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.
-
A Dressy Affair Straw Platform Heels
Dress up your casual outfits with platform heels that wow! The heels feature an adjustable ankle strap, an open almond toe with a strap over the toe, a straw platform, and a straw block heel. Complete look with a romper and door knocker earrings.
Fit & Features
- Adjustable ankle strap
- Open almond toe with strap over the toe
- Platform
- Straw platform and block block
- Faux leather material
Style Number/Barcode: 07401-2916
Category Name: Vacation Looks
Price: $12.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
A Little Bit Of Everything Hoops Multipack
Rock a pair of hoops for your glam and basic moods! This multipack features three pairs of hoops that feature a filigree design, a basic flat metal, and a glitter embellished design. Complete look with a romper and hoops for a brunch-ready look!
Fit & Features
- Pack includes three pairs of hoops
- Filigree
- Basic
- Glitter
- Omega back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0715
Category Name: Vacation Looks
Price: $6.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Make Hearts Flutter Tie Front Top
Make hearts flutter with a cute crop top that brings chic details! The top features a plunging V-neckline with a tie front accent, short flutter sleeves, and a cropped hem. Complete look with high-rise pants and platform heels.
Fit & Features
- V-neckline
- Tie-front accent
- Short flutter sleeves
- Cropped hem
- Gauze knit fabric
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-0949
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Level Up Cutout Knit Jumpsuit
Level up your style with a jumpsuit that brings sexy details that keep you on-trend! The jumpsuit features a plunging V-neckline with halter neck ties, dual waist cutouts, a lower back keyhole, and a straight leg. The jumpsuit is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Halter neck ties
- Lower back keyhole
- Dual waist cutouts
- Straight leg
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0549
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Two Band Rhinestone Jelly Slides
Buckle up in these glam sandals that feature an open almond toe, a double-band buckle design, rhinestone embellishments, and a jelly body. Complete look with a bustier and mini skirt.
Fit & Features
- Open almond toe
- Double-band buckle design
- Rhinestone embellishments
- Jelly body
Style Number/Barcode: 07404-0849
Category Name: Vacation Looks
Price: $7.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Summer Vibes Strappy Sandals
Bring on those summer vibes with these casual-chic sandals! They feature an open round toe, a woven straw toe strap and adjustable ankle strap, a faux leather heel strap, and a flat sole. Style these sandals with a crop top and denim shorts.
Fit & Features
- Open round toe
- Woven straw toe strap
- Woven straw ankle strap, adjustable fit
- Faux leather heel strap
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-0822
Category Name: Vacation Looks
Price: $12.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Glitz And Glam Glitter Straw Floppy Hat
Channel a glam look with a floppy hat that dazzles up your vacation outfits! The hat features a fitted brim, a double-row glitter trim, and a floppy design. Complete look with a smocked dress and wedges.
Fit & Features
- Fitted brim
- Double-row glitter trim
- Floppy design
- Straw material
Style Number/Barcode: 07302-0312
Category Name: Vacation Looks
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Romantic Beauty Mini Dress
Bring the romantic vibes to date night with this beautiful mini dress. It features a sleeveless square neckline, adjustable spaghetti straps, ruched detailing, and a mini-length, curve-hugging silhouette. The mesh fabric has an all-over blooming floral print, making the dress a perf option for summer. Complete the look with dainty earrings and new heels.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Back zipper closure
- Ruched detailing
- Short, form-hugging fit
- Floral printed mesh fabric
- Runs true to size
Style Number/Barcode: 05101-0967
Category Name: Vacation Looks
Price: $14.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Fab Florals Crochet Waist Maxi Dress
Impress with florals in a maxi dress that takes you to paradise! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a crochet waist, a floral print, a high side slit, and a maxi length silhouette. The dress is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Crochet waist
- Floral print
- High side slit
- Maxi length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-0196
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Tropical Dream Sleeveless Mini Dress
Dream up the perfect vacation look with a mini dress that channels those vibes! The dress features a sleeveless scoop neckline, adjustable spaghetti straps, lace-up back, a tropical print, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps
- Lace-up back
- Tropical print
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-0665
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Look At Her Lucite Wedges
Make them take notice with these stunning wedges. The wedges feature an open back, an almond toe with a thong strap, and a lucite wedge heel. Complete look with a crop top and mini skirt.
Fit & Features
- Open back
- Almond toe
- Thong strap
- Lucite wedge heel
Style Number/Barcode: 07406-0261
Category Name: Vacation Looks
Price: $7.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Ruffle Me Up Crop Top
Flirty, flowy, and made for vacay vibes! This ruffle-trim crop top brings soft drama with a sleek fit and tie-front design that shows just enough—pair it with the matching skirt to complete the look.
Shop The Matching Skirt: Ruffle Me Up Midi Skirt
Fit & Features
- Smooth double-lined stretchy knit fabric
- Ruffled trim front
- Tie front closure
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06202-000040
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Reign In Glam Rhinestone Slides
Reign the day with glam flat slides that take your casual outfits to the next level! The slides feature an easy slip-on design, an open almond toe, and a wide rhinestone embellished strap. Complete the look with a glitzy crossbody bag.
