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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Palm Escape Halter Wide Leg Jumpsuit
A tropical jumpsuit made for vacations, quick escapes, and weekend plans, soaking up the sun. The draped cowl neckline keeps it soft, the open back brings the drama, and the wide leg gives it that effortless flow.
Fit & Features
- Tropical print, knit stretchy fabric
- Plunge cowl halter neckline
- Open back
- Wide-leg fit
- Runs true to size
Style Number/Barcode: 06502-000082
Category Name: Vacation Looks
Price: $22.97 $54.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- Sale
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Vacation Muse Floral Halter Maxi Dress
This is the dress that makes every plan feel like a getaway. The plunging halter keeps it bold, while the floral appliqué brings that playful, standout detail.
Fit & Features
- Statement floral applique, stretch knit fabric
- Plunge halter neckline
- Open back design with tie
- Center back slit
- Form-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000446
Category Name: Vacation Looks
Price: $20.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spotted And Booked Polka Dot A-Line Mini Dress
Already RSVP’d and now you have the dress. This polka dot A-line mini dress hugs just right up top, then flares for that easy, flirty fit you’ll wear from dinner plans to after.
Fit & Features
- Ribbed knit fabric, high stretch
- Polka dot print
- Sleeveless V-neckline, eyelet trim, bow detail
- Adjustable thin eyelet shoulder straps
- Mini-length hem, ruffled trim
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000729
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L, XS
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Vacay Mindset Tropical Flower Heels
These floral strap heels bring a soft, elevated feel with delicate straps and statement blooms perfect for vacations, bridal celebrations, or weekend looks.
Fit & Features
- 3.5" Stiletto heel
- Square toe
- Tropical flower inset
- Strappy toe design
- Luxe fit cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-000633
Category Name: Vacation Looks
Price: $30.90
Availability: In Stock
Available Color: WHITE
Available Size: 6.5, 7, 7.5, 8, 8.5, 9
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Always Out Animal Open Back Maxi Dress
Walk in, and suddenly everyone’s paying attention. This cowl neck maxi dress drapes effortlessly with a bold print, open back, and high slit that was made for cocktail hour.
Fit & Features
- Animal print, mesh-lined stretchy fabric
- Cowl halter neckline, tie straps
- Open tie-back design
- High side slit
- Form-hugging maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000342
Category Name: Vacation Looks
Price: $21.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: RED
Available Size: XS, S, M, L
Product Badge:- Sale
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Marva Floral Lace-Up Mesh Formal Dress
Special Occasion
Sleek, sculpted, and made for a double-take moment—the Marva mesh mermaid gown is all about confident curves and effortless allure. Featuring a softly structured square neckline, delicate straps, and a lace-up back with ruched detailing, it’s designed to contour and captivate from every angle.
Fit & Features
- Floral abstract print, mesh fabric with full-length lining, moderate stretch
- Sleeveless square neckline, spaghetti straps
- Open strappy lace-up back design with tie closure
- Ruched lower back detail
- Floor-length mermaid silhouette
- Runs true to size
Where to Wear:
Weddings, garden parties, formal outdoor events, anniversaries, vacations, honeymoons, baby showers, bridal showers, fancy brunches, and birthday dinners.
Style Number/Barcode: 05002-001696
Category Name: Vacation Looks
Price: $64.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
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Fresh Bloom Floral Chiffon Mini Dress
This floral mini dress features a strapless smocked bodice with layered ruffles that give you that flirty, floaty feel from day dates to weekend plans.
Fit & Features
- Floral print, chiffon fabric, lining
- Strapless neckline
- Stretchy smocked bodice
- Layered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001036
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty Vibe Eyelet Skater Dress
Soft, flirty, and low-key unforgettable—this is the dress you reach for when the day turns into a whole moment. The eyelet skater dress hugs up top, flows out just right, and gives you that easy, pretty vibe from brunch to golden hour.
Fit & Features
- Woven eyelet fabric with lining
- Sleeveless square neckline
- Adjustable spaghetti straps
- Open tie-back design
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05101-000922
Category Name: Vacation Looks
Price: $14.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Polished But Fun Skater Mini Dress
Clean, classic… and cuing all the compliments. This striped skater mini dress brings that tailored, put-together vibe with a cinched bodice and flared skirt perfect for sunny days.
Fit & Features
- Striped pattern, linen-like woven fabric
- Square neckline, spaghetti straps
- Hidden side pockets
- Skater mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000776
Category Name: Vacation Looks
Price: $40.00 $56.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
Product Badge:- Sale
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Flirty Confidence Lace One-Shoulder Mini Dress
A little bold, a little soft—exactly the balance you were going for. This lace one-shoulder A-line mini dress hugs up top and flares at the hem, giving you that confident, caught-in-the-moment kind of vibe.
Fit & Features
- Lace fabric with knit lining, high stretch
- Sleeveless one-shoulder neckline, tank straps
- Fitted bodice, ruched detailing
- Drop waist design
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000778
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: YELLOW
Available Size: S, M, L
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Daydream Date Floral Maxi Dress
This floral maxi dress flows with every step, featuring a square neckline and tiered ruffle layers that feel light, pretty, and ready for any invite and celebration!
Fit & Features
- Delicate floral print, chiffon-lined fabric
- Square neckline, spaghetti straps
- Tie-back design
- Tiered ruffled A-line silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-001029
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dream State Flare Sleeve Crop Top
A little sheer, a little mystical, exactly your vibe. This floral butterfly top features a plunge tie front neckline and bell sleeves that create a dramatically cute look for concerts, festivals, or nights-out.
Shop The Matching Skirt: Dream State Ruffle Mini Skirt
Fit & Features
- Butterfly floral tie-dye print
- Mesh-lined fabric
- Long bell flare sleeves
- Plunge tie-front neckline
- Ultra-cropped length hem
- Runs true to size
Style Number/Barcode: 06202-000108
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: PINK
Available Size: L
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Sweet Touch Flower Earrings
Instant outfit glow-up, no effort required. These resin flower drop earrings add a soft, feminine finish that makes even your simplest look feel styled.
Fit & Features
- Sculpted floral design
- Attached hoop
- Polished resin material
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000351
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Island Nights Mesh Halter Maxi Dress
Vacay booked. This tropical mesh maxi dress brings that breezy, curve-skimming fit with a trendy ruffled slit that moves with you from beach cocktails to dinner.
Fit & Features
- Tropical print, mesh fabric, soft knit lining
- Halter V-neckline with hardware insert
- Tie straps, open back
- High front ruffled slit
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000607
Category Name: Vacation Looks
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Plans Booked Halter Slit Maxi Dress
This is the dress you slip on when you want all eyes on you! Designed with a sleek halter neckline, curve-hugging fit, and statement front slit with hardware detail, this maxi dress brings the chic drama.
Fit & Features
- Knit stretchy fabric
- Halter neckline, tie straps
- Drop waist seam
- High front slit
- Curve-hugging fit
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001180
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flowy Mood Chiffon Ruffle Poncho
Light, airy, and a little bit extra in the best way. This flowy chiffon ruffle poncho drapes effortlessly with an off-the-shoulder moment that feels both relaxed and styled for wherever the day takes you.
Fit & Features
- Chiffon fabric with lining
- Asymmetric off-the-shoulder neckline
- Ruffled sleeves
- Cropped hem
- Flowy fit
- Runs true to size
Style Number/Barcode: 06003-000477
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: BURGUNDY, YELLOW-2
Available Size: XS, S, M, L
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Meet Me Out Beaded Handle Bag
Booked the reservation just to carry this. This raffia bag features a statement beaded handle and spacious interior—perfect for brunch, strolling beach cities, and every outfit that needs a little extra.
