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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Check Me Out Puff Sleeve Cutout Gingham Crop Top
You'll check yourself in every mirror in this sweet gingham crop top perfect for spring to summer fun! This gingham crop top will surely turn heads, featuring puff sleeves, a cutout bust, and an open back with tie closure. Complete the look in high-rise denim shorts.
Fit & Features
- Gingham pattern, woven lined fabric, no stretch
- Sweetheart neckline with cutout
- Open back, tie closure
- Cropped hem
- Runs true to size
Style Number/Barcode: 06003-2368
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunshine Romance Floral Babydoll Dress
Indulge in the romantic allure of this floral dress for dressy events! With delicate ruffled shoulder straps and a charming babydoll silhouette, this dress offers a flirty and feminine look.
Fit & Features
- Floral print, chiffon fabric
- Square neckline
- Ruffled shoulder straps
- Babydoll silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3467
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fabulous Destination Tropical Cowl Neck Maxi Dress
Look fabulous heading to your destination in this tropical maxi dress for the cutest look on the island or beach resort! The cowl neckline creates a flattering drape and spaghetti strap tie while the low cowl back adds a touch of allure. The flowy maxi silhouette will make you feel like you're on a tropical escape! Complete the look in sunnies.
Fit & Features
- Tropical palm print, stretchy knit fabric
- Cowl neckline
- Low cowl back, spaghetti strap tie
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5727
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Turn Up The Heat One-Shoulder Cutout Midi Dress
Turn up the heat in this sultry knit midi dress designed with a one-shoulder neckline, front cutouts, sleek O-ring accents, and a high-cut side slit. The bodycon fit will highlight your gorgeous curves.
Fit & Features
- Smooth knit fabric with knit lining, high stretch
- Sleeveless asymmetric one-shoulder neckline, gold metal O-ring accent, tank strap
- Dual front cutouts under the bust and above the waist, gold metal O-ring accent
- Ruching
- Midi-length hem, thigh-high side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000117
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fun Vibes Floral Straw Flat Sandals
The fun and cute vibes of these sandals will have you living in them all season! They feature a sleek square toe with a floral patterned straw band for a trendy touch and a comfortable flat sole. Complete the look with a cute mini handbag.
Fit & Features
- Square toe
- Floral patterned straw band
- Flat sole
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07404-1159
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Jetset Babe Tropical Print Belted Maxi Dress
Jetset to somewhere fabulous in this tropical print maxi dress! The flattering belted waist cinches your silhouette while hidden side pockets add convenience. A sultry side slit creates movement for a trendy look.
Fit & Features
- Tropical multi-print, woven fabric
- Strapless neckline
- Belted waist
- Hidden side pockets
- Flowy maxi silhouette, side slit
- Runs true to size
Style Number/Barcode: 05102-000112
Category Name: Vacation Looks
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Match My Energy Eyelet Skater Dress
This adorable dress will have you feeling cute and carefree for any fun plans! The strapless neckline, ruffled skater silhouette, and eyelet print add a touch of playfulness to your everyday look.
Fit & Features
- Eyelet fabric, sewn-in knit lining
- Strapless neckline
- Strappy back
- Ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000108
Category Name: Vacation Looks
Price: $9.97 $65.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Texas Sun Frayed Straw Panama Hat
Designed to keep you cool and stylish under the sun, this panama hat features a frayed straw design with a wide brim and inner adjustable strings for a snug fit. Complete the look in cute cowboy boots for your next trip.
Fit & Features
- Frayed straw design
- Wide brim
- Inner adjustable strings
Style Number/Barcode: 07302-1631
Category Name: Vacation Looks
Price: $4.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Falling For You Tropical Floral Slit Maxi Dress
Get the golden hour glow in this tropical floral maxi dress while on vacation! Featuring a chic square halter neckline and a form-hugging fit with a high side slit, this dress beautifully accentuates your silhouette.
Fit & Features
- Tropical floral print, mesh-lined fabric
- Square halter neckline, adjustable spaghetti straps
- Criss cross back
- Form-hugging silhouette
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6113
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feeling Chic Thong Square Toe Heels
From daytime outings to nights out, these thong heels are perfect for dressing up any look for every occasion!
Fit & Features
- 2" short kitten heel
- Square toe
- Thin thong toe strap
- Cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-000490
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: CAMEL, BLACK, LIGHT, BLUE, WINE, PINK, TAN
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 10, 9
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Chic Alignment Celestial Layered Necklace
All the stars and planets aligned to inspire this celestial layered necklace! It features dual dainty chain links with a rhinestone moon and star charm. Complete the look in a bustier and jeans for going out!
Fit & Features
- Dual dainty chain links
- Rhinestone moon and star charms
- Lobster clasp closure
Style Number/Barcode: 07002-1830
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Sweet Floral And Plaid Patchwork Mini Dress
Create the perfect weekend look in this oh-so-sweet mini dress designed with a floral and plaid patchwork pattern. The crochet bust trim and tie-front detail are dainty details you'll adore.
Fit & Features
- Woven fabric, no stretch
- Ditsy floral and plaid patchwork pattern
- Sleeveless sweetheart neckline, crochet trim and tie-front detail, ruched bust
- Adjustable spaghetti straps
- Hidden back zipper, hook-eye closure
- Mini-length hem, fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-000178
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Covetable Layered Rhinestone Charm Necklace Set
Elevate your looks by pairing them with this layered rhinestone charm necklace set! It features a snake chain choker, a dainty chain with a sparkly rhinestone charm to add a glam effect, and a flat dainty chain for a trendy vibe. Complete the look in a strapless dress for dinner and drinks!
