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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Wild Card Chiffon Halter Mini Dress
This chiffon halter dress combines a bold mixed animal print, open back, and flowing hanky hem for a look that feels equal parts daring and unforgettable. Style with sandals for vacations, date nights, or parties.
Fit & Features
- Animal print chiffon fabric, lined
- Halter neckline, hardware insert, tie straps
- Open back design
- Flowy A-line silhouette
- Hanky mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001177
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Set The Mood Abstract Print Halter Maxi Dress
Some dresses complete the outfit. This one sets the entire mood. This abstract print halter maxi dress combines a dramatic plunging cowl neckline, sculpting ruching, and a fluid front sash for a look that feels both gallery opening and late-night dinner reservation.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Abstract print
- Sleeveless plunging cowl neckline, bar strap detail
- Tie-back halter straps, open back, lower back spaghetti straps
- Front sash accent, ruched detailing
- Maxi-length hem, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-001173
Category Name: Vacation Looks
Price: $56.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
Product Badge:- New Arrival
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Shay Tropical Printed Bead Mini Dress
Special Occasion
Made for the nights when blending in simply isn't on the itinerary, the Shay mini dress brings bold glamour to every RSVP. This beaded mesh dress features a sculpted strapless silhouette, intricate tropical-inspired print, and a twisted sweetheart neckline that catches attention from every angle.
Fit & Features
- Printed tropical design, beaded embellishments, mesh-lined fabric
- Strapless sweetheart neckline,
- Bodycon mini-length silhouette
- Runs true to size
Where to Wear:
Bachelorettes, birthday dinners, date nights, cocktail parties, fashion-forward events, vacations, honeymoons, resort getaways
Style Number/Barcode: 05001-000783
Category Name: Vacation Looks
Price: $89.90
Availability: In Stock
Available Color: BLACK
Available Size: XXS, XS, S, M, L
Product Badge:- Ships Free
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Island Intentions Satin Mini Dress
The dress to pack in your suitcase. Designed with a tropical-inspired print, beaded straps, and a lace-up open back, this satin mini dress was made for oceanfront dinners and resort cocktails.
Fit & Features
- Silky satin woven fabric
- Subtle tropical print
- Square neckline
- Beaded spaghetti straps
- Lace-up open back
- Curve-hugging, mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000596
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Destination Glam Abstract Print Halter Top
Booked, busy, and dressed like the destination. This abstract print halter top features a plunging neckline and ruched fit that hugs in all the right places for rooftop dinners, resort nights, and every plan in between. Pair with the matching maxi skirt.
Shop Matching Bottoms: Destination Glam Abstract Print Maxi Skirt
Fit & Features
- Sleek knit fabric, high stretch
- Abstract print
- Sleeveless deep V-neckline
- Tie-back halter straps, partially open back
- Ruched bodice
- Mid-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000687
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Garden Glow Flower Statement Earrings
These dimensional acrylic flower earrings feature vibrant petals and a rhinestone-embellished center, making them the perfect finishing touch for vacations, brunch, and every outfit that could use a playful pop.
Fit & Features
- Dimensional flower
- Mini rhinestone embellished center
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000384
Category Name: Vacation Looks
Price: $13.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: NS
Product Badge:- New Arrival
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Sunny Side Up Aviator Sunglasses
These colored aviator sunglasses bring a retro-inspired feel with an effortless cool factor that works from beach days to city strolls.
Fit & Features
- Square-shaped aviator silhouette
- Rubber nose supports
- Tinted lenses
- 100% UV protection
- Lightweight frame
Style Number/Barcode: 07008-000160
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: YELLOW
Available Size: NS
Product Badge:- New Arrival
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Pretty Please Flower Earrings
Cute from every angle and impossible to overlook. These flower earrings feature delicate petal studs with dangling gem charms that add the prettiest finishing touch to looks for brunch, parties, or vacations.
Fit & Features
- Flower designs, mini rhinestone embellished center
- Dainty chain fringe
- Teardrop rhinestone charm
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000479
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: PINK
Available Size: NS
Product Badge:- New Arrival
- Flower designs, mini rhinestone embellished center
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Tropical Flair Four-Pack Hair Clips Set
Your messy bun just booked a one-way ticket somewhere tropical. These tropical flower clips add the cutest little finishing touch to beach days, dinner plans, and every photo you almost didn’t post.
Fit & Features
- Four-pack hair clips set
- Tropical flowers
- Clip closure
Style Number/Barcode: 07006-000134
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: PINK
Available Size: NS
Product Badge:- New Arrival
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Weekend Worthy Tropical Floral Tube Top
One top, endless outfit screenshots. This tropical floral tube top combines a sleek strapless silhouette with adjustable drawstring details for a look that's effortlessly on-trend.
Fit & Features
- Knit fabric, high stretch
- Large tropical floral print
- Strapless straight-across neckline
- Ruched side seams, adjustable drawstrings
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000619
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Packed And Polished Hair Claw Clip
Your updo just booked a vacation. This clear embellished tropical flower hair claw clip adds a playful finishing touch to messy buns, sleek twists, and every warm-weather outfit in between.
Fit & Features
- Hair claw clip silhouette
- Tropical flower design
- Embellished detailing
- Clip closure
Style Number/Barcode: 07006-000150
Category Name: Vacation Looks
Price: $8.90
Availability: In Stock
Available Color: BLUE
Available Size: NS
Product Badge:- New Arrival
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Desert Disco Beaded Bra Top
Made for head-turning stares. With intricate beadwork, cascading draped strands, and an open back silhouette, this statement bra top brings a festival-luxe feel that looks straight off a designer runway.
Fit & Features
- Beaded embellishments, knit fabric
- Halter neckline, tie straps
- Open back with tie
- Cascading beaded front drape
- Bra top silhouette
- Runs true to size
Style Number/Barcode: 06001-000623
Category Name: Vacation Looks
Price: $49.90
Availability: Out of Stock
Product Badge:- Ships Free
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Destination Glam Abstract Print Maxi Skirt
Booked, busy, and dressed like the destination. This abstract print maxi skirt features a ruched waist and high-cut side slit that creates a flowy fit for rooftop dinners, resort nights, and every plan in between. Pair with the matching halter top.
Shop Matching Top: Destination Glam Abstract Print Halter Top
Fit & Features
- Sleek knit fabric, high stretch
- Abstract print
- High-rise waist, ruched detailing
- High-cut side slit
- Maxi-length hem
- Flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 06501-000180
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- Part of a Set