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 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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Heart Skip Satin Slip Dress
The dress that makes every mirror check last a little longer. Delicate lace details, a sleek satin finish, and an asymmetrical hem give this slip dress an effortless allure that's polished and unexpected.
Fit & Features
- Silky satin fabric
- Lace trim V-neckline
- Adjustable spaghetti straps
- Low-back detail
- Curve-hugging silhouette
- Lace trim asymmetrical hem with a side slit
- Runs true to size
Style Number/Barcode: 05101-001476
Category Name: Vacation Looks
Price: $46.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
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Euro Summer Satin Floral Scarf
Your outfit just found its finishing touch. This satin floral scarf brings that effortless Euro summer feel—tie it in your hair, around your neck, or on your bag for an instant upgrade.
Fit & Features
- Silky satin fabric
- Floral print design
- Multiple ways to style and wear
Style Number/Barcode: 07305-000100
Category Name: Vacation Looks
Price: $15.90
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Whisper Mesh Lace Corset Top
This one feels straight out of a saved summer outfit board. The mesh lace corset top combines sheer floral texture with contour seams and a tie-front neckline for a soft, sculpted fit that still feels effortless.
Fit & Features
- Sheer mesh-lined fabric with floral lace overlay
- Off-the-shoulder neckline with cap sleeves
- Tie-front neckline detail
- Hook-and-eye front closure
- Adjustable lace-up back detail
- Runs true to size
Style Number/Barcode: 06001-000607
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Polished Move Twill Hot Shorts
Short, sleek, and booked. These twill hot shorts bring a fitted high-rise silhouette with buttoned pocket details that make even your last-minute outfit look polished and planned.
Fit & Features
- Twill fabric
- High-rise waist, belt loops
- Front button and hidden zipper closure
- Front buttoned pockets
- Fitted silhouette
- Runs true to size
Style Number/Barcode: 06303-000062
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
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Ruffle Me Up Lace Halter Mini Dress
Serving flirty femme vibes—this lace mini dress with tiered ruffles is giving soft glam perfection. The halter neckline and curve-hugging fit make it your new go-to for bridal celebrations and dressy brunch plans.
Fit & Features
- Lace-lined fabric
- Halter V-neckline
- Bodycon silhouette
- Tiered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001181
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: WHITE
Available Size: M, L
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Perfectly Pretty Tie Back Chiffon Babydoll Dress
Perfectly pretty in the sweetest babydoll silhouette, this mini-length dress offers an adorable tie-back detail and ruffled trim hem for an effortless flounce with every step! Style with heels for shower celebrations or graduation.
Fit & Features
- Chiffon-lined fabric
- Sweetheart neckline, twist bust, padded bra cups
- Adjustable spaghetti straps
- Tie-back detail
- Babydoll silhouette
- Ruffled trim mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000495
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Whispered Romance Lace Mini Dress
This one feels light, romantic, and a little bit magical. The delicate lace, ruffled hem, and halter neckline create a flirty silhouette that’s perfect for bridal celebrations, special date nights, or any moment worth dressing up for.
Fit & Features
- Lace fabric with partial lining
- Halter V-neckline with adjustable tie-back
- Ruched lace bodice with center ruffle detail
- Open back design
- Fitted silhouette through the waist and hips
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000291
Category Name: Vacation Looks
Price: $20.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: L
Product Badge:- Sale
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Dreamy Eyelet Ruffle Mini Dress
This sweet eyelet dress brings soft romance with a playful twist. The square neckline, puff sleeves, and tiered ruffle skirt create a flattering A-line silhouette that feels effortlessly feminine. Perfect for brunch dates, garden parties, or sunny day plans.
Fit & Features
- Eyelet fabric, knit lining
- Square neckline
- Short puff sleeves
- Fitted bodice
- Drop waist A-line silhouette
- Tiered ruffle mini hem
- Runs true to size
Style Number/Barcode: 05102-000493
Category Name: Vacation Looks
Price: $19.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: M, L
Product Badge:- Sale
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Twirl Plans Skater Mini Dress
This is the dress you reach for when the invite says dress up. The skater mini silhouette with a strappy back and flowy godet panels gives you that twirl-worthy, all-eyes-on-you feel.