Fit & Features
- Layered necklace set
- Snake chain choker
- Dainty chain with rhinestone charm
- Flat dainty chain
- Back adjustable chains with lobster clasp closures
Style Number/Barcode: 07002-1839
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Darling Ditsy Floral V-Neck Mini Dress
This ditsy floral mini dress will have you dreaming of sunshine days! Flaunt your figure with the bodycon fit of this dress showcasing a flattering V-neckline, dainty spaghetti straps, a tie-front bust for added detail, and a mini-length hem on ditsy floral print mesh fabric. Complete the look in sandals and a mini tote bag.
Fit & Features
- Ditsy floral print
- Mesh fabric lined with stretchy knit
- Spaghetti straps
- Slit accent
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5571
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Shine On Me Layered Disc Belly Chain
Just a lil sparkle to catch the light (and compliments). This delicate layered belly chain brings the shine with dainty disc details and major stacking potential.
Fit & Features
- Layered chain silhouette
- Mini disc charms
- Adjustable lobster clasp closure
Style Number/Barcode: 07002-000098
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
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Sitting In The Sun Floral Babydoll Mini Dress
So charming for sunny days, this floral babydoll mini dress is fit for frolicking downtown to brunch or attending a shower!
Fit & Features
- Floral print, eyelet woven fabric, chiffon lining
- Square neckline
- Wide adjustable shoulder straps
- Stretchy smocked bust
- Flowy ruffled babydoll silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4002
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Head-Turning Flirt Bodycon Mini Dress
A bodycon mini dress that makes the perfect foundation to create flirty looks!
Fit & Features
- Rib knit fabric, sewn-in knit lining, moderate stretch
- Strapless neckline
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000086
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Whimsical Touch Pearl Flower Strap Cork Wedges
Hello 2024 brides! Add a whimsical touch to your bridal looks with these pearl flower strap cork wedges perfect for engagement parties, bachelorettes, or rehearsal dinners! Made with smooth faux leather, they feature an open almond-shaped toe, a toe strap accented with chic chiffon flowers with center faux pearl detailing, thin adjustable ankle and heel straps, and a tall cork wedge heel for added lift and support. Style with elegant jewelry.
Fit & Features
- 4" Cork wedge heel
- Faux leather upper
- Open almond toe
- Toe strap with chiffon flowers with faux pearl details
- Adjustable ankle and heel straps, buckle closure
- Padded insole
- Runs true to size
Style Number/Barcode: 07406-0340
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Romance Dreamer Strapless Bodycon Lace Mini Dress
You'll be graced by lace in this bodycon mini dress as the lovely bride-to-be, birthday cutie, or graduate girlie!
Fit & Features
- Laced lined fabric
- Strapless neckline
- Bodycon silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3824
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunny Days Square Neck Tie-Back Skater Short Dress
Sunny days pair perfectly with this skater short dress for casual occasions or day dates! Made from lightweight cotton, this dress boasts a square neckline and elasticized cap sleeves for a perfectly feminine touch. The smocked bodice and tie-back waist ensure a flattering fit, while the tiered skater silhouette adds a playful flair. Complete the look with sandals, sunglasses, and a purse for a cute style!
Fit & Features
- Lightweight cotton fabric with woven lining
- Stretchy smocked bodice
- Tie-back waist
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5417
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Major Charmer Ditsy Floral Strapless Mini Dress
Charm them with your adorable style in this lined eyelet knit mini dress with the cutest ditsy floral print. The form-hugging fit will highlight your curves.
Fit & Features
- Sheer eyelet knit fabric with knit lining, high stretch
- Ditsy floral print
- Strapless straight neckline
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-6046
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet But Savage Lace Floral Leopard Mini Dress
Giving major heartbreaker energy! This flirty A-line mini dress hugs you just right with its mesh fabric and mixed prints. Pair it with heels or a chunky boot—your vibe, your rules.
Fit & Features
- Floral leopard print, mesh fabric, stretchy knit lining
- Sweetheart neckline, adjustable spaghetti straps
- Lace underwire bust with bow
- Back zipper and hook-eye closure
- Princess seams down the front
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000267
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
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Majorly Tropical Plunge Halter Wide-Leg Jumpsuit
Grab some shades and throw on this tropical plunge halter wide-leg jumpsuit for majorly vacay vibes on your getaway or weekend escape! Featuring a sultry plunge halter neckline with button closures and an open tie-back design, this jumpsuit effortlessly is a sexy style. The wide-leg silhouette and tropical palm print on knit fabric add a touch of tropical flair to any look. Complete the look with sunglasses and a floppy hat!
Fit & Features
- Tropical palm print, knit fabric, bust lining, stretchy
- Plunge neckline with button closures
- Open tie back design
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-2455
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wild Thing Zebra Print Statement Earrings
Hey there wild thing! You'll be looking fierce in these zebra statement earrings featuring a textured post and a zebra-printed shell with glitter accents. Includes a post-back closure. Complete the look in a trendy denim jumpsuit for any occasion!
Fit & Features
- Textured post
- Zebra print shell with glitter accents
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2035
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free