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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Chic Mood Strappy Faux Leather Block Heel Mules
These strappy faux leather block heel mules will put you in a chic mood! The low-block heels are composed of smooth faux leather material and feature an open square-shaped toe with a thin knotted strappy design across the foot for a trendy look. Include an open back for easy on-and-off styling. Pair these mules with a mini handbag!
Fit & Features
- 3" Block heel
- Faux leather material
- Open square toe
- Knotted strappy design
- Open back
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4760
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Kiss The Sun Tropical Lace-Up Slit Maxi Dress
Sipping a mai tai oceanside has never looked cuter in this tropical maxi dress! Made to turn heads, this maxi dress boasts a sexy lace-up back, form-hugging silhouette that shows off your curves, and a high front slit giving major allure.
Fit & Features
- Tropical print, mesh-lined fabric
- V-neckline
- Spaghetti straps
- Lace-up back
- Form-hugging silhouette, high front slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6103
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunshine Cutie Strapless Ruffle Eyelet Mini Dress
Created for the cuties, this eyelet mini dress is a cute look for shower celebrations or casual parties! Designed to hug your form for a flattering fit, the strapless neckline and ruffled mini hem add a flirty and playful touch.
Fit & Features
- Eyelet fabric, stretchy knit lining
- Strapless neckline
- Form-hugging fit
- Ruffled layer mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000187
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfect Flirt Lace-Up Heeled Thong Sandals
The perfect faux leather sandals for a flirty look with all your sundresses! These exclusive thong sandals showcase a sleek square toe with a thong-style strap, a thin block heel, and thin lace-up straps that let you customize the style. Complete the look with a trendy handbag for any occasion!
Fit & Features
- 3.5" Thin block heel
- Faux leather material
- Square toe, thong strap
- Lace-up straps
- Runs true to size
Style Number/Barcode: 07401-4810
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Mode Buckle Cutout Slit Maxi Dress
A must-have maxi dress for any fashion-forward traveler! Featuring a sweetheart neckline with a trendy buckle accent, a sultry cutout bodice, and a high side slit, this dress will hug your curves and make you feel stylish on your vacation.
Fit & Features
- Texture knit fabric, smooth knit stretchy lining
- Sweetheart neckline with buckle accent
- Spaghetti straps
- Cutout bodice
- High side slit
- Form-hugging fit, maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6082
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Crush On You Sleeveless V-Neck Skater Dress
Everyone will end up with a crush on you in this sleeveless skater dress perfect for beach days or backyard parties! This playful dress features adjustable drawstring shoulder straps and a flattering V-neckline and back design. The fitted waist and skater silhouette create a feminine and flirty look along the short-length hem. Complete the look in heeled sandals.
Fit & Features
- Gauze woven fabric lined with stretchy knit
- Adjustable drawstring shoulder straps
- V-Neckline and back
- Fitted waist, skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5500
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Trend Crew Neck Bodycon Midi Dress
A sleeveless midi dress that'll keep you majorly trendy! Perfect for casual plans or vacations, this midi dress is designed with a flattering crew neckline, bodycon silhouette, and front ruched seam, this dress will accentuate your figure. The front slit adds a touch of drama, while the rib knit fabric offers a sewn-in knit lining for extra coverage. Complete the look with chic sandals and sunnies!
Fit & Features
- Rib-knit stretchy fabric, sewn-in knit lining
- Bodycon silhouette
- Front ruched seam and slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5596
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Juicy Drama Cherry Earrings
These cherry earrings know how to steal the spotlight. Serve juicy drama with every head turn, whether you're posting or partying!
Fit & Features
- Cherries with sleek stems
- Pull-through design
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000098
Category Name: Vacation Looks
Price: $9.90
Availability: In Stock
Available Color: BLOOD, RED
Available Size: NS
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Finders Keepers V-Neck Tie Midi Dress
Once you find this sleeveless midi dress you'll want to keep it! Perfect for semi-formal occasions, this midi dress will make you feel chic and effortless. Designed with an adjustable V-neckline with a bust tie, sleek spaghetti straps, and a flattering curve-hugging silhouette that exudes charm. Complete the look with a bolero shrug sweater and strappy stilettos!
Fit & Features
- Woven fabric, no stretch
- Spaghetti straps
- Adjustable bust tie
- Curve-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-5551
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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High Intentions Sleeveless Knit Mini Dress
Take your wardrobe to the next level in this little black dress perfect for day or night plans! This mini dress boasts a sleeveless high square neckline and spaghetti straps for a chic and modern look. The bodycon silhouette hugs your curves, while the mini-length hem adds a touch of flirtatiousness. The lightweight knit fabric offers a moderate stretch. Complete the look in a trendy crop jacket, mules, and a purse!
Fit & Features
- Knit fabric with moderate stretch
- High square neckline
- Spaghetti straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1881
Category Name: Vacation Looks
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feeling Bliss Rib Knit Pajama Pants
Experience comfort and bliss in these soft pajama pants! Its elasticized drawstring high-rise waist, wide-leg silhouette, and soft rib knit fabric ensure a cute and cozy lounge. Complete the look with the matching pajama top.
Shop Matching Top: Feeling Bliss Rib Knit Pajama Tank Top
Fit & Features
- High-rise elasticized drawstring waist
- Wide-leg silhouette
- Soft rib knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07103-0955
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- High-rise elasticized drawstring waist
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Sunny Thoughts Sleeveless Cutout Crochet Maxi Dress
Get summer vibes in an instant wearing this crochet maxi dress perfect for vacation or strolling the boardwalk! Featuring a flattering square neckline, spaghetti straps, and a stunning cutout back with an adjustable drawstring insert and a front slit for movement along the maxi-length silhouette. Complete the look with sunglasses and sandals.
Fit & Features
- Crochet knit fabric lined with stretchy knit
- Spaghetti straps
- Square neckline
- Cutout back, adjustable drawstring insert
- Front slit
- Maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-5742
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pretty Blooms Floral Mesh Halter Maxi Dress
Showcase your beauty in this lined mesh maxi dress accented with a large floral print for a pretty vibe. It features a sleeveless cowl neckline, halter tie-back spaghetti straps with beaded detailing, an open back with lower tie-back straps, and a maxi-length hem with a form-hugging fit to highlight your curves.
Fit & Features
- Sheer mesh fabric with knit lining
- Large floral print pattern
- Cowl neckline
- Halter tie-back spaghetti straps, beaded details
- Open back, lower tie-back spaghetti straps, beaded details
- Maxi-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5988
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Western Moves Sweetheart Denim Skater Mini Dress
Show off your Western style in this denim skater mini dress for dancing in the desert at festivals or concerts!
Fit & Features
- Denim fabric, stretchy knit lining
- Sweetheart neckline, underwire bust
- Adjustable spaghetti straps
- Back zipper closure
- Bodycon bodice
- Skater chiffon lace trim mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6018
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunny Sweet Floral A-Line Mini Dress
Sunny sweet will be your vibe in this cute floral mini dress designed with a strapless neckline, ruching, and a hanky hem A-line silhouette.
Fit & Features
- Knit fabric, high stretch
- Small floral print
- Strapless straight neckline
- Ruching
- Drop waist
- Mini-length hanky hem, A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000008
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Style Acrylic Bangle Bracelet
Low-effort, high-impact vibes. This acrylic bangle bracelet is your go-to for adding a bold, minimal twist to any look—stack it up or wear it solo for instant cool.
Fit & Features
- Acrylic material
- Thick bangle silhouette
- Slip-on design
Style Number/Barcode: 07003-000125
Category Name: Vacation Looks
Price: $2.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Let's Get Away Open Back Sleeveless Crop Top
This sleeveless crop top is exactly what you need for a casual vacay or weekend look! Made with double-lined brushed knit fabric, this top is both soft and durable. The square neckline and open-back twist design create a trendy look, while the fitted crop hem provides a flattering silhouette. Complete the look in jean shorts and sandals!
