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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Hot Tropics Side Slit Skirt
Keep the vacay vibes top of mind in this vibrant floral maxi! Skirt features an elasticized waist with a back zip, a slight A-line silhouette, and two high slits at either side. Skirt is made from a woven poly material with minimal stretch. Don't forget to pair it with the matching off-the-shoulder crop!Style Number/Barcode: 06301-0023
Category Name: Vacation Looks
Price: $4.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sleek Vibes Mini Sunglasses
Get major sleek vibes with these mini sunnies! They feature a round diamond shape with a thin metal frame and colored lenses.
Style Number/Barcode: 07008-0643
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rhinestone Five Pack Ring Set
Bring the shine with these sparkling rings! This pack features 5 bands adorned with mini rhinestones to compliment every look! Pack includes 5 rings that can worn together or separately.
Style Number/Barcode: 07004-0012
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Go With Flow Palazzo Pants
Bright white and easy breezy, these palazzo pants are the ultimate in summer chic. Pants have a high rise, an elasticized back waist, a side zip, and ultra-wide legs. Pair them with the matching crop top and turn up the heat! Pants are fully lined and made from a soft, lightweight woven material with little to no stretch.Style Number/Barcode: 06302-0040
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Take The Plunge Floral Maxi Dress
Add a hint of island-inspired chic to your wardrobe with this gauzy sleeveless maxi dress. Dress features a deep V at front and back, a shirred banded waist, and an all-over floral print. Dress is composed of a rayon fabric and has plenty of stretch in the waist and moderate stretch throughout the rest.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-4050
Category Name: Vacation Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Must-Have Tie Back A-Line Mini Dress
A must-have tie back A-line mini dress for casual nights out! Featuring chic cap sleeves, a square neckline, a sultry open back with tie closure, and a flattering A-line silhouette with a mini-length hem, this dress will elevate your style game. Complete the look in faux suede heels and a purse!
Fit & Features
- Slinky knit fabric lined with stretchy knit
- Open tie-back design
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5681
Category Name: Vacation Looks
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Love For You Mini Dress
Showcase your love for a cute pattern with this absolutely adorable printed mini! The dress features a sleeveless bodice, ruffle detail shoulder straps, a square neck and back, a hidden back zipper and hook and eye closure, a high waist seam, and side ruched detailing with a tie at the hem. The dress is composed of a lined lightweight linen fabric.
Style Number/Barcode: 05102-0285
Category Name: Vacation Looks
Price: $9.97 $47.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Denim Darling Button Midi Dress
It's all about the details with this dynamite denim midi! Dress features tank-style straps, a square neckline, vertical seam detail, a button front, belt loops and a detachable tie-front belt, pockets at either hip, and a slim, straight skirt. Dress is made from a mid-weight cotton blend with a hint of stretch.
Style Number/Barcode: 05102-0247
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Simply Stylish Sarong Cover Up
Layer on this stylish black cover up for an instantly chic beach look! The long sarong features a top tie with tassel detailing and a high side slit.Model is 5'9" with 32" bust, 24" waist and 34.5" hips.
Style Number/Barcode: 07305-0006
Category Name: Vacation Looks
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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She's A Go Getter Block Heels
Go get em in style! These short heels feature a single strap, an open toe, and an adjustable ankle strap with a pin buckle closure. These heels are lined with a faux leather material, and the heel is composed of a cork style material. Sizes run large. Fit model recommends purchasing a half size down.Style Number/Barcode: 07401-0236
Category Name: Vacation Looks
Price: $9.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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On That Wedge Heel
We love a wedge heel girl! Add this pair to your favorite summer dresses this season! The taupe wedges features a closed back, an adjustable ankle strap, an open toe with single strap design and a wedge heel. Made of a matte faux leather fabric.Style Number/Barcode: 07406-0006
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Walk Into Simplicity Sandals
A simple pair of sandals are essential to your closet! Featuring a band over the toes, a sling back style band around the ankle with an adjustable ankle strap with a pin buckle closure. The sandals are composed of a faux leather material.
Style Number/Barcode: 07404-0083
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rhinestone Knot Variety Ring Pack
Tie the knot with rhinestones! This ring pack includes a variety of 6 rings that feature a twisted knot design, chain link and mini rhinestones.
Style Number/Barcode: 07004-0013
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Sea Shell Bolo Bracelet
Get those beachy vibes going with this mermaid-approved bracelet! It features a single row of sea shell charms and a bolo tie to easily adjust.
Style Number/Barcode: 07003-2390
Category Name: Vacation Looks
Price: $2.97 $6.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sparkle And Rhine Anklet Set
Sparkle and shine with this rhinestone anklet set! The pack features two anklets with two rows of rhinestones with gold hued chains with adjustable lobster clasp closures.
Style Number/Barcode: 07003-2341
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Set Of Three Charm Chains
Layer on the charm with this set of three gold necklaces. They are of varying lengths and include ball, rhinestone, and coin charms. They close with lobster clasps.
Style Number/Barcode: 07002-5208
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Two Strap Sandals
Bite back in these fierce sandals! The sandals feature a double buckle strap design with metal hardware, a cork style footbed, an all over snake print and an easy slip on design.
Style Number/Barcode: 07404-0092
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Vacay Approved Shell Choker
This adorable shell choker is totally vacay approved! The necklace features a row of seashells woven together and includes a gold adjustable chain and lobster clasp closure.
Style Number/Barcode: 07002-0042
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Go With The Flow Tie Front Top
Go with the flow of this pretty tie front top! It features short flowy kimono style sleeves paired with a tie front and a cropped hem. The top is composed of a woven fabric with no stretch and offers a relaxed and comfortable fit.Style Number/Barcode: 06204-0077
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Always Flattering Crepe A-Line Mini Dress
This crepe cowl neck mini dress flaunts an A-line silhouette with a slit accent and spaghetti straps for a truly stylish look. Feel confident and look amazing in this fashionable, yet comfortable, mini dress that will become your go-to for any occasion! Complete the look in statement stiletto heels and a cropped jacket for dressy to semi-formal occasions!
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- A-line silhouette, slit accent
- Mini-length hem
- Crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2797
Category Name: Vacation Looks
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flaunt It Floral Crop Top
Flaunt your sweet sense of style in this charming top! It features a sweetheart bust with a tie front accent, a smocked back and an all over floral print. Top is composed of a lightweight woven fabric that offers a relaxed fit with slight stretch. Be sure to pick up the matching skirt.
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06003-0270
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Charming Crochet Crop Top
Create a charming, sweet look in this adorable crochet crop! The top features three quarter length sleeves with elastic cuffs, a square neck and back, a partially sheer crochet front with a lattice accent with tassel details, a stretchy smocked back, and a cropped hem. The top is composed of a lightweight, airy woven fabric.Style Number/Barcode: 06003-0286
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Island Time Floral Top
A graphic black and white floral set against a bold yellow background makes this crop especially eye catching. Top features crisscross adjustable spaghetti straps and an open tie back. Be sure and grab the matching maxi skirt to channel the perfect island vibe! Top is unlined and made from a lightweight woven material with little to no stretch.Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06003-0220
Category Name: Vacation Looks
Price: $8.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Off The Chain Belt
Stay trendy and hip in this must have belt! It features a gold hue, a single row chain link design and a lobster clasp closure.Style Number/Barcode: 07301-0008
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free