Fit & Features
- Knit-lined stretchy fabric
- V-neckline
- Spaghetti straps
- Strappy back design
- Skater silhouette, godet panels for extra flare
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000976
Category Name: Vacation Looks
Price: $28.00 $39.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
Product Badge:- Sale
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Sunny Days Crochet A-Line Mini Dress
Booked, packed, and already planning the outfit. This A-line mini dress with a crochet bust overlay and lace-up back brings that effortless Euro summer vibe with a flirty, easy fit.
Fit & Features
- Linen-like fabric, smooth woven lining
- V-neckline, crochet bust overlay, tie bust front
- Spaghetti straps
- Strappy tie-back design
- Princess seam, A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000494
Category Name: Vacation Looks
Price: $35.00 $49.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- Sale
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City Darling Lace Skater Mini Dress
Last-minute invite? Already handled. This lace tube skater dress hugs through the bodice with a flirty flare skirt that’s made for graduations, bridal celebrations, and every dressy plan in between.
Fit & Features
- Lace fabric with lining
- Strapless tube neckline
- Fitted skater silhouette
- Flowy mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001171
Category Name: Vacation Looks
Price: $29.97 $64.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: L
Product Badge:- Sale
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All Eyes On You Sequin Floral Top
Subtle? Not today. This sequin floral spaghetti strap top catches the light from every angle with a low back tie detail that keeps things barely there and unforgettable—perfect for birthdays, date nights, and any excuse to dress up.
Fit & Features
- Lightweight fabric with sequin floral embellishment
- V-neckline with spaghetti straps
- Open lace-up back with tie closure
- Cropped silhouette
- Runs true to size
Style Number/Barcode: 06003-000212
Category Name: Vacation Looks
Price: $36.90
Availability: Out of Stock
Product Badge:- Ships Free
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A Bit Flirty Lace Halter Dress
This lace mini dress gives you that effortless twirl moment with a light, easy fit that feels made for bridal celebrations, birthdays, graduations, and every dressed-up moment.
Fit & Features
- Lace-lined fabric
- Halter neckline with tie straps
- A-line silhouette
- Layered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000950
Category Name: Vacation Looks
Price: $20.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: XS, L
Product Badge:- Sale
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Garden Party Glam Floral Clutch
The kind of bag that gets compliments before you've even said hello. Covered in sequin floral embroidery and finished with a sleek box silhouette, this clutch brings a romantic, dressed-up feel to weddings, showers, and every RSVP on your calendar.
Fit & Features
- Sequin-embellished flower designs
- Structured box clutch silhouette
- Polished hardware trim
- Detachable chain strap
- Spacious interior
Style Number/Barcode: 07204-000061
Category Name: Vacation Looks
Price: $28.90
Availability: Out of Stock
Product Badge:- Ships Free
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Studded Style Open Back Top
Your outfit just got sharper. This crop top brings a plunge cowl halter neckline, tie straps, allover studded embellished trim, and an open back that makes everyone look back.
Fit & Features
- Slinky knit stretchy fabric
- Plunge cowl halter neckline with tie straps
- Open back
- All-over studded trim
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000690
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Cute Plans Puff Sleeve Tie-Front Top
Cute plans just found their outfit. This tie-front top pairs a flattering fitted shape with playful puff sleeves, making it an easy pick for brunch dates, rooftop drinks, and every RSVP in between. Style with the matching mini skort.
Shop Matching Bottoms: Cute Plans Wrap-Front Mini Skort
Fit & Features
- Linen-blend cotton woven fabric, sewn-in knit lining
- Short puff sleeves
- Deep V-neckline
- Dual tie-front design
- Fitted mid-length hem
Style Number/Barcode: 06003-000366
Category Name: Vacation Looks
Price: $13.97 $32.90
On Sale: Yes
Availability: In Stock
Available Color: RED
Available Size: XS, S, M, L
Product Badge:- Sale
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Polished Trouble Chiffon Halter Top
This top does all the flirting for you. The chiffon halter top features a draped sleeveless fit with an open back and tie details that instantly dress up every last-minute dinner invite.
Fit & Features
- Sheer chiffon fabric
- Sleeveless high halter neckline with tie strap
- Open back with tie strap
- Relaxed fit
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06003-000359
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: IVORY
Available Size: L
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Sweet Spot Polka Dot Capri Leggings
The vintage-inspired pair your closet has been waiting for. These polka dot capri leggings are finished with delicate lace trim for an effortlessly playful look that feels just as cute with kitten heels as it does with an oversized knit.
Fit & Features
- Polka dot print, knit fabric with stretch
- Lace trim mid-rise waist
- Form-hugging fit
- Capri-length silhouette
- Runs true to size
Style Number/Barcode: 06502-000123
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BLK/WHT-2
Available Size: S, M
Product Badge:- Best Seller
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Weekend Replay Off Shoulder Top
With an off-the-shoulder neckline, fitted ribbed knit, and nostalgic stripe pattern, this crop top is the perfect match for spontaneous weekend plans.
Fit & Features
- Striped pattern, rib knit fabric
- Off-the-shoulder neckline
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06002-000620
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: MULTI
Available Size: M, L
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Easy Escape Textured Stripe Halter Dress
Made for sunshine-filled plans and easy outfit decisions. This textured stripe dress features a smocked halter bodice and a softly flared skirt that creates beautiful movement with every step. Perfect for beach vacations, brunch dates, and warm-weather weekends that call for effortless style.
Fit & Features
- Texture striped knit fabric, partial knit lining
- Halter neckline with tie straps
- Open back
- Flowy silhouette with a ruffle hem
- Runs true to size
Style Number/Barcode: 05102-000753
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
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RSVP Ruffle Chiffon Maxi Dress
Dress code understood. This chiffon maxi dress brings the pretty with an eyelash-trim V-neckline, bust-tie front, and tiered, ruffled silhouette made for bridal celebrations, fancy brunches, and dressy soirees.
Fit & Features
- Chiffon fabric, short woven lining
- Eyelash lace trim V-neckline, tie front bust
- Underbust and bodice eyelash trimming
- Adjustable spaghetti straps
- Hidden back zipper and hook-eye closure
- Tiered ruffled maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-001494
Category Name: Vacation Looks
Price: $64.90
Availability: Out of Stock
Product Badge:- Ships Free
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Uptown Mood Chain Strap Shoulder Bag
Quiet luxury, but make it every day. This structured shoulder bag features a sleek chain strap and polished hardware—perfect for dressing up your daytime looks or finishing off your night-out lineup.
Fit & Features
- Half chain and faux leather shoulder strap with snap button closure
- Front strap with hardware insert
- Top zipper closure
- Spacious interior with zipper pocket
- Faux leather material
Style Number/Barcode: 07203-000155
Category Name: Vacation Looks
Price: $26.90
Availability: Out of Stock
Product Badge:- Ships Free
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Such A Flirt Polka Dot Mesh Cowl Neck Top
Okay, but this top just RSVP’d yes for you. This polka dot mesh cowl neck top drapes perfectly with a plunging halter neckline and flirty open back, making it your go-to for party plans, birthday dinners, or that last-minute invite that has you walking in like you planned it all week.
Shop Matching Bottoms: Such A Flirt Polka Dot Mesh Mini Skort
Fit & Features
- Polka dot mesh fabric, high stretch
- Sleeveless plunging cowl neckline, bar strap detail
- Halter strap with dual button closure, open back
- Draped cropped hem
- Runs true to size
Style Number/Barcode: 06001-000471
Category Name: Vacation Looks
Price: $26.90
Availability: Out of Stock
Product Badge:- Ships Free
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Weekend Vibes Fringe-Trim Halter Top
Your weekend lineup just found its new favorite top. This fringe-trim halter top hugs in all the right places with textured knit fabric and a strappy open back that’s made for sunny days, concerts, and night-out plans.
Fit & Features
- Textured knit fabric
- Sleeveless high halter neckline, tie-back spaghetti straps
- Open back, dual tie-back strappy design
- Mid-length hanky hem, fringe trim
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-000293
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale