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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Studded Shield Sunglasses
You'll be stuntin' and shinin' all day long in these statement sunglasses! They feature a flat top, a large square shield design, and gradient black lenses with small stud accents.
Style Number/Barcode: 07008-0531
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sassy And Stylish Sunglasses
Look totally sassy and like a total babe in these stylish sunnies! They feature a mini octagon shaped design with lenses and a frame.
Style Number/Barcode: 07008-0505
Category Name: Vacation Looks
Price: $2.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Edgy Narrow Cat Eye Sunglasses
Add some edge to your look with these black narrow cat eye sunnies! They feature dark lenses with a trendy cat eye frame.
Style Number/Barcode: 07008-0466
Category Name: Vacation Looks
Price: $2.23 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Rimless Heart Sunglasses
Experience more fun when you see the world through these sunglasses! They feature heart-shaped lenses with a rimless design and includes nose pads for a comfortable wear.
Style Number/Barcode: 07008-0461
Category Name: Vacation Looks
Price: $2.73 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Radiant Rhinestone Bobby Pin Set
Give your tresses some major highlight with a gorgeous bobby pin! This pack includes 6 hued rhinestone embellished bobby pins to give your hairstyles a dazzling look!
Style Number/Barcode: 07006-0905
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Neon Scrunchie Multi Pack
Add some fun color to your tresses with this neon scrunchie multi pack! It features five individual scrunchies in black, orange, yellow, pink, and white. Hair accessories are composed of a knit fabric.
Style Number/Barcode: 07006-0912
Category Name: Vacation Looks
Price: $2.97 $6.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Take Your Pick Scrunchie Multi Pack
Serve up a sassy updo for your tresses with a classic scrunchie! This variety pack includes five scrunchies in a variety of colors featuring velvet, eyelet and knit fabrics.
Style Number/Barcode: 07006-0894
Category Name: Vacation Looks
Price: $3.23 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Retro Vibes Scarf Scrunchie
Play up your pretty tresses and get those retro vibes with this adorable scarf scrunchie! It features a classic scrunchie design with a long scarf attached for a cute wrap look. The accessory features a brown hued bunched fabric with an elastic that flows out and is detailed with a white polka dot print .
Style Number/Barcode: 07006-0893
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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O-Ring Headband Pack
These adorable headbands will help keep your pretty tresses in place! The pack features two ribbed knit headbands in mauve and tan with gold metal O-ring details.
Style Number/Barcode: 07006-0892
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek Ponytail Cuff
Hold back your pretty tresses with this sleek gold ponytail cuff! The cuff is composed of a smooth gold metal and is attached to a black elastic band to keep your pretty ponytail in place.
Style Number/Barcode: 07006-0899
Category Name: Vacation Looks
Price: $2.97 $6.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stripes And Spots Scrunchie Scarf Set
Treat your tresses to a cute updo for an effortlessly chic look! This set includes two hair ties with a classic scrunchie design paired with a faux scarf tie for the perfect wrap appearance. One hair tie features a black and white striped design while the other features a fierce leopard print.
Style Number/Barcode: 07006-0890
Category Name: Vacation Looks
Price: $3.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Heart Hair Clip
Accessorize your pretty hair with this gold metal hair clip! It features a heart shaped design with a barrette closure.
Style Number/Barcode: 07006-0031
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic In Pearls Bobby Pin Set
Get a chic look in this pretty pearl bobby pin set! The multi-pack features four gold metal bobby pins adorned with varying sized pearl details.
Style Number/Barcode: 07006-0026
Category Name: Vacation Looks
Price: $2.73 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Treat Yourself Mid-Rise Pleated Denim Mini Skirt
Treat yourself to something new! This mid-rise pleated denim mini skirt is just the trend piece your weekly lineup needs for a cute refresh this season.
Fit & Features
- Non-stretch denim fabric
- Mid-rise dual belted waist
- Back zipper and hook-eye closure
- Pleated silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06601-0232
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Elegant In Pearls Bobby Pin Set
Add a finishing touch to your elegant look with this statement pearl bobby pin set! The multi-pack features three gold metal bobby pins, each showcasing an intricate design of pearl details.
Style Number/Barcode: 07006-0025
Category Name: Vacation Looks
Price: $3.23 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pleated Knot Headband
Slip this pleated headband on for a super cute look. It features a top knot design.Style Number/Barcode: 07006-0017
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Gorgeous In Pearls Bobby Pin Set
Dress up your hair and get a gorgeous look with this pearl bobby pin set! The multi-pack features four pins, each with a single row of rhinestones adorned on the gold metal pin.
Style Number/Barcode: 07006-0024
Category Name: Vacation Looks
Price: $2.73 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Geometric Goddess Hair Pin Pack
Give your tresses a gorgeous touch with a pretty hair pin! This variety pack includes four gold hued geometric shaped pins that easily slide on to create your favorite hairstyles!
Style Number/Barcode: 07006-0019
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sassy Snap Clips
You love a bold statement! Keep is sassy and sleek with a hair clip! Easily snap on one of these gold hued hair clips to create the perfect hairstyle! Pack includes 6 hair clips.
Style Number/Barcode: 07006-0020
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rainbow Rhinestone Hair Pins
Brighten your look with a pop of color! These sparkling hair pins are adorned with rainbow hued rhinestones. Pack includes 5 hair pins.
Style Number/Barcode: 07006-0015
Category Name: Vacation Looks
Price: $4.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty In Pearls Hair Pins
Look oh so pretty in pearls with this set of three gold hair pins! It features two bobby pin style pins and one snap clip, each adorned with varying sized pearls.
Style Number/Barcode: 07006-0006
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Bohemian Variety Ring Pack
Adorn your look with these statement rings! This pack includes ten silver rings with bohemian inspired designs to easily stack or wear alone.
Style Number/Barcode: 07004-0990
Category Name: Vacation Looks
Price: $2.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dainty Metal Leaf Hair Pins
Get naturally inspired with these precious hair pins! They feature a gold hue and dainty leaf design. Pack includes two hair pins.
Style Number/Barcode: 07006-0001
Category Name: Vacation Looks
Price: $2.97 $6.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Moon & Stars Dainty Rings Pack
Wear the moon and stars you love with this dainty rings pack! This set of 5 features gold rings in various styles, from a gemstone, simple and textured bands, geometric shapes, to moon and star charms.
Style Number/Barcode: 07004-0984
Category Name: Vacation Looks
Price: $9.90
Availability: Out of Stock
Product Badge:- Ships Free