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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Brown Sugar Breeze Cutout Maxi Dress
This strapless maxi dress brings the kind of effortless allure that looks good from beach strolls to walks back to the hotel. The smocked fit, soft cutout detail, and flowy skirt keep it stylish with a pair of sandals.
Fit & Features
- Gauze woven fabric
- Strapless sweetheart neckline
- Stretchy smocked bodice with cutout
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000602
Category Name: Vacation Looks
Price: $56.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Blue Skies And Late Nights Mini Dress
This is the dress that makes every summer plan feel a little more exciting. Featuring a breezy bandana-inspired print, open-back halter neckline, and flirty skater silhouette, it's made for vacation dinners, sunset strolls, and saying yes to plans that weren't on the calendar.
Fit & Features
- Paisley print, chiffon fabric, woven lining
- Halter neckline, spaghetti straps
- Open back
- Stretchy smocked waist panel
- Skater mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000646
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
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Trendsetter Faux Leather Shoulder Bag
Proof that the purse can carry the outfit. This faux leather shoulder bag brings a structured shape, knotted strap detail, and trendy buckle made for brunch reservations, night-out moments, and plans that keep moving.
Fit & Features
- Washed faux leather material, smooth finish
- Rectangular-shaped silhouette
- Fold-over design, buckle strap, magnetic button closures
- Shoulder strap with knotted details
- Faux leather-lined interior, single pocket
Style Number/Barcode: 07203-000177
Category Name: Vacation Looks
Price: $27.90
Availability: In Stock
Available Color: TAN
Available Size: NS
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Francine Floral A-Line Midi Formal Dress
Special Occasion
The Francine midi dress blends a soft floral print with eyelet lace trim fabric for a look that feels both romantic and refined. The sweetheart underwire bust neckline, lace-up back design, and drop waist seam create a beautifully sculpted silhouette, while the A-line midi hem with lace trim brings effortless movement to every step.
Fit & Features
- Soft floral print, cotton-blend woven fabric with eyelet lace trim
- Smooth woven lining with lace edge trim
- Sweetheart tie-bust lace trim neckline, underwire bust
- Lace trim adjustable shoulder straps, hidden side pockets
- Flexible boning inserts in the bodice, side zipper and hook-eye closure
- Lace-up back design, drop waist seam, A-line midi-length silhouette
- Runs true to size
Where to Wear:
Outdoor weddings, bridal showers, engagements, charity luncheons, dressy brunches, garden parties, afternoon tea parties, vacations, honeymoons, milestone occasions, summer cocktail parties
Style Number/Barcode: 05001-000803
Category Name: Vacation Looks
Price: $129.90
Availability: In Stock
Available Color: WHITE, PRINT
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free
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Out All Night Faux Leather Shorts
Serving after-hours confidence with every step. These faux leather shorts bring the drama with metal grommets and a leg-lengthening fit that's made for concerts, nights out, and every photo-op in between.
Fit & Features- Faux leather fabrication, sewn-in knit lining
- Low-rise waist
- Metal grommets and belt loop accents
- Side flap pockets
- Form-hugging cheeky fit
- Front hidden zipper and hook-and-eye closures
- Runs true to size
Style Number/Barcode: 06403-000152
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Kissed In Polka Dot Mesh Mini Dress
A little playful, a little risky, and fully worth the attention. This polka dot mesh mini dress hugs in all the right places with a plunge halter neckline, open back, and layered ruffle hem that was made for stealing the scene.
Fit & Features
- Polka dot print, mesh fabric, knit lining
- Plunge halter neckline, tie straps
- Open back
- Side ruched seams, fitted bodice
- Layered ruffle mini hem
- Runs true to size
Style Number/Barcode: 05102-000709
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
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Flirty Flare Polka Dot A-Line Mini Dress
Both flirty and impossible to ignore. This polka dot mini dress hugs in all the right places before flaring into an easy A-line fit that’s made for dinner dates, rooftop plans, and drinks with the girls.
Fit & Features
- Smooth knit fabric, high stretch
- Polka dot print
- Sleeveless deep V-neckline
- Adjustable spaghetti straps
- Mini-length hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000679
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Siren Vibes Shell-Trim Halter Mini Dress
Serving siren vibes. This shell-trim halter mini dress brings a plunging cowl neckline, an open tie-back design, and a ruched bodycon fit that knows exactly how to make an entrance.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Sleeveless plunging cowl neckline, bar strap detail
- Shell embellished trim
- Tie-back halter straps, open back, lower tie-back spaghetti straps
- Ruched detailing
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-000941
Category Name: Vacation Looks
Price: $54.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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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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Checked In Lace Crop Top
Booked, packed, and already thinking about the vacation photos. This lace top pairs a plunge neckline with a flirty open front for an effortlessly styled getaway look.
Shop Matching Bottoms: Checked In Lace Shorts
Fit & Features
- Lace-lined fabric
- Plunge halter neckline, tie straps
- Open front design, beaded accents
- Flowy crop-length hem
- Runs true to size
Style Number/Barcode: 06001-000683
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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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: In Stock
Available Color: BLUE
Available Size: NS
Product Badge:- Best Seller
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Café Cutie Tie-Front Top
The top that makes a simple capris-and-top combo look instantly styled. Featuring romantic ruffle trim, a tie-front closure, and a cropped silhouette, this crop top was made for coffee dates, weekend markets, and spontaneous plans.
Fit & Features
- Smooth satin fabric
- Ruffled trim tie-front neckline
- Cap sleeves
- Fitted crop-length hem
- Runs true to size
Style Number/Barcode: 06003-000348
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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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: XS, S, M, L
Product Badge:- New Arrival
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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: XS, S, M, L
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Fresh Picked Eyelet Mini Dress
This dress deserves a weekend away and a cute photo dump. The smocked eyelet mini dress features an off-the-shoulder neckline with flirty ruffle trim and an easy fit that works from brunch plans to beach town strolls.
Fit & Features
- Eyelet woven fabric
- Ruffled, off-the-shoulder neckline
- Stretchy smocked bodycon silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001037
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Blush Rush Halter Skater Dress
Cute enough to cause a double-take. This open back skater dress brings a flirty and polished vibe with a plunging neckline, trendy side pockets, and a flattering skater silhouette perfect for pairing with heels.
Fit & Features
- Smooth ponte fabric, knit stretchy lining
- Plunge halter neckline with tie straps
- Open back, zipper and hook-eye closure
- Hidden side pockets
- Skater mini-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001030
Category Name: Vacation Looks
Price: $45.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, 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: 05101-001301
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: YELLOW
Available Size: S, M, L
Product Badge:- Back In Stock
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Pretty Plans Eyelet Mini Dress
Caught feelings for this one instantly. This eyelet dress feels light and playful, perfect for brunch dates, daytime plans, or wherever the mood takes you.
Fit & Features
- Eyelet knit fabric, smooth knit lining
- V-neckline
- Adjustable spaghetti straps
- Fitted bodice
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000471
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: WHITE
Available Size: XXS, XS, S, M, L
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Island Afterglow Knit Maxi Dress
Booked the trip and get to wear this maxi dress. This long sleeve maxi dress brings that getaway glow with its open back and side slit made for sunset dinners and cocktails.
Fit & Features
- Texture knit fabric, smooth knit lining
- Plunge V-neckline, hardware insert
- Long bell sleeves
- Cutout bodice, open back
- High side slit
- Form-hugging, maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000155
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M
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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: $44.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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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: $34.90
Availability: In Stock
Available Color: WHITE
Available Size: M, L
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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: $39.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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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: $49.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L