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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Swing My Way Denim Shorts
Sure looks good to us! Perfect for teaming with tees, cropped tops, and your fave sneakers or platforms, these cutoffs will see you through summer. Shorts feature distressed detail, a roll-cuff hem, zip fly with button closure, and a medium rise. Shorts are made from cotton and offer just a hint of stretch
Style Number/Barcode: 06603-0022
Category Name: Vacation Looks
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Feels Maxi Dress
Get all those floral feels with this beautiful printed maxi dress! It features a sleeveless bodice, spaghetti straps that cross in the back, a square neckline, a high side slit, and a long, fitted maxi length. The black floral printed dress is composed of a soft knit fabric that offers plenty of form hugging stretch.
Style Number/Barcode: 05102-3749
Category Name: Vacation Looks
Price: $13.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pixie Mid Rise Denim Shorts
Oasis by Eunina
When it comes to summer staples, look no further than these perennially cool cutoffs! Shorts feature a low rise, exaggerated frayed hem, distressed detailing throughout, zip fly, and button closure. Shorts are made from a classic cotton blend with a hint of stretch.
Style Number/Barcode: 06603-0781
Category Name: Vacation Looks
Price: $11.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Beauty In Crochet Skirt
Hey beauty, stun in this effortlessly pretty crochet skirt on your next vacay! It features a high rise elastic banded waist, a tie front, O-ring accents down the side and along the bottom, and long fringe hem details. The skirt is composed of a sheer crochet fabric that offers moderate stretch and a form hugging style.Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06501-0042
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Babygirl Striped Romper
Get girly with this adorable spaghetti strap stripe tiered pink romper! Featuring adjustable spaghetti straps that cross in the back , a V neckline, a hidden zipper in the back and tiered ruffles in the front and a ruffle style hem. It also includes a tie front belt to tie together the whole look! This romper is composed of a woven material with minimal stretch.Style Number/Barcode: 06303-0026
Category Name: Vacation Looks
Price: $4.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cozy Staple Faux Fur Ankle Booties
Fit & Features
- Flat sole
- Ankle-fit
- Almond toe
- Faux suede exterior
- Faux fur lined insole
- Runs true to size
Style Number/Barcode: 07408-0114
Category Name: Vacation Looks
Price: $28.90
Availability: Out of Stock
Product Badge:- Ships Free
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Don't Waist My Tie Mini Dress
Equal parts beachy and club-ready! Dress features a single-shoulder bodice with side cutout and waist tie and a fitted skirt. Dress slips on and is made from a soft, lightweight knit material with moderate stretch.Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05103-0115
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sally Floral Chiffon Formal Dress
Special OccasionFloaty and feminine, our diaphanous Sally dress is perfect for warm-weather special occasions. She features adjustable spaghetti straps, a V neck and back, criss cross ties at waist, zipper closure, and a gently pleated, semi-lined modified A-line skirt. Chiffon-like fabric is semi sheer from mid-thigh to hem and offers little to no stretch.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-0004
Category Name: Vacation Looks
Price: $29.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Serena Strapless Wrap Gown
Special OccasionChannel a Greek goddess in Serena, an equal parts sunny and sophisticated column gown. She features a strapless bodice, wrap-style detailing, draping at waist, a front slit, and a back zip. Serena is made from a crepe-style fabric with limited stretch and is slimly fitted through the bust, waist, and hips. She is fully lined with a smooth knit fabric that provides additional coverage for her slim fit.
Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-6678
Category Name: Vacation Looks
Price: $29.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bold And Bright Slides
Go bold and bright in these of-the-moment slides. Sandals feature a small platform, a fabric upper, and all-over embossing. Sandals are made from a plastic material.
Style Number/Barcode: 07404-0053
Category Name: Vacation Looks
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lush Life High-Low Top
Bring the heat when you don this vibrant orange high-low top. Top features a lush tropical print, deep V neckline, three-button closure at banded waist, butterfly sleeves, and open front. Top is semi-sheer and made from an ultra lightweight woven material with little to no stretch.Model is 5'8" with a 32" bust, 23" waist, and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-0025
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Knot The One Cami
Billowy and bomb, cami is of-the-moment yet understated. Top features a V neckline, adjustable spaghetti straps, cutout detail and a tie front at the waist. Top is made from a soft woven material with little to no stretch.Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06003-0173
Category Name: Vacation Looks
Price: $5.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Coming Up Roses Mini Dress
Begin to bloom the moment you step into this eye-catching floral-print mini! Dress has a deep V neckline, spaghetti straps, banded waist, cutout at back and of-the-moment lace detail with zip closure. Dress is made from a soft, moderately stretchy material.
Style Number/Barcode: 05101-0000
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Boho Beauty Tie Front Top
You'll be a stunning boho beauty in this lightweight tie front top! It features three quarter length puff sleeves with ruffled elastic cuffs, a deep V neckline created by a tie front closure, a partially stretchy smocked back, and a cropped hem. The top is composed of a textured woven fabric, perfect for those nice sunny days!Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06003-0215
Category Name: Vacation Looks
Price: $8.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Before Eyelet Go Tie-Front Top
Take your summer crop up a notch in bright white with standout details. Top features adjustable spaghetti straps, a tie front, side zipper, and a darted bodice. Top is made from a soft, ultra lightweight woven material perfect for warm weather. Be sure and grab the matching skirt!Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06003-0169
Category Name: Vacation Looks
Price: $7.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wrap me in Lace Dress
My oh my! This linen ruffle dress is too adorable! Featuring A square neckline, lace pattern, and stretchy sleeveless straps, Adorned with floral details covering the bodice, and a wrap that ties at the hip. This mini dress has a ruffle effect at the hem with a lace pattern detail. In the back this dress has a cut out and a cute bow that ties at the top, lastly there is a hidden zipper found near the lower back area. Composed of a detailed linen material with minimal stretch.
Style Number/Barcode: 05101-0111
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Getaway Today Crop Top
It's all about the vacay vibes in this sultry striped mustard crop. Top features adjustable spaghetti straps, a V neckline, twist wrap detail at front, and tie straps at back. Top is made from a midweight, linen-like material with little to no stretch. Be sure and check out the matching skirt to round out your look!Model is 5'6.5" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06003-0168
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweetly Tied Skater Dress
Sweeten up your look with this adorable red skater dress! It features a sleeveless bodice, adjustable halter straps that lead to a button back closure with a keyhole cut out below, a back zipper and hook and eye closure, a V neckline, a cute tie front detail, and a flowy skater skirt. The dress is composed of a lightweight linen fabric with a short knit lining.
Style Number/Barcode: 05102-3826
Category Name: Vacation Looks
Price: $13.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet As Pie Skater Dress
Honey you will look sweet as pie in this cute skater dress! This piece features a V neckline, spaghetti straps, a skater style skirt, and the best part...It has pockets! This dress is comprised of a soft crepe material that offers moderate stretch.Style Number/Barcode: 05101-8838
Category Name: Vacation Looks
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Glam Slip-On Clogs
Fit & Features
- Faux fur material
- Closed round toe
- Buckle strap detail
- Slip-on design
- Flat sole
- Runs true to size
Style Number/Barcode: 07405-0190
Category Name: Vacation Looks
Price: $26.90
Availability: Out of Stock
Product Badge:- Sale
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Enchanted Garden Surplice Skater Dress
Bloom into the night with this bold skater mini! Dress features a surplice-style bodice with V neck, back zip, and adjustable spaghetti straps and a flow-y, gently pleated A-line skirt with curved hem. Dress is nearly fully lined and made from a chiffon-like material with little to natural stretch.
Style Number/Barcode: 05101-0018
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Boho Bow Peasant Crop Top
A fresh, warm-weather take on the traditional peasant blouse, this breezy crop is made for summer. Features a square neckline, gathered sleeves with elasticated ruffle trim, a decorative faux button front, side zip, and smocking detail at back. Top is made from a soft, silky fabric with moderate stretch.Model is 5'6.5" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06003-0171
Category Name: Vacation Looks
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Billow Talk Crop Top
Easy breezy and elegant, this billowy cropped blouse is made for summer nights. Top features long sleeves, off-the-shoulder styling, and gathered neck, hem, and cuffs. Top is made from a soft, lightweight woven fabric with stretch at trim.
Style Number/Barcode: 06003-0039
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Gorgeous Glow Ruffle Bodysuit
Get a gorgeous glow in this ruffle bodysuit! It features a sleeveless bodice, spaghetti straps, a ruffle neckline, a tie front detail with a keyhole cut out, and a thong bottom with snap button closures. The bodysuit is composed of a soft knit fabric that offers a form hugging fit with plenty of stretch.
Style Number/Barcode: 06001-1443
Category Name: Vacation Looks
Price: $8.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance