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.
-
Sweet Spice Corset Lace-Up Floral Midi Dress
Sweet and spice combine on this floral midi dress designed with a stylish lace-up back, corset bodice, and a flirty front slit for movement. Complete the look with mules.
Fit & Features
- Ditsy floral print, smooth woven fabric, woven lining
- Sleeveless sweetheart neckline with tie
- Shoulder straps, side zipper and hook-eye closure
- Lace-up back design
- Underwire bust, corset bodice
- Front slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-3819
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Delicate Essence Puff Sleeve Corset Lace Mini Dress
The delicate essence of this lace mini dress will have you looking so cute at a bridal shower, as the birthday girl or graduate! Featuring sheer puff sleeves, an underwire bust for support, and flexible boning for a flattering bodycon fit. The front ruched seam adds a touch of sophistication to this playful mini-length dress. Complete the look in cute sandals and a purse!
Fit & Features
- Lace fabric lined with stretchy knit
- Back zipper and hook-eye closure
- Sweetheart neckline, underwire bust
- Flexible boning
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3226
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Flirt And Twirl Puff Sleeve Tie-Back Skater Dress
Flirt and twirl in this cute skater dress at parties and day dates! The puff short sleeves and square neckline add a touch of charm, while the tie-back design and skater silhouette create a flattering fit. Complete the look with hoop earrings.
Fit & Features
- Crepe woven fabric, stretchy knit lining
- Square neckline
- Tie-back detail
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3243
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Love's In The Air Floral Chiffon A-Line Dress
Slip into romance! This dainty floral chiffon short dress features a sweetheart neckline and bust tie to accentuate your figure while the wide shoulder straps and underwire bust provide support. The corset-trim bodice and back lace-up design add a touch of romance along the flattering A-line silhouette and short-length hem. Complete the look with a ring set and sandals for a date or brunch!
Fit & Features
- Sleeveless sweetheart neckline
- Wide shoulder straps
- Underwire bust, tie front, side zipper and hook-eye closure
- Corset-trim bodice, lace-up back design
- A-line silhouette, short-length hem
- Dainty floral print, chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-3007
Category Name: Vacation Looks
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Fresh Vibe High-Rise Destructed Straight-Leg Jeans by Windsor Denim
These trendy destructed straight-leg jeans by Windsor Denim will give you that fresh vibe you crave for the summer season. Made with a stretchy cotton-blend denim fabric, they feature a high-rise waist and a straight-leg fit with destructed detailing for an effortlessly cool look. Include a five-pocket and belt loop design with a front button and hidden zipper closure. Style these jeans with a graphic tee and ankle booties.
Fit & Features
- Cotton-blend denim fabric with moderate stretch
- High-rise waist
- Straight-leg fit
- Destructed detailing
- Five-pocket and belt loop design
- Front button, zipper closure
- Runs true to size
Style Number/Barcode: 06602-0492
Category Name: Vacation Looks
Price: $6.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sultry Moves Plunging Halter Bodycon Mini Dress
Make sultry moves with all eyes on you in this sexy bodycon mini dress your next night out! The slinky knit fabric offers plenty of stretch for that perfect comfortable fit. The mini-length dress is shaped with a sleeveless plunging V-neckline with a halter strap design, an open back for even more allure, lower back ruching to accentuate your curves, and a bodycon silhouette to flaunt your gorgeous figure. Style with a rhinestone lariat necklace and stiletto heels.
Fit & Features
- Stretchy knit fabric, knit lining
- Plunging V-neckline
- Halter straps
- Open back
- Back ruching
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5659
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Easy And Breezy Lace-Up Midi Dress With Pockets
So effortlessly breezy for any plans, this A-line midi dress will turn heads with a lace-up bust and back detail, while the hidden side pockets are perfect for stashing your phone or lip gloss in.
Fit & Features
- Poplin woven fabric, woven lining
- Sweetheart neckline, lace-up front, stretchy smocked bust
- Spaghetti straps
- Lace-up back, lower zipper and hook-eye closure
- Drop waist seam, hidden side pockets
- A-line silhouette, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6023
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Tropical Fun Rhinestone Pineapple Stud Earrings
Add a touch of tropical fun to your look with these juicy, cute pineapple stud earrings embellished with sparkling rhinestones.
Fit & Features
- Pineapples
- Rhinestone embellished
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000057
Category Name: Vacation Looks
Price: $2.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Major Crush Marble Print Maxi Dress
They'll totally be crushing on you in this alluring abstract marble print maxi dress! It features a strapless straight-across neckline, ruching down one side seam with an adjustable drawstring, a sultry high-cut side slit, and an asymmetric maxi-length hem. The fitted bodice leads to a flowy silhouette. The marble-printed sheer mesh fabric includes a mini-length knit lining. Style with gemstone earrings.
Fit & Features
- Strapless straight-across elastic-banded neckline
- Ruching down one side seam, adjustable drawstring
- High-cut side slit, asymmetric maxi-length hem, lettuce-edge trim
- Fitted bodice, flowy silhouette
- Abstract marble print
- Sheer mesh fabric, mini-length knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5276
Category Name: Vacation Looks
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Three Way Tie Layered Bead Necklace
This layered necklace will win your heart! This stunning necklace features one beaded layer, one dainty beaded chain layer accented with mini clear stones, and one paperclip chain layer, creating a unique and versatile piece. Complete the look in a cute midi dress for a party!
Fit & Features
- Three-row layered design
- One beaded layer
- One beaded chain layer with mini clear stones
- One paperclip chain layer
- Lobster clasp closure
Style Number/Barcode: 07002-1879
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Raise The Bar Wide-Leg Jumpsuit
Raise the bar and strut in this sleeveless jumpsuit featuring a statement design with a plunge halter neckline and an alluring open back. Complete the look with earrings.
