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.
HomeVacation Looks

Vacation Looks
Product Recommendations
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.
-
Trendy Topic Strapless Denim Midi Dress
You'll be the topic of conversation in this denim midi dress for the trendiest look at casual hangs or brunch! This stunning denim dress features a strapless neckline and a form-hugging silhouette that will accentuate your curves. The belt loop accents and four-pocket styling add cute functional details, while the front center slit and midi-length hem provide a modern touch. Complete the look in sleek hoop earrings and pumps!
Fit & Features
- Denim fabric with minimal stretch
- Belt loops, four-pocket styling
- Front center slit
- Side zipper closure
- Form-hugging silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5455
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Simply Sleek Square-Shaped Sunglasses
Simply sleek and chic, these square-shaped sunglasses will level up your looks. They feature a small square-shaped design with tinted lenses, a thin metal frame with thin arms, a thin nose bridge, and rubber nose pads for support. Style with small hoop earrings for that trendy girl vibe!
Fit & Features
- Small square-shaped design
- Tinted lenses
- Thin metal frame and arms
- Thin nose bridge
- Rubber nose pads
Style Number/Barcode: 07008-1047
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Loved In Lace V-Neck Long Sleeve Short Dress
A divine lace short dress for modern brides, birthday babes, or any dressy occasion! The mini dress features sheer lace long sleeves with flared cuffs, a V-neckline, a bodycon silhouette that hugs your curves and is composed of a lace knit fabric with stretchy knit lining. Complete the look with fringe earrings and heels.
Fit & Features
- Sheer long sleeves, flared cuffs
- V-neckline
- Bodycon silhouette
- Short-length hem
- Lace knit fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-3171
Category Name: Vacation Looks
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
-
Chic Staple Square-Frame Sunglasses
These sleek and chic square-frame sunglasses will be a staple for the season! A trendy take on a classic design, these shades feature a square shape with a subtle angle, tinted lenses, a plastic frame, and mini-studded accents on each side. Style with hoop earrings.
Fit & Features
- Square-shaped design
- Tinted lenses
- Plastic frame and arms
- Studded accents
- Built-in nose pads
Style Number/Barcode: 07008-1049
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Brighten My Day Floral Mesh Duster
Brighten up your day by layering on this floral mesh duster over a cute swimsuit or sundress! It features fitted long sleeves, an open front, and a flowy longline hem on sheer airy mesh fabric with a blooming floral print. Complete the look with heeled sandals for the perfect vacation or weekend style!
Fit & Features
- Fitted long sleeves
- Open front design
- Flowy longline hem
- Blooming floral print
- Airy sheer mesh fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06202-0438
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Dreamy Destination Cutout Tropical Print Maxi Dress
Get ready to jet set to your dreamy destination with this sexy tropical maxi dress! The lightweight woven fabric showcases an abstract tropical print to bring that bold allure to your next getaway. The maxi-length dress features a sleeveless halter neckline with tie-back straps that can be styled as a criss-cross high neck or a sultry plunging design according to your fashion mood! The long dress has a chic center O-ring accent and eye-catching waist cutouts with thin straps that lead to an open back with a tie-back design. The flowy A-line fit will bring those breezy vibes, while the dual thigh-high side slits add a sexy silhouette. Complete your look with heeled sandals!
Fit & Features
- Tropical printed woven fabric
- Sleeveless halter neckline, tie-back straps
- Waist cutouts, O-ring accent
- Open back, lower tie-back straps
- Dual high-cut side slits
- Flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5356
Category Name: Vacation Looks
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Feelin' Trendy Cutout Woven Corset Top
You'll be feelin' trendy in this adorable corset top for your next night out! Made with a lined woven fabric, this crop top features a sleeveless square neckline and adjustable spaghetti straps for a customized fit. The flexible boning inserts add structure, while the back zipper offers effortless styling. The cropped fitted hem features side cutouts for a flirty touch. Style this corset top with faux leather pants and heels.
Fit & Features
- Woven fabric with sheer nylon-blend lining, minimal stretch
- Sleeveless square neckline
- Adjustable spaghetti straps
- Flexible boning
- Back zipper, hook and eye closure
- Cropped fitted hem with side cutouts
- Runs true to size
Style Number/Barcode: 06003-2395
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Stroll The Garden Mesh Floral Maxi Skirt
Stroll the garden in this mesh floral maxi skirt for an ethereal allure this season! It features a flattering high-rise waist, a form-hugging silhouette, and a center back slit for movement along the maxi-length hem. Complete the look with the matching bustier for a day date or party!
Shop Matching Top: Stroll The Garden Mesh Floral Bustier
Fit & Features
- High-rise waist
- Form-hugging silhouette
- Center back slit
- Maxi-length hem
- Floral garden print, mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 06501-0953
Category Name: Vacation Looks
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Stroll The Garden Mesh Floral Bustier
Stroll the garden in this mesh floral bustier for an ethereal allure this season! It features a strapless neckline, a bustier-style bodice with flexible boning inserts to provide structure, and a fitted mid-length hem. Complete the look with the matching maxi skirt for a day date or party!