Fit & Features
- Slip-on design
- Open almond to
- Wide rhinestone toe strap
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-0695
Category Name: Vacation Looks
Price: $12.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Strappy And Stylish Lace-Up Sandals
These strappy lace-up sandals will give your summer look a stylish vibe! They feature an open round toe, a thin strappy lace-up design with a tie-back detail, and a flat sole. Pair these sandals with a casual dress and a cute boater hat.
Fit & Features
- Open round toe
- Thin strappy lace-up design
- Tie-back detail
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-0805
Category Name: Vacation Looks
Price: $12.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
So Extra Lace Up Block Heels
You'll be looking so extra in these glam heels! The heels feature sleek lace-up straps, an open almond toe with a trendy thong strap, and a block heel. Complete look with a bodycon and clutch.
Fit & Features
- Lace-up straps
- Open almond toe
- Thong strap
- Block heel
- Faux suede material
Style Number/Barcode: 07401-2682
Category Name: Vacation Looks
Price: $12.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Bohemian Chic Straw Block Heels
Channel those boho vibes with heels that bring those earthy vibes. The heels feature an adjustable asymmetrical ankle strap with a wide metal buckle, an open almond toe with straw material, and a low block heel. Complete look with a ditsy floral dress and a straw tote.
Fit & Features
- Adjustable asymmetrical ankle strap
- Open almond toe
- Straw material
- Low block heel
Style Number/Barcode: 07401-2805
Category Name: Vacation Looks
Price: $7.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Basic Snake Print Thong Sandals
Slip on these sandals to keep your look on point! The sandals feature an open almond toe, snake print thong strap, and a faux leather footbed. Complete the look with a basic tee and shorts for a laid-back look.
Fit & Features
- Open almond toe
- Snake print thong strap
- Faux leather footbed
Style Number/Barcode: 07404-0815
Category Name: Vacation Looks
Price: $9.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Go With The Flow Maxi Dress
Go with the flow of this gorgeous maxi dress! It features a sleeveless deep V-neckline with a lined crochet lace top, adjustable spaghetti straps, a tie-back detail with a lower back cutout, and a flowy, floor-length skirt with pleated detailing and a relaxed fit. Style this dress with new earrings and strappy sandals for your summer vacay.
Fit & Features
- Sleeveless deep V-neckline
- Lined crochet lace top
- Adjustable spaghetti straps
- Tie-back detail, lower back cutout
- Floor-length skirt, pleated detailing
- Relaxed fit
- Gauze fabric
- Runs true to size
Style Number/Barcode: 05102-0295
Category Name: Vacation Looks
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Wide Fit Double Band Croc-Embossed Sandals
Slip on these sandals to make a stylish statement this season! The sandals feature an easy slip-on design, a double-row strap design with faux croc-embossing, and a wide-fit footbed for added comfort.
Fit & Features
- Slip-on design
- Open almond toe
- Double-row strap design
- Faux croc embossing
- Wide-fit footbed
- Faux leather
Style Number/Barcode: 07404-0778
Category Name: Vacation Looks
Price: $12.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Hit The Tropics Double Strap Bow Sandals
These sandals will have you ready to hit the tropics! The sandals feature a slip-on design, an open almond toe, a double row of straps accented with bows, a tropical palm leaf print, and a faux suede insole. Complete look with cutoff shorts and a crop top.
Fit & Features
- Slip-on design
- Double row of straps with bows
- Tropical palm leaf print
- Faux suede insole
- Straps composed of faux leather with a woven canvas exterior
Style Number/Barcode: 07404-0814
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Gorgeous Getaway Maxi Dress
This stunning printed maxi dress will have you looking absolutely gorgeous for your next weekend getaway! It features a sleeveless square neckline, spaghetti straps, a flowy, floor-length silhouette, and a sultry thigh-high side slit. The knit fabric has an all-over tropical palm leaf print, making the dress a perf option for a summer vacay. Style it with wedges and a chic pair of sunglasses.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Floor-length silhouette, high side slit
- Relaxed fit
- Knit fabric, palm leaf print
- Runs true to size
Style Number/Barcode: 05102-0654
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Places To Be Square Faux Nubuck Wedges
Places to be, people to see! Change out your old wedges for something a little different! The wedges feature a slip-on design, a wide strap over the toe, and a square toe. Complete the look with a denim jumpsuit and hoops.
Fit & Features
- Slip-on design
- Wide strap over the toe
- Wide strap over the toe
- Square toe
- Faux nubuck material
Style Number/Barcode: 07406-0251
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Stylish Stunner Double Strap Bow Sandals
These sandals will have you ready to make a stylish impression! The sandals feature a slip-on design, an open almond toe, a double row of straps accented with bows, and a faux suede insole. Complete look with cutoff shorts and a crop top.
Fit & Features
- Slip-on design
- Double row of straps with bows
- Faux suede insole
- Straps composed of woven canvas material
Style Number/Barcode: 07404-0813
Category Name: Vacation Looks
Price: $11.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Stylish Straps Faux Leather Sandals
Keep it stylish with sandals that keep your look on point! The sandals feature an adjustable cross-strap at the ankle, an open square toe with a double row of straps, and a low block heel. Complete the look with a floral mini dress and clutch.
Fit & Features
- Open back
- Adjustable cross-strap at the ankle
- Open square toe
- Double row of straps over the toe
- Low block heel
- Faux leather material
Style Number/Barcode: 07404-0807
Category Name: Vacation Looks
Price: $12.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free