Fit & Features
- Double-lined brushed knit stretchy fabric
- Twist open back design
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-5250
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Romance Rules Lace-Up Lace Tunic Top
Get swept off your feet with the romantic allure of this lace tunic top, designed with a pretty lace-up front and flowy silhouette with a cute ruffle trim.
Fit & Features
- Sheer lace fabric, bust knit lining
- V-neckline, adjustable spaghetti straps
- Lace-up front design
- Flowy silhouette
- Ruffled trim, open front slit design
- Longline hem
- Runs true to size
Style Number/Barcode: 06003-000070
Category Name: Vacation Looks
Price: $49.90
Availability: Out of Stock
Product Badge:- Ships Free
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Breezy Weekend Short Sleeve Button Up Denim Romper
From coffee shops to running errands, you'll live in this sweet denim romper all weekend! With its collar neckline, form-hugging fit, and short-length hem, this short sleeve romper is perfect for any adventure. And with flap pockets and button-up front closures, you can keep stylish. Complete the look with flat sandals and a crossbody bag!
Fit & Features
- Denim fabric, minimal stretch
- Collar neckline
- Button-up front closures
- Flap pockets
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06603-0383
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ready For Anything Puffer Tote Bag
Versatile and ready for anything, this puffer tote bag keeps your essentials organized and your look on-trend! It's designed with top handles and an adjustable crossbody strap for versatile wear. The top snap-button closure leads to a spacious and lined interior with side pockets to hold your phone or other loose items and a secure zipper pocket perfect for stashing cash or cards. Complete the look in a casual jumpsuit or romper for weekend plans or travel!
Fit & Features
- Insulated puffer material
- Top handles
- Adjustable crossbody strap
- Top snap-button closure
- Spacious interior, lined, three pockets
Style Number/Barcode: 07203-2003
Category Name: Vacation Looks
Price: $10.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Enchanting Charm Butterfly Rhinestone Lariat Necklace
Add an enchanting charm to your look with this pretty butterfly rhinestone lariat necklace! It features a two-row design with a rhinestone chain layer and a dainty ball chain layer accented with a rhinestone-embellished butterfly charm, a cascading ball chain lariat, and a sleek rhinestone-adorned bar charm. Style with a chic ring set.
Fit & Features
- Two-row layered design
- Rhinestone chain layer
- Ball chain layer
- Rhinestone-embellished butterfly charm
- Ball chain lariat, rhinestone-embellished bar charm
- Back adjustable chain with lobster clasp closure
Style Number/Barcode: 07002-1766
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wanderlust Paisley Print Knit Flare Pants
You'll be a wanderlust beauty in these paisley print flare pants, perf for creating a dreamy desert festival look! The soft and stretchy brushed knit fabric features a bohemian-inspired paisley print pattern for those effortlessly cool vibes. The high waist has an elastic band for comfortable wear. The hip-hugging fit continues through the leg, leading to a trendy flared hem. Style with a crop top and ankle booties.
Fit & Features
- Stretchy brushed knit fabric
- Paisley multi-print pattern
- High-rise elasticized waist
- Hip-hugging fit
- Flared hem
- Runs true to size
Style Number/Barcode: 06502-2439
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend Cozy Henley Button Skinny Leg Jumpsuit
This henley button skinny-leg jumpsuit is perfect for a cozy day out. Made from stretchy seamless rib knit fabric, it offers both comfort and style. The scoop neckline features snap-button closures for added detail while the form-hugging fit and skinny-leg design create a flattering silhouette. Complete the look in platform sneakers and a crop jacket!
Fit & Features
- Seamless stretchy rib knit fabric
- Snap-button closures
- Form-hugging fit
- Skinny-leg design
- Runs true to size
Style Number/Barcode: 07109-0387
Category Name: Vacation Looks
Price: $4.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Such A Cutie Halter Ruffle Mini Dress
Make this halter mini dress a staple this season! The form-hugging silhouette accentuates your curves in all the right places, while the playful ruffled hem adds flirty movement. Style with strappy heels.
Fit & Features
- Texture knit fabric, moderate stretch
- Cowl neckline
- Spaghetti straps with hoop inserts
- Form-hugging fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000132
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free