Shop Matching Bottoms: Stroll The Garden Mesh Floral Maxi Skirt
Fit & Features
- Strapless neckline
- Bustier-style bodice
- Flexible boning, back zipper, hook and eye closure
- Fitted mid-length hem
- Floral garden print, lined mesh fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-5063
Category Name: Vacation Looks
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Strapless neckline
-
Stunning Vision Abstract Mesh Midi Dress
You'll be a stunning vision in this mesh midi dress out for a day date or brunch! It features a sleeveless square neckline, adjustable spaghetti straps, side ruching that accentuates your natural curves, and a flattering bodycon silhouette. The dress is designed with an artsy abstract print on mesh fabric and has a sewn-in knit lining. Complete the look with a trendy denim crop jacket.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Side ruching, bodycon silhouette
- Midi-length hem
- Abstract print, mesh fabric, sewn-in knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5496
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Lace To Remember Sleeveless Crop Corset Top
Transform any outfit into one to remember with this sleeveless woven corset top to bring a romantic allure on casual dates! The sleeveless design boasts a square neckline with delicate lace ribbon trim, adjustable spaghetti straps for a perfect fit, and flexible boning that flatters your figure. Style with denim jeans for an effortlessly cute look.
Fit & Features
- Woven fabric with knit lining
- Adjustable spaghetti straps
- Flexible boning
- Back zipper and hook-eye closure
- Lace ribbon trim
- Runs true to size
Style Number/Barcode: 06003-2396
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Day To Day Off-The-Shoulder Crop Top
Day to day, this off-the-shoulder crop top just gets cuter! It features fitted long sleeves with lettuce trim, a front adjustable drawstring lets you customize the style, and a slit accent along the lettuce trim hem on stretchy rib knit fabric. Complete the look with high-rise jeans for casual weekend plans!
Fit & Features
- Fitted long sleeves, lettuce trim
- Off-the-shoulder neckline
- Front adjustable drawstring, slit accent
- Cropped hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 06002-1718
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Pretty Babe Floral Off-The-Shoulder Corset Top
Effortlessly pretty will be your vibe in this floral corset top! Designed with an all-over blooming floral print pattern, the crop top features an off-the-shoulder neckline with the cutest ruffled trim, short fitted sleeves with tie strap accents, a built-in padded bust, complete hook and eye front closures, all-over ruching, and a form-hugging fit. The airy sheer mesh fabric includes a knit lining. Style with light-wash jeans and clear-heeled mules.
Fit & Features
- Off-the-shoulder sweetheart neckline, ruffled trim
- Short fitted sleeves, tie strap accents
- Padded bust, hook and eye front closures
- All-over ruching, fitted cropped hem
- Floral print
- Sheer mesh fabric, sewn-in knit lining, plenty of stretch
- Style runs small
Style Number/Barcode: 06001-4882
Category Name: Vacation Looks
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Chic Status Ruffled And Ruched Mini Dress
Achieve chic status serving looks in this on-trend ruffled and ruched mini dress! It features a sleeveless high boat neckline, an alluring open back with a V-cut design, ruffled accents at the shoulder and hem, ruching down the back and side seams to accentuate your curves, a mini-length hem with a ruffled trim, and a bodycon silhouette. The double-lined smooth knit fabric offers plenty of stretch. Style this short dress with lace-up stiletto heels for a party.
Fit & Features
- Sleeveless high boat neckline
- Open V-cut back design
- Ruffled accents at the shoulder and hem
- Ruched detailing down the back and side seams
- Mini-length hem, ruffled trim, bodycon fit
- Double-lined smooth knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05101-2896
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Irresistible Blooms Floral Strapless Maxi Dress
Steal all the stares in this floral mesh maxi dress for an irresistible look! This dreamy maxi-length dress features a sleek strapless neckline with non-slip grip lining, flexible boning inserts, side ruched seams that accentuate your curves, and a flattering bodycon silhouette. Complete the look with earrings and stiletto heels for a birthday or date night!
Fit & Features
- Strapless neckline, non-slip grip lining
- Side zipper and hook-eye closure
- Flexible boning inserts
- Side ruched seams, bodycon silhouette, maxi-length hem
- Floral garden print, mesh fabric, sewn-in knit lining
- Minimal stretch
- Runs true to size
Style Number/Barcode: 05101-3024
Category Name: Vacation Looks
Price: $6.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Jet Set For Sun Strapless Tropical Midi Dress
Jet set for fun under the sun in this tropical midi dress for endless compliments while on vacation! The midi-length dress features a strapless neckline, a form-hugging silhouette, a flirty side slit and asymmetrical hem, and an adjustable side drawstring so you customize the style. Complete the look in sandals for a sunset dinner!
Fit & Features
- Strapless neckline
- Form-hugging silhouette
- Adjustable side drawstring, side slit
- Asymmetrical midi-length hem
- Tropical print, mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5486
Category Name: Vacation Looks
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Artsy Vibes Abstract Print Mesh Bodysuit
Give off those cool artsy vibes in this abstract mesh bodysuit! Designed with a trendy abstract print on the sheer mesh fabric, the bodysuit features a crew neckline, long fitted sleeves, a thong-cut bottom with snap button closures, and a form-hugging fit. Style with a mini skirt and clear heels for a fab party 'fit.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Thong-cut bottom, dual snap button closures
- Form-hugging fit
- Abstract print
- Sheer mesh fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-5022
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Bold Babe Status Chain Print Chiffon Duster
Show off your bold babe status with this eye-catching and chic chiffon duster. It features a V-neckline, a smocked high waist with a partial button-down front, long sleeves with cinched smocked hems, and a flowy high-low silhouette with a ruffled front design. The airy chiffon fabric features a chain-link and scroll multi-print pattern. Layer over a bodysuit with faux leather pants and heels.
Fit & Features
- V-neckline
- Smocked high waist, button-down front
- Long sleeves, smocked hems
- Flowy high-low silhouette, ruffled front design
- Chain-link and scroll multi-print pattern
- Sheer chiffon fabric
- Runs true to size
Style Number/Barcode: 06204-1072
Category Name: Vacation Looks
Price: $14.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Table For Two Floral Lace-Up Corset Top
Serve the main entree look in this floral jacquard corset top! Boasting a strapless angled neckline, this corset features a stunning satin lace-up back for a snatched look and a fitted curved crop hem perfect for flaunting your figure. The flexible boning inserts add structure to the bodice. Complete the look in high-rise denim jeans for a chic style!
Fit & Features
- Strapless angled neckline
- Satin lace-up back, tie closure
- Flexible boning inserts
- Fitted curved hem
- Floral jacquard pattern
- Woven fabric, knit lining, no stretch
- Runs true to size
Style Number/Barcode: 06003-2386
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Carolina Formal Fringe High Neck Maxi Dress
Special Occasion
Old Hollywood with flapper flair, the Carolina formal fringe maxi dress sways with every move you make! She brings modern glamour with her sleeveless high neckline, spaghetti halter straps, a form-hugging silhouette, and a curved long-length hem. The formal maxi dress is designed with fringe detailing throughout a smooth knit fabric that enhances your curves and adds some drama to the night. Complete the look with rhinestone PVC pumps for a cocktail party or banquet!
Fit & Features
- Sleeveless high neckline, spaghetti halter straps
- Back zipper and hook-eye closure
- Form-hugging silhouette
- Curved maxi-length hem
- Fringe detailing, smooth knit fabric, slight stretch
- Pasties recommended
- Runs true to size
Style Number/Barcode: 05001-2126
Category Name: Vacation Looks
Price: $59.97 $119.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Chilly Season Faux Fur Bucket Hat
This adorable faux fur bucket hat is the perf accessory for the chilly season! It features a classic bucket hat design with a short brim and is composed of an ultra-plush faux fur material with a woven lining. Style with a cable knit sweater for the cold winter months!
Fit & Features
- Classic bucket hat design
- Short brim
- Soft faux fur exterior
- Woven lining
Style Number/Barcode: 07302-1542
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Feeling Bliss Rib Knit Pajama Tank Top
Experience comfort and bliss in this soft pajama crop top! Its round neckline, racerback design, fitted elasticized crop hem, and soft rib knit fabric ensure a cute and cozy lounge. Complete the look with the matching pajama bottoms.
Shop Matching Bottoms: Feeling Bliss Rib Knit Pajama Pants
Fit & Features
- Sleeveless round neckline
- Racerback design
- Fitted elasticized crop hem
- Soft rib knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07103-0954
Category Name: Vacation Looks
Price: $9.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Total Trendsetter O-Ring Chain Belt
This sleek O-ring chain belt was made to complete your trendy 'fits! It features an all-around linked O-ring design and includes an adjustable fit with a lobster clasp closure. Style over a bodycon dress with strappy stilettos for a fab going-out look.
Fit & Features
- Linked O-ring design
- Adjustable fit
- Lobster clasp closure
Style Number/Barcode: 07301-0702
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Linked O-ring design
-
Stunning Destination Tropical Ruffle Maxi Dress
Arrive at your destination in this tropical maxi dress looking stunning and ready for fun! The maxi dress features a strapless neckline, non-slip grip lining, flexible boning, a form-hugging fit, and an effortless high front slit and ruffled flowy hem. Complete your vacation look with a handbag and sandals!
Fit & Features
- Strapless neckline, non-slip grip lining
- Back zipper and hook-eye closure
- Flexible boning
- Form-hugging fit
- High front slit, ruffled flowy maxi hem
- Tropical print, airy mesh fabric, partial knit lining
- Runs true to size
Style Number/Barcode: 05102-5383
Category Name: Vacation Looks
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale