless straight-across elasticized neckline for added stretch and a bodycon silhouette to highlight your curves. Pair with platform sandals and hoop earrings.
Fit & Features
- Ditsy floral print
- Stretchy eyelet knit fabric with knit lining
- Strapless straight neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5799
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sultry Classic Plunge V-Neck Top
Ultra flattering and essential, this plunge v-neck top features long bishop sleeves and a ruched bodice for a figure-hugging fit. Complete the look in high-rise jeans for a dinner party.
Fit & Features
- Long bishop sleeves
- Plunge v-neck
- Ruched bodice
- Figure-hugging fit
- Sleek knit fabric
- Fits true to size
Style Number/Barcode: 06001-4393
Category Name: Vacation Looks
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Trendsetting Vibes Faux Leather Shacket
Showcase chic trendsetting vibes when you layer on this sleek faux leather shacket. It features a collared neckline, long sleeves, a complete button-down front, buttoned chest pockets, and a relaxed fit. The smooth faux leather fabric offers a moderate stretch. Style over a basic bodysuit with your fave pair of denim.
Fit & Features
- Collared neckline
- Long sleeves, single button detail
- Button-down front
- Buttoned chest pockets, dual lined side pockets
- Relaxed fit
- Faux leather fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-1369
Category Name: Vacation Looks
Price: $21.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Pop Star Rhinestone High-Rise Denim Shorts
Put on a show arriving in these rhinestone denim shorts! They feature a flattering high-rise waist, and stunning rhinestone swag chains across the front for a touch of glamour. The distressed accents add a trendy edge, while the fitted hem ensures a perfect fit. Complete the look in a bodysuit and boots for a concert or music festival!
Fit & Features
- High-rise waist
- Rhinestone swag chains across the front
- Distressed accents, fitted hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Medium wash denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06603-0364
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free