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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Rhinestone Short Wedge Heels
Do glam the comfortable way! These super cute silver wedges feature a rhinestone-embellished, single strap upper, an ankle strap with buckle, and a short wedge heel.
Style Number/Barcode: 07406-0028
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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The Next Level Wedge Heels
Elevate your look to the next level with these chic black wedges! They feature a closed back, an adjustable ankle strap, an open toe with single strap design, a wide platform and wedge heel. They are composed of a faux nubuck material and a faux leather insole lining.
Style Number/Barcode: 07406-0000
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Upscale Filigree Wedge Heels
Take it up a notch in these designer inspired wedge heels! They feature a gold filigree design against a black background, an open toe, single strap design, and an adjustable ankle strap.
Style Number/Barcode: 07406-0002
Category Name: Vacation Looks
Price: $18.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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So Gladiator We Met Sandals
Let these tan gladiator sandals become your new bffs. They feature a faux leather, multi strap design, a back zipper and a slight wedge heel. Sandals are composed of a faux leather material.
Style Number/Barcode: 07404-0486
Category Name: Vacation Looks
Price: $4.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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My Level Block Heels
Everyone will want to get on your level of style with these chic block heels! They feature an open toe, a caged design with an adjustable ankle strap, a side zipper closure, an open heel, and a low block heel. The tan hued shoes are composed of a smooth faux nubuck material with a faux leather insole.
Style Number/Barcode: 07404-0481
Category Name: Vacation Looks
Price: $21.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Rhinestone Cross Strap Sandals
Add some bling to your casual sandal game with this silver pair of rhinestone sandals. They feature an open toe, cross strap design, silver bling, and a cork-like sole.
Style Number/Barcode: 07404-0521
Category Name: Vacation Looks
Price: $11.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Gemstone T Strap Sandals
Shine like the rare gem you are with these dazzling sandals! They feature an open back, a slip on ankle strap, a gemstone embellished gold T strap and a flat faux leather foot bed.
Style Number/Barcode: 07404-0497
Category Name: Vacation Looks
Price: $12.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Essential Double Band Slides
Slip on these casually cute slides to complete your look! They feature an easy slip on design, wide black straps and a flat faux leather foot bed.
Style Number/Barcode: 07404-0472
Category Name: Vacation Looks
Price: $12.97 $17.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sassy H Band Slides
Serve up sass in these stylish slides! They feature a combination black with tan hue, a faux leather H shaped band and an easy slip on design.
Style Number/Barcode: 07404-0462
Category Name: Vacation Looks
Price: $12.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Strappy Sleek Snake Sandals
Keep it sleek and chic in these must have sandals! They feature a flat design, natural hued snake print straps and an adjustable buckle. Sandals are composed of a faux leather material.
Style Number/Barcode: 07404-0029
Category Name: Vacation Looks
Price: $12.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glitz In Rhinestones Chrome Sandals
Keep it luxe in these sparking silver chrome sandals! They feature a wrap around rhinestone embellished spiral strap, an open back, an open toe with two rhinestone embellished straps and a low heel. Sandals are composed of a metallic faux leather material.
Style Number/Barcode: 07404-0012
Category Name: Vacation Looks
Price: $12.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Luxe Pearl Chrome Sandals
Shine like the rare beauty you are in these luxe sandals! They feature a silver hue, a wrap around pearl embellished spiral strap, an open back, an open toe with a multi strap design and a low heel. Sandals are composed of a metallic faux leather material.
Style Number/Barcode: 07404-0011
Category Name: Vacation Looks
Price: $14.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Single Strap Flat Platform Sandal
Basic can be trendy too! These black sandals feature a thick flat sole, a single strap upper and an ankle strap with buckle.
Style Number/Barcode: 07404-0008
Category Name: Vacation Looks
Price: $12.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Chic Style Long Sleeve Ribbed Knit Midi Dress
The perfect blend of casual and chic, this ribbed knit midi dress features a V-neckline, long fitted sleeves, and a form-hugging silhouette. Style with hoop earrings and sneakers for a cute everyday look.
Fit & Features
- Hacci ribbed knit fabric, plenty of stretch
- V-neckline
- Long fitted sleeves
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5920
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Get Low Strap Block Heels
Keep it simple and chic with these low heel beauties! They feature a silver hue, an closed back, an adjustable ankle strap, an open toe with single strap design. Heels are composed of a faux metallic faux patent leather material and faux leather insole lining.
Style Number/Barcode: 07401-1965
Category Name: Vacation Looks
Price: $22.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chrome A Little Closer Block Heels
Don't be afraid to come a little closer in these must have heels! They feature an open toe, single strap design and an ankle strap with buckle. Both with an iridescent sheen. They also feature a chrome block heel.
Style Number/Barcode: 07401-0143
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Buckle Up Block Heels
Buckle up in these chic heels to complete your look! These black heels feature an open back, a wide adjustable ankle strap, an open toe with single strap design and a stacked block heel. They are composed of a faux leather material.
Style Number/Barcode: 07401-0037
Category Name: Vacation Looks
Price: $23.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Palm Paradise Wrap Cover Up
Transport yourself to an island paradise with this cabana worthy cover up! This swim wrap features a palm leaf design, an asymmetrical hem, and tassels. Wrap is composed of a sheer, soft woven fabric.
Style Number/Barcode: 07305-0973
Category Name: Vacation Looks
Price: $1.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Mesh Tassel Wrap
Layer on this cute black cover up for a chic touch to your swim look! It is composed of a sheer, stretchy mesh fabric with a fun tassel trim all around.Model is 5'7" with a 34" bust, 24" waist and 36" hips.
Style Number/Barcode: 07305-0001
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Chic Floppy Hat
This season go for wild chic! This tan floppy heat features a wide brim with a trendy snake print bow.
Style Number/Barcode: 07302-1301
Category Name: Vacation Looks
Price: $3.73 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Classically Chic Floppy Derby Hat
Create a classically chic look with this black floppy derby hat! It features a wide brim design with a black trim and black bow.
Style Number/Barcode: 07302-1277
Category Name: Vacation Looks
Price: $16.90
Availability: Out of Stock
Product Badge:- Ships Free
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Socialite Large Floppy Hat
The race is on! Cheer on from the stands, or complete your garden party look with this sophisticated large floppy hat! It features a white stripe around the brim, and a band with a tie detail at the back. Hat is composed of a woven straw material.
Style Number/Barcode: 07302-1265
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lucky Charm Script Cap
Get lucky in this festive green cap! It features a flat brim, adjustable back, and the words "lucky charm" embroidered on the front.
Style Number/Barcode: 07302-1260
Category Name: Vacation Looks
Price: $3.23 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Spotted And Stylish Leopard Cap
Get spotted in this fierce hat! It features an all over leopard print, a baseball cap design and and adjustable strap with velcro detail.
Style Number/Barcode: 07302-1264
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free