Fit & Features
- Beaded straps
- Detachable crossbody strap
- String tie accents
- Slouchy silhouette
- Spacious interior
- Raffia material
Style Number/Barcode: 07203-000144
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: NATURAL
Available Size: NS
Product Badge:- Best Seller
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Prowlin' Tiger Mesh Mini Dress
Spotted: you owning every room you walk into. This tiger print mesh mini dress features a strapless neckline and breezy A-line fit—perfect for downtown plans, birthday dinners, and when your outfit needs to do the flirting.
Fit & Features
- Tiger print, sheer mesh fabric, lined
- Strapless neckline
- Flowy A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000962
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Retro Crush Floral Chiffon Mini Dress
Serving vintage flirt energy in this floral mini dress. It brings the vibe with a breezy A-line fit, playful cutouts, and a tie-front bust made for sunny days.
Fit & Features
- Vintage-inspired floral print
- Chiffon fabric, smooth woven lining
- V-neckline, tie-front bust, adjustable spaghetti straps
- Stretchy smocked back panel
- Side cutouts along the bodice
- A-line fit, ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000775
Category Name: Vacation Looks
Price: $35.00 $49.90
On Sale: Yes
Availability: In Stock
Available Color: LAVENDER
Available Size: S, M, L
Product Badge:- Sale
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Vacay Calling Wide Leg Jumpsuit
Booked the vibe before the trip even started. This tropical print jumpsuit flows easily with every step, perfect for sunset dinners, strolling the beach, or wherever the day takes you.
Fit & Features
- Tropical floral leaf print, knit fabric, bust lining
- Tube strapless neckline
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-000089
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Laren Metallic Halter Mermaid Formal Dress
Special Occasion
Designed to captivate from every angle, the Laren metallic knit mermaid gown brings sleek drama to the moment. A plunge halter neckline with hardware draws the eye, while an open bar back and fluid floor-length hem create a striking, sculpted finish.
Fit & Features
- Metallic knit-lined fabric with plenty of stretch
- Plunge halter neckline with statement hardware detail
- Cutout waist design, back zipper and hook-eye closure
- Open bar back for an elevated, modern reveal
- Mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Destination weddings, vacations, getaways, luxury resort celebrations, anniversary dinners, fashion-forward occasions, cocktail parties
Style Number/Barcode: 05002-000993
Category Name: Vacation Looks
Price: $19.97 $79.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Sale
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Keep It Cute Bodycon Mini Dress
This one just feels like a good idea. A ruched tank mini dress that smooths and shapes with a barely-there feel, made for last-minute plans you’re definitely saying yes to.
Fit & Features
- Smooth knit-lined stretch fabrication
- V-neckline with tank straps
- All-over ruched detailing
- Bodycon mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000704
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
Product Badge:- Sale
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RSVP Pretty Floral Chiffon Maxi Dress
If the invite says dress up, this floral chiffon dress is ready to make an entrance. Designed to flow effortlessly with a cinched waist and airy skirt that feels just right for showers, brunches, and every dressy celebration.
Fit & Features
- Floral pattern, chiffon fabric, smooth woven lining
- Halter neckline with tie straps
- Ruched bodice detail
- Back zipper and hook-eye closure
- Flowy A-line silhouette
- Handkerchief maxi hem
- Runs true to size
Style Number/Barcode: 05101-001393
Category Name: Vacation Looks
Price: $29.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Golden Hour Charms Double Layer Belly Chain
Tiny details, big impact. This double-layered belly chain stacks delicate charms for that effortless styled vibe, whether it’s peeking over denim or paired with your beach plans.
Fit & Features
- Layered metal belly chain
- Mixed charms with cross and gem accents
- Layered stacked silhouette
- Adjustable lobster clasp closure
Style Number/Barcode: 07002-000390
Category Name: Vacation Looks
Price: $19.90
Availability: In Stock
Available Color: GOLD
Available Size: NS