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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Plus Crochet In Color Dress
This cute crochet dress is perfect for a day out! It features a V neckline, adjustable spaghetti straps that create an X back, a sheer crochet waist, and a short flared skirt with a full lining.
Style Number/Barcode: 15102-0018
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Into The Florals Dress
Immerse yourself in all the floral print you can take! This flower bomb features a cowl neck, adjustable narrow straps that create an X back, and a slim fit. Dress is composed of a casual knit fabric with a lightweight feel that offers plenty of stretch. Dress is unlined.Style Number/Barcode: 05102-3105
Category Name: Vacation Looks
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Crochet Fringe Shawl
Keep it timelessly elegant with a this vintage inspired shawl! It features an intricate crochet design featuring floral inspired stitching, and a fringed hem. Shawl is composed of a lightweight crochet knit fabric.Style Number/Barcode: 07305-0009
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Angled Revo Sunglasses
Angle yourself with a better view wearing these aviator sunnies! They feature a metal frame, angled nose pads and revo lenses with 100% UV Protection.Style Number/Barcode: 07008-0053
Category Name: Vacation Looks
Price: $2.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Strappy Styles Midi Dress
Strappy and stylish, this midi dress will freshen up your wardrobe. It features a sleeveless bodice, spaghetti straps, a wrap front V neckline, an open back with bar strap details, and a mid-length, form hugging fit. The dress is composed of a crepe fabric, offering moderate stretch, and includes a knit lining.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small
Style Number/Barcode: 05103-0278
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Don't You Want Me Dress
They're gonna want you AND your dress! This tank dress features adjustable shoulder straps with a back tie closure and ruched sides. It's structured with a bodycon fit and hits at the mid-thigh. Fully lined and made of a comfy, textured jersey knit fabric for dressing up or down.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0258
Category Name: Vacation Looks
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Simple And Stunning Midi Dress
Simply stunning is what you are in this trendy knit midi dress.
Fits & Features
- Bungee Spaghetti Straps
- Square Neckline
- Curve-Hugging Fit
- Midi Length Silhouette
- Soft Brushed Knit Composition | Fully Lined
- Offers Plenty Of Stretch
Hunter & Mauve: Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Black: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0175
Category Name: Vacation Looks
Price: $10.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Chills Long Sleeve Slit Mini Dress
Look cute in this mini dress for casual chills with friends or daytime outings! The mini dress features a classic crew neckline, bell long sleeves, a flattering bodycon silhouette, and a flirty front slit along the hem on rib knit fabric. Complete the look with booties and a handbag!
Fit & Features
- Bell long sleeves
- Crew neckline
- Bodycon silhouette
- Front slit, mini-length hem
- Rib knit fabric
- Minimal stretch
- Style runs small
Style Number/Barcode: 05102-5326
Category Name: Vacation Looks
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Over You Sleeveless Midi Dress
Show us who is boss in sleek midi! This mid length dress features a crew neckline, and a sleeveless bodice. Hem is tailored to a mid calf length, and dress is composed of a ponte material that offers moderate stretch. Throw on some heels and walk the walk!
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0189
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Such A Gem Body Chain
Girl, you're such a gem, and this beyond beautiful bodychain will complete your gorgeous look! It features a chain link around the neck, linked multi-faceted iridescent gemstones and rhinestones as the center statement, and dual chains to wrap around. Includes adjustable lobster clasp closures.Style Number/Barcode: 07002-0117
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Clear To Me Mules
Two complimentary textures make these slide-style sandals a must. Made from a faux suede material, they feature a thick, contrast piped PVC strap across the toes and a stabilizing block heel. Sandals have a faux leather footbed.Style Number/Barcode: 07401-0210
Category Name: Vacation Looks
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Satin Scrunchie 5 Pack
Up your fall accessories game with this sweet set of five satin scrunchies in the best cooler-weather colors! Two scrunchies feature knotted tie detail and one scrunchie features accordion-style pleats.Style Number/Barcode: 07006-0053
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Sweetheart In Satin Mini Dress
You're such a sweetheart and always have the best style, so you'll love this trendy mini! The dress features short flowy ruffle sleeves, a sweetheart neckline with a ruched tie front, a low scoop back with a continued ruffle detail and a top tie back closure, a high waist seam, and a short mid-thigh length. The dress is composed of a smooth lightweight satin-like fabric with no stretch.Style Number/Barcode: 05101-0272
Category Name: Vacation Looks
Price: $18.97 $47.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tied To Style Mini Dress
Make sure your look is totally tied to style with this adorable mini! The dress features a sleeveless bodice, tie shoulder spaghetti straps, a partial wrap front V neckline, vertical seam detailing down the bust, a square back, a high waist seam, and a short, form hugging fit. The dress is composed of a crepe fabric that offers moderate stretch and includes a knit lining.Style Number/Barcode: 05101-0183
Category Name: Vacation Looks
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Panama Posh Woven Hat
Don't miss out on this chic, two-tone woven hat. Featuring ribbon trim and a contrast brim, this paper hat keeps you cool and protected - all while looking vacay-ready.Style Number/Barcode: 07302-0102
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Do Not Disturb Woven Hat
Tell 'em what's up in this woven hat. Featuring embroidery script on the brim, this sassy and chic piece is what you need for lazy days by the pool.
Style Number/Barcode: 07302-0100
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Muneca Script Baseball Cap
Hey, babydoll, this hat is made for you! This accessory features a baseball cap design, embroidered script reading "Muñeca," and an adjustable back with a buckle closure.Style Number/Barcode: 07302-0085
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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All That Fringe Earrings
We can never get enough fringe! These chandelier shaped earrings make a bold statement that we are in love with. With a triangular design and rows of multi length rhinestone dangling fringe. Earring have a post back closure.Style Number/Barcode: 07001-0125
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Teardrop Fringe Earrings
Add some sparkle to your style! These earrings are teardrop shaped encrusted with rhinestones and dazzling with a rhinestone fringe. Earrings have a hook closure.Style Number/Barcode: 07001-0099
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
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Miss Flirtatious Maxi Dress
Feeling flirty? We see you Miss flirtatious! This piece features a square neckline and thin straps that lead to a square back. The maxi dress has a cut out detailing under the chest area, cup lining, as well as a knot front at the hip. The high side slit shows off a little leg but not too much with the skirt style hem underneath! This gorgeous dress is composed of a ribbed soft knit material that offers moderate stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0210
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Golden Glow Mini Dress
Get your glow on girl! Radiate golden hour in this perfect mini. The dress features a sleeveless bodice, adjustable spaghetti straps, an adorable tie front V neckline, a square back, a waist front cut out, a hidden side zipper and hook and eye closure, and a flowy skirt with a ruffle hem. The dress is composed of a lightweight woven fabric with a sheer skirt lining and has no stretch.Style Number/Barcode: 05101-0262
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Appeal Mock Neck Bodycon Mini Dress
A must-have basic for the upcoming season! This dress features fitted long sleeves, a mock neck, a flattering bodycon silhouette, and a mini-length hem. It's composed of a cotton-blend knit fabric with a moderate stretch for comfort. Complete the look in strappy heels for a birthday brunch!
Fit & Features
- Fitted long sleeves
- Mock neck
- Bodycon silhouette
- Mini-length hem
- Cotton-blend knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5153
Category Name: Vacation Looks
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bloom With It Mini Dress
Get with this blooming floral mini dress! It features a sleeveless bodice, spaghetti straps that lead to a cross back, a V neckline, and a short, form hugging fit with a ruffle hem. The dress is composed of a crepe fabric that offers moderate stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0254
Category Name: Vacation Looks
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Faux Leather Cabby Hat
Get ya cabby hat here, girl! This cabby hat features allover faux leather fabric with a button top and short brim.Style Number/Barcode: 07302-0015
Category Name: Vacation Looks
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance