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.
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Vacation Looks
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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.
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Beachy Beauty Seashell Charm Anklet Set
Create a coastal chic look radiating effortlessly glam vibes with this beachy anklet set! It features three dainty anklets including a small chain-link design, a beaded chain-link design, and a trendy paperclip chain accented with rhinestones, faux pearls, and seashell charms. Style with strappy sandals.
Fit & Features
- Three-pack anklet set
- Small chain
- Beaded chain
- Paperclip chain with rhinestones, faux pearls, and seashell charms
- Back adjustable chains, lobster clasp closures
Style Number/Barcode: 07003-0556
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Cherry Charm Necklace
Make your look sweet for summer with this cherry charm necklace featuring a delicate chain with a lobster clasp closure. Style this necklace with a summer dress for a backyard BBQ or carnival!
Fit & Features
- Cherry charm
- Delicate chain
- Lobster clasp closure
Style Number/Barcode: 07002-1806
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bohemian-Chic Geometric Striped Halter Maxi Dress
Channel a bohemian chic vibe with this breezy halter maxi dress perfect for summer. The lightweight woven fabric showcases a geometric striped print in stylish neutral hues. The long dress features a sleeveless plunging V-neckline, halter spaghetti straps that can be crossed in the front for a trendy look, and a tie-back design at the neck. The alluring open back leads to lower tie-back straps and a lower cutout accent. You'll love the hidden side pockets and high side slit on the effortless, flowy silhouette. Complete the look with strappy sandals.
Fit & Features
- Geometric striped print
- Woven fabric, no stretch
- Plunge V-neckline, halter spaghetti straps, tie-back design
- Open back, lower tie-back straps, lower cutout
- Side pockets
- Side slit, flowy fit
- Runs true to size
Style Number/Barcode: 05102-5842
Category Name: Vacation Looks
Price: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spring Has Sprung Floral Woven Skater Dress
Let your beauty bloom in this adorable floral woven skater dress! The lightweight lined woven fabric is accented with a dainty floral print for the sweetest allure. The short dress features a sleeveless sweetheart neckline with a padded bust and structured underwire for support. The corset-style bodice will snatch your waist and highlight your bust with a tie-front detail. The thin smocked shoulder straps lead to a smocked back design for added stretch with a zipper closure. The high waist flows out to a short skater skirt with a trendy bubble hem and a fit and flare silhouette. Pair with platform heels for the cutest party look!
Fit & Features
- Floral woven fabric with knit lining, minimal stretch
- Sleeveless sweetheart neckline, padded bust with underwire
- Thin tank shoulder straps
- Smocked back design, zipper and hook and eye closure
- Corset bodice, tie-front detail, high waist seam
- Short skater skirt with bubble hem, fit and flare silhouette
- Runs true to size
Style Number/Barcode: 05101-3187
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Instantly Chic Oversized Square Sunglasses
These fabulous shades will instantly elevate your look and make it all the more chic! The sunglasses feature an oversized square slightly angled design, a sleek plastic frame and arms, built-in nose pads for support, and tinted lenses. Style with classic hoop earrings.
Fit & Features
- Oversized square-shaped design
- Plastic frame and arms
- Built-in nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1082
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simply Rad Flat Top Rectangle Sunglasses
Unlock a rad and cool vibe in these cute sunglasses! They feature a trendy flat top design, rectangular plastic frames, and tinted lenses to help protect your eyes from the sun. Complete the look with sleek hoop earrings for any occasion!
Fit & Features
- Flat top
- Rectangular plastic frames
- Tinted lenses
Style Number/Barcode: 07008-1084
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Perfection Striped Crochet Straw Bucket Hat
Create perfect summertime 'fits with this striped crochet straw bucket hat! Made with lightweight crochet straw material, this adorable hat features natural and green hues woven together to create the cutest striped pattern. Offers a flexible brim for effortless styling. Pair this bucket hat with a breezy crochet dress and lace-up sandals!
Fit & Features
- Crochet straw material
- Striped woven design
- Flexible brim
Style Number/Barcode: 07302-1551
Category Name: Vacation Looks
Price: $4.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Link Up Luxe Chain Necklace
Bold neck, big flex. This chunky chain is your shortcut to instant cool-girl status. Layer it up or let it shine solo—it’s that versatile power piece every jewelry box needs.