Fit & Features
- Smooth knit fabric, plenty of stretch
- Plunging sleeveless halter neckline
- Halter neck ties
- Open back
- Wide-leg silhouette
- Jumpsuit in size small is 58" shoulder to hem with a 13" front rise and a 30" inseam
- Runs true to size
Style Number/Barcode: 06502-2551
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Divine Cutie Tie-Back Ruffled Skater Dress
You'll look positively cute and divine in this short skater dress at brunch or graduations! Designed with a flattering square neckline, adjustable spaghetti straps for the perfect fit, and a tie-back design, this dress is perfect for every girlie. The skater silhouette and ruffled layer add a playful touch, while the short-length hem offers comfort and versatility. Complete the look in strappy mules.
Fit & Features
- Airy woven fabric, sewn-in knit lining
- Adjustable spaghetti straps
- Ruffled
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5733
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Enchanting Look V-Neck Button Down Skater Dress
Your day just got sweeter in this sleeveless skater dress perfect for spring and summer occasions! This V-neck skater dress boasts adjustable spaghetti straps and button closures that allow for the perfect fit while the skater silhouette and short-length hem elevate your style. Complete the look with sandals and sunnies!
Fit & Features
- Woven fabric with lining, no stretch
- Adjustable spaghetti straps
- V-Neckline
- Button down front
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5555
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sparkling Delight Rhinestone Strappy Sandals
These sparkling sandals bring dazzling delight to any look! They're designed in a rhinestone embellished strappy design and a flat sole for comfort.
Fit & Features
- Square toe
- Rhinestone-embellished strappy design
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-000025
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Chic Addition Dainty Stone Threader Earrings
These dainty stone threader earrings will be a chic addition to your jewelry lineup! They feature a long delicate chain threader design accented with small teardrop clear stones at the front and sleek bar detailing at the back. Style with a layered necklace for a trendy luxe vibe.
Fit & Features
- Long dainty chain threader design
- Front teardrop clear stone accents
- Back bar accents
- Rubber stopper
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2039
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Long dainty chain threader design
-
Dreamy Sparkle Celestial Charm Lariat Necklace
This celestial charm lariat necklace will showcase the dreamiest sparkle! It features a dainty chain, an O-ring and toggle closure, a long cascading lariat design, shimmering rhinestones, and sleek moon and star charms for a trendy pop. Pair with stud earrings.
Fit & Features
- Dainty chain
- O-ring and toggle closure
- Rhinestones
- Moon and star charms
- Long lariat design
Style Number/Barcode: 07002-1846
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Dainty chain
-
Poolside Paradise Floral Scrunch Bikini Bottoms
So pretty and made for tanning, these floral bikini bottoms offer a flattering V-shaped low-rise waist and a scrunched thong back that flaunts your curves! Pair with the matching bikini top.
Shop Matching Top: Poolside Paradise Floral Triangle Bikini Top
Fit & Features
- Floral print, stretchy knit fabric
- V-shaped low-rise waist
- Scrunched thong back coverage
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000010
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Stand Out Texture Oval Hoop Earrings
Stand out in these hoop earrings featuring a textured oval design and post-back closures. Perfect for styling your everyday outfits.
Fit & Features
- Textured oval design
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2063
Category Name: Vacation Looks
Price: $3.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Flirty Babe Gingham Print Bandeau Bikini Top
Channel that flirty babe style in this adorable gingham printed bandeau bikini top with a ruffled trim. Pair with the matching bikini bottoms for a sweet and sassy look.
Shop Matching Bottoms: Flirty Babe Gingham Print Side Tie Bikini Bottoms
Fit & Features
- Nylon-blend fabric, high stretch
- Gingham print
- Strapless neckline
- Center bust cutout, tie-front detail
- Ruffled trim
- Thin strappy back design, hook and bar closure
- Runs true to size
Style Number/Barcode: 07104-0718
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Major Head Turner Floral Bodycon Mini Dress
With a sultry strut and this floral mini dress, you'll be a major head turner on vacation or at parties!
Fit & Features
- Floral print, knit-lined stretchy fabric
- Strapless neckline
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000103
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Pretty Chic Floral Chain Necklace
This cute necklace features a dainty flat floral chain design perfect for adding to your layered necklace stack. Complete your pretty chic look with hoop earrings.
Fit & Features
- Dainty flat floral chain
- Back adjustable chain with lobster clasp closure
Style Number/Barcode: 07002-1862
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Romantic Allure Flutter Sleeve A-Line Lace Mini Dress
Indulge in the romantic allure of this lace mini dress with pretty flutter short sleeves and a flattering A-line silhouette. Perfect for shower celebrations, graduations, or brunch!
Fit & Feature
- Lace lined fabric
- Flutter short sleeves
- V-neckline
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4015
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Charmed Sweetness Lace-Up Floral Skater Dress
Charm everyone with your sweetness in this floral skater dress with a flirty lace-up back and a ruffled short hem perfect for any weekend plans.
Fit & Features
- Floral print, woven fabric, bust lining
- V-neckline, wide shoulder straps, padded bra cups
- Lace-up back
- Ruffled skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05102-5622
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
New Moon Star Charm Layered Necklace
Get in touch with your celestial style in this layered necklace featuring a moon and star charm and mini clear stones that put your outfit out of this universe! Complete the look in heels.
Fit & Features
- Two-row layered design
- Moon and star charm
- Mini clear stones
- Lobster clasp closure
Style Number/Barcode: 07002-1870
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale