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.
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.
-
Sunkissed Chic Cutout Crochet Maxi Dress
Resort plans just got a plot twist. This beaded crochet maxi dress serves sculpted curves with a sweetheart neckline, waist cutout, and chic bead details made for walking in and turning heads.
Fit & Features
- Crochet knit fabric with knit lining, moderate stretch
- Sleeveless sweetheart neckline, U-wired metal insert, beaded fringe design
- Padded bust, waist cutout
- Adjustable spaghetti straps
- Back zipper with hook-eye closure
- Maxi-length hem, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-001474
Category Name: Vacation Looks
Price: $59.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
-
Low Key Drama Open Back Plunge Dress
A dramatic neckline and an open back make this one an instant standout. This flowing dress pairs a plunging front with airy draped sleeves and a side-tie detail for an effortlessly elevated look with beautiful movement. Perfect for vacations, dinner dates, and special occasions where an unforgettable entrance is part of the plan.
Fit & Features
- Silky satin fabric, sewn-in woven lining
- Plunging V-neckline
- Open-back design, adjustable strap, lower zipper and hook-eye closure
- Draped long sleeves with side tie accents
- Curve-hugging mini-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001334
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: WINE
Available Size: XS, S, M, L
Product Badge:- New Arrival
-
Paradise In Floral Midi Dress
The RSVP practically sends itself. This tropical floral midi dress features a breezy asymmetric hem and flattering halter neckline that was made for destination weddings, dinners, and vacation photos.
Fit & Features
- Abstract floral print, mesh-lined fabric
- Halter V-neckline
- Spaghetti straps
- Ruffled trim
- Flowy midi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000813
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: PINK-2
Available Size: XS, S, M, L
Product Badge:- New Arrival
-
Amara Mesh Halter A-Line Formal Dress
Special Occasion
Easy, alluring, and made for warm-weather RSVPs, the Amara mesh A-line gown brings a breezy kind of drama to every step. A ruched halter bodice, front cutout, and double-slit skirt create movement that feels effortless, polished, and just a little unforgettable.
Fit & Features
- Mesh fabric, full coverage panty knit lining
- Halter neckline, tie straps, padded bra cups
- Open tie-back design
- Thigh-high front slit
- Flowy A-line floor-length silhouette
- Runs true to size
Where to Wear:
Destination weddings, beach weddings, honeymoons, vacations, resorts, birthday dinners, cocktail events, bachelorette weekends, sunset celebrations, yacht parties
Style Number/Barcode: 05002-001671
Category Name: Vacation Looks
Price: $69.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
-
Bead Side Halter Maxi Dress
Minimal effort, major impact. This textured knit maxi dress brings a halter neckline, curve-skimming fit, and side cutouts with bead accents for dinner plans, vacations, and every invite that calls for something sleek.
Fit & Features
- Texture knit fabric
- Halter neckline
- Side cutouts with beaded straps
- High center back slit
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-001472
Category Name: Vacation Looks
Price: $56.90
Availability: In Stock
Available Color: BROWN-2
Available Size: XS, S, M, L
Product Badge:- New Arrival
-
Flirt First Flutter Sleeve Crop Top
A little flounce, a lot of attitude. This flutter sleeve crop top brings the cinched tie-front detail and shoulder-baring fit your jeans have been waiting for.
Fit & Features
- Gauze woven fabric
- Sweetheart neckline
- Cinched tie-front design
- Short flutter sleeves, can be worn off-the-shoulder
- Smocked back
- Ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06003-000065
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: RED
Available Size: XS, S, M, L
Product Badge:- New Arrival
-
Shore Thing Statement Earrings
These iridescent shell drop earrings pair luminous shine with textured metal accents for a look that feels equal parts beach treasure and polished statement.
Fit & Features
- Textured accent
- Iridescent shell drop silhouette
- Post-back closure
Earrings are final sale and may not be returned or exchanged
Style Number/Barcode: 07001-000405
Category Name: Vacation Looks
Price: $10.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival
-
Bloom Snap Flower Hair Clips
Your quick hair fix just got way cuter. This two-pack flower hair clip set brings a glossy petal design with claw clip closures for easy updos and half-up styles.
Fit & Features
- Two-pack hair clip set
- Tropical flower designs
- Claw clip closure
Style Number/Barcode: 07006-000139
Category Name: Vacation Looks
Price: $10.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: NS
Product Badge:- New Arrival
-
Treasure Box Two-Piece Ring Set
Why choose one statement ring when you can have a whole lineup? These colored statement gemstone stretch rings feature bold square and oval stones that instantly add personality, polish, and a little extra fun to every outfit.
Fit & Features
- Two-pack ring set
- Statement designs
- Colored gemstone insets
- Stretch fit bands
Style Number/Barcode: 07004-000144
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
Product Badge:- New Arrival
-
Talia Chevron Cutout Mermaid Dress
Special Occasion
Made for golden hour plans and every sunshine moment, the Talia mermaid dress brings resort-minded allure with an effortlessly sculpted finish. Designed in chevron knit with a sleek floor-length silhouette, front and side cutouts, and beaded strap details, it is your answer to sunset dinners, rooftop parties, and summer nights that call for a little extra.
Fit & Features
- Sheer knit fabric with an abstract chevron pattern, full-length knit lining, moderate stretch
- Sleeveless plunging V-neckline, padded bust
- O-ring cutout, waist cutouts, beaded strap design
- Adjustable spaghetti straps
- Open back, back strap with metal bar closure
- Floor-length mermaid silhouette
- Runs true to size
Where to Wear:
Vacations, resorts, brunch with the girls, sunset dinners, rooftop parties, and summer nights out.
Style Number/Barcode: 05002-001724
Category Name: Vacation Looks
Price: $69.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
Product Badge:- New Arrival
- Sheer knit fabric with an abstract chevron pattern, full-length knit lining, moderate stretch
-
Jet Set Rhinestone Tropical Floral Tube Top
Your outfit just booked the trip. This rhinestone tropical floral tube top brings a bright statement print, strapless neckline, and curve-hugging fit made for rooftop plans, resort dinners, and every photo that makes the group chat pause.
Fit & Features
- Knit fabric, high stretch
- Large tropical floral print, rhinestone embellishments
- Strapless straight-across neckline
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000712
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
Product Badge:- New Arrival
-
Shade Check Cat Eye Sunglasses
Incognito, but make it intentional. These cat-eye sunglasses feature a sleek, angled frame that instantly sharpens errands, brunch looks, and coffee runs.
Fit & Features
- Plastic cat-eye sunglasses silhouette
- Tinted lenses
- Sleek angled frame
- 100% UV protection
Style Number/Barcode: 07008-000156
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
Product Badge:- New Arrival