Fit & Features
- High-shine metal with luxe finish
- Chunky link chain silhouette
- Lobster clasp closure for a secure fit
Style Number/Barcode: 07002-000037
Category Name: Vacation Looks
Price: $2.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Getaway Sleeveless Nylon Cargo Jumpsuit
This sleek nylon cargo jumpsuit is essential for your next casual getaway! Designed with a lightweight smooth nylon-blend fabric, it features a square neckline with adjustable spaghetti straps for a customized fit. The high waist is detailed with belt loops and a faux button accent, leading to multiple pockets down the leg for a trendy design. The hem features adjustable drawcords to create a cinched jogger silhouette. Style this jumpsuit with strappy sandals.
Fit & Features
- Smooth nylon-blend woven fabric, no stretch
- Sleeveless square neckline with adjustable spaghetti straps
- High waist with belt loops and faux front button
- Hidden back zipper
- Dual front pockets, dual faux back pockets, cargo side pockets
- Relaxed silhouette, adjustable drawcords at the hem
- Runs true to size
Style Number/Barcode: 06302-0816
Category Name: Vacation Looks
Price: $11.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cool Icon Chain-Link Rectangle Sunglasses
Give off major cool girl vibes in these chain-link rectangle sunglasses. They feature a trendy rectangular-shaped design with a sleek plastic frame, shiny metal arms with a chain-link design, built-in nose pads for support, and tinted lenses. Style these iconic sunnies with hoop earrings.
Fit & Features
- Rectangular-shaped design
- Plastic frame
- Metal arms with chain-link design
- Built-in nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1074
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Nice Gal Beaded Straw Cowboy Hat
Tip this straw cowboy hat looking like the nicest gal around town! Featuring a beaded faux leather band with a string bow tie, this hat adds a boho chic look. The curved wide brim not only provides stylish sun protection but also adds a playful flair. Made with straw material and an elasticized inner band for a comfortable and secure fit. Complete the look in cowboy boots.
Fit & Features
- Straw material
- beaded faux leather band with string bow tie
- Curved wide brim
- Inner elasticized band for a snug fit
Style Number/Barcode: 07302-1645
Category Name: Vacation Looks
Price: $12.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Miss America Baseball Cap
Show your patriotic spirit in this cute and trendy baseball cap featuring a curved wide brim to help shade your eyes, a front embroidery that reads "Miss America" and an adjustable back strap for a snug fit. Complete the look in a denim romper for a backyard BBQ.
Fit & Features
- Curved wide brim
- Front embroidery that reads "Miss America"
- Adjustable back strap
Style Number/Barcode: 07302-1639
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Staple Linen Strap Espadrille Wedges
A chic summer staple, these linen strap espadrille wedges will elevate your summer 'fits! They feature an open almond-shaped toe with a wide linen toe strap, linen criss-cross adjustable ankle straps, an espadrille heel strap, and a tall espadrille wedge heel to give you that stylish height with a comfortable fit. Pair with a flowy skater dress!
Fit & Features
- 5" Espadrille wedge heel
- Open almond toe
- Wide linen toe strap
- Linen criss-cross adjustable ankle straps
- Espadrille heel strap
- Runs true to size
Style Number/Barcode: 07406-0348
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vineyard Gal Floral Woven Skater Dress
This vintage-inspired floral woven dress is perfect for vineyard weddings, wine tastings, and daytime soirees! The skater dress features adorable short puff sleeves, a sweetheart neckline with a bust tie, a lace-up back design, and a tiered fit-and-flare skater silhouette with a short hem. The lined woven fabric showcases a vintage floral print pattern. Style this short dress with on-trend strappy mules.
Fit & Features
- Short puff sleeves
- Sweetheart neckline, bust tie
- Lace-up back design, tie closure
- Tiered fit-and-flare skater silhouette
- Short-length hem
- Vintage floral print, lined woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 05101-2966
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Leaving An Impression Striped Ribbed Knit Midi Dress
Leave an impression in this striped knit midi dress everywhere you go! With adjustable spaghetti straps, a sweetheart neckline, a cutout bust, and a form-hugging fit, this dress is both stylish and comfortable. The dual side slits add a trendy flair to the midi-length hem. The ribbed knit fabric offers plenty of stretch. Complete the look in sandals and sunglasses!
Fit & Features
- Striped pattern, stretchy ribbed knit fabric
- Adjustable spaghetti straps
- Sweetheart neckline
- Cutout bust
- Form-hugging fit
- Dual side slits
- Runs true to size
Style Number/Barcode: 06005-1976
Category Name: Vacation Looks
Price: $19.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pop Of Cute Straw Faux Leather Flat Sandals
Add a pop of cute to your outfit in these faux leather flat sandals for everyday styling! These sandals are the perfect combination of comfort and style, featuring a sleek square toe and a trendy straw band with notch cutouts on faux leather material. Complete the look with a chic pair of sunglasses.
Fit & Features
- Square toe
- Straw band with notch cutouts
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1231
Category Name: Vacation Looks
Price: $12.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Romantic Spot Strapless Floral Chiffon Romper
The perfect romantic floral chiffon romper for summer date nights or soirees! Made from delicate ditsy floral and polka dot printed chiffon fabric, this romper exudes a playful and feminine charm. The strapless neckline and tie-back design offer a perfect fit while the flowy short-length hem adds a touch of elegance. Complete the look with high heels.
Fit & Features
- Ditsy floral and polka dot print
- Chiffon fabric lined with woven fabric
- Strapless neckline
- Back zipper and hook-eye closure
- Flowy short-length
- Runs true to size
Style Number/Barcode: 06403-0546
Category Name: Vacation Looks
Price: $20.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Always Admired Scoop Neck A-Line Mini Dress
You'll always admire having this sleeveless mini dress for dressing up or down! Made from lined stretchy rib knit fabric, this dress hugs your curves in a flattering A-line silhouette. The scoop neckline and thin spaghetti straps add a flattering look. Style with a cute jacket and your favorite sneakers!
Fit & Features
- Stretchy rib knit fabric, full knit lining
- Spaghetti straps
- Curve-hugging, A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5652
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweeter Than Floral Short Sleeve Tie-Back Romper
What could be sweeter than you in this floral romper? Play up your style in this must-have romper for the spring-to-summer season. The ruffle trim puff sleeves add a whimsical touch, while the form-hugging silhouette and tie-back detail create a flattering fit. With a short-length hem and a square neckline, this romper is flattering for any occasion! Complete the look in heeled sandals and hoop earrings.
Fit & Features
- Floral print, woven fabric with full woven lining
- Tie-back design
- Back zipper and hook-eye closure
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06403-0441
Category Name: Vacation Looks
Price: $19.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Main Frame Oversized Square Sunglasses
These oversized sunglasses will be your main pick for a casual-cute style all season long! They feature an oversized plastic square frame with gold trim, built-in nose pads, tinted lenses, and a comfortable fit. Complete the look with sleek jewelry.
Fit & Features
- Oversized plastic square frames
- Gold trim
- Built-in nose pads
- Tinted lenses
- Comfortable fit
- 100% UV protection
Style Number/Barcode: 07008-1075
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Classic Trendsetter Rectangle Sunglasses
A classic trendsetter like yourself needs a pair of iconic rectangle sunglasses as an everyday staple. These sunnies feature a small rectangular-shaped design with a plastic frame and arms, built-in nose pads, and tinted lenses. Style with a chic shoulder bag.
Fit & Features
- Small rectangular-shaped design
- Plastic frame and arms
- Built-in nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1098
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bow And Tell Floral Slide Sandals
Serving garden party glam with zero effort. These floral bow slides are playful, comfy, and practically begging for a vacay moment (or brunch pic).
Fit & Features
- Round toe
- Bow strap
- Flat sole
- Floral print
- Faux leather insole
- Runs true to size
Style Number/Barcode: 07404-000015
Category Name: Vacation Looks
Price: $22.90
Availability: In Stock
Available Color: MULTI
Available Size: 5.5, 6, 6.5, 7, 7.5, 8
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Looking Sleek Square-Frame Sunglasses
Accessorize your fave 'fits with these square-frame sunglasses for a sleek and chic vibe. The sunnies feature a classic square-shaped design with a plastic frame and arms, built-in nose pads, and tinted lenses. Style with hoop earrings.
Fit & Features
- Square-shaped design
- Plastic frame and arms
- Built-in nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1076
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tuscan Charm Strapless Slit Eyelet Maxi Dress
You'll be so charming in Tuscan wearing this eyelet maxi dress as the stunning new bride or chic traveler! The eyelet fabric adds a touch of delicacy, making it the perfect dress for any occasion. With a form-hugging fit and a high-side slit, this dress exudes confidence and elegance! Complete the look with earrings.
Fit & Features
- Eyelet fabric, sewn-knit lining, minimal stretch
- Strapless neckline
- High side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5637
Category Name: Vacation Looks
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale