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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Poised And Chic Satchel
Stun and complete your look with a stylish touch! This satchel features a top zipper closure, a double-compartment, a top handle, a snake print on each side to accent the solid print. Includes a faux leather shoulder strap. Handag is composed of a faux leather material.Style Number/Barcode: 07203-0067
Category Name: Vacation Looks
Price: $13.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Paradise Gemstone Earrings
Go irridescent in these bright and bold, multifaceted gemstone earrings. Topped with post back closures for easy wear.
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0148
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Darling Ditsy Floral Maxi Skirt
You'll look oh so darling in this cute ditsy floral maxi skirt! It features a high rise waist, a stretchy and smocked top, and a flowy long length. The skirt is composed of a lightweight woven fabric. Complete your look with the matching crop top!Style Number/Barcode: 06301-0022
Category Name: Vacation Looks
Price: $4.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Botanical Beauty Midi Dress
This botanical print dress features a square ruffled neckline, elastic ruffle straps and a straight bodice. The backing of the dress has a hidden zipper and stretch smock detailing.This piece has a dark toned floral print and is mid-length with a smooth inner lining and a side slit.It is composed of a sheer chiffon-like material that offers a relaxed fit with minimal stretch. On a stroll through the park or a gals brunch date, this dress is bound to have heads turning!Model is 5'9" with a 32" bust, a 24" waist, and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0210
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Miss Midi Striped Dress
Hey there miss midi, we see you! and we are on the same page too, filling our closet with midi dresses this season. This piece features a v-neckline, attached dark neutral marbled buttons, and adjustable spaghetti straps that lead to a square back. This toned midi dress has a skinny stripe pattern and is composed of a soft knit material that offers maximum stretch.
Style Number/Barcode: 05102-3992
Category Name: Vacation Looks
Price: $8.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Rainbow Wave Maxi Dress
You love color, so embrace the rainbow! All eyes will be on you in this vibrantly chic maxi dress, which features a multi-hued stripe pattern, spaghetti straps, scoop neck, pockets at either hip, and plenty of stretch. Don't forget to pair it with the matching head wrap!
Style Number/Barcode: 05102-0244
Category Name: Vacation Looks
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Surprise Wide Leg Jumpsuit
Create a sweet charming look in this super gorge jumpsuit! It features a sleeveless bodice, plunging sweetheart neckline, tie front accent with keyhole, narrow adjustable straps and a smocked back. The bodice leads to a pair of wide leg pants with high center slit for a dramatic flare! Jumpsuit is composed of a lightweight woven fabric that offers a form hugging fit with minimal stretch.Style Number/Barcode: 06302-0044
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Be Free Butterfly Sterling Silver Stud Pack
Delicate and chic, these butterfly studs can be worn solo, doubled (or tripled) up. Three pack contains one pair each of yellow gold, rose gold, and white gold studs with rhinestone embellishment and post backing. Earrings are composed of a stunning sterling silver.
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0150
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rhinestone Playboy Anklet
Glam up your style with this trendy statement piece! The chain link anklet features three rows showcasing rhinestones and a script saying "Playboy." Anklet includes an adjustable lobster clasp closure.Style Number/Barcode: 07003-0015
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Feeling Fresh And Fab Pants
Step out this season feeling fab in these essential tie waist pants! They feature a high rise paper bag waist, a cute tie front belt, front pockets, a back zipper closure, and wide pant legs. The bottoms are composed of a sheer white linen fabric with a full knit lining. Be sure to pick the matching halter top to complete your look!Model is 5'8" with a 34" bust, 25" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06302-0584
Category Name: Vacation Looks
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ready And Ruffled Mini Dress
Take on the day in pretty ruffles! This mini dress features a sleeveless bodice, a surplice wrap V-neckline with a mini snap button closure, a smocked waist and multi tiered ruffled mini length silhouette. Dress is composed of lightweight woven fabric that offers a relaxed fit with a minimal stretch.
Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0327
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dressed To Lounge Chenille Knit Catsuit
Get dressed to lounge in this chenille knit catsuit for a night in! The catsuit features a sleeveless square neckline, spaghetti straps, a flirty low scoop back, a form-hugging fit, and a skinny-leg design on ultra-soft and cozy chenille knit fabric. Complete the look in a cozy lounge sweater and slippers!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Low scoop back
- Form-hugging fit
- Skinny-leg design
- Ultra-soft chenille knit fabric
- Runs true to size
Style Number/Barcode: 07103-0948
Category Name: Vacation Looks
Price: $10.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Goody Two Shoes Rhinestone Slides
No socks needed! These rhinestone-encrusted slides feature a wide, translucent PVC band and a soft, textured rubber sole. Just slip on and go!Style Number/Barcode: 07404-0094
Category Name: Vacation Looks
Price: $12.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Coconut Kisses Wide Leg Jumpsuit
Wow - tropical babe in the house! This cute jumpsuit has a V-shaped neckline and flirty back bow detail with an elasticized waist.Style Number/Barcode: 06302-0063
Category Name: Vacation Looks
Price: $4.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wandering Woman Romper
You're a traveling lady. This ruffle romper features a surplice front and flouncy sleeves with elasticized cuffs. With an elasticized waist and tie closure, this piece includes flowy leg openings with ruffle trim. Fully lined with moderate stretch.
Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06303-0038
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Strappy Square Toe Block Heels
It's all about proportion with these perfectly balanced strappy sandals. They feature a square toe, slim crisscrossing straps at toe bed, an adjustable buckled ankle strap, and a wide, stabilizing block heel.Sandals are made from a faux leather material.Style Number/Barcode: 07401-0356
Category Name: Vacation Looks
Price: $26.90
Availability: Out of Stock
Product Badge:- Ships Free
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100% That B Script Cap
You're 100% percent that bad b! Rock this sassy baseball cap that features front embroidered text and an adjustable back buckle closure.Style Number/Barcode: 07302-0041
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Mind Your Business Script Cap
Tell 'em, girl. This baseball cap features front embroidery text and an adjustable back buckle closure for the perfect fit. Rock this sassy cap with jeans and a tee for a true IDGAF look!Style Number/Barcode: 07302-0086
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rhinestone Frenzy Earring Variety Pack
Adorn yourself with glamorous gems to make a statement like the diva you are! This variety pack includes 3 large textured hoops with mini rhinestones and an omega back closure. It also includes 9 pairs of luxe studs. Variety pack features rose gold, silver and pearl hues to fit any mood!
Style Number/Barcode: 07001-3967
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tapered Tease High Waist Dress Pants
Dress to impress in trendy dress pants. Transition from office attire to dinner chic in high waist dress pants that feature a cinching tie waist belt with belt loops, structured vertical seams at the waist, a hidden front zipper, and slant pockets. The skinny leg fit leads to a modern tapered fit. Complete outfit with dainty necklace and bracelet for a minimally chic look.
Fits & Feature
- High waist
- Elastic band at back
- Five belt loops, tie waist belt
- Hidden front zipper
- Front hand pockets
- Modern tapered leg fit
- Woven composition offers a natural fit with minimal stretch
Black and Taupe Pants: Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Rust Pants: Model is 5'9" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Olive Pants: Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Burgundy Pants: Model is 5'7" with 32" bust, 25" waist and 36" hips. She is wearing a size small.
Mauve Pants: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Red Pants: Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06402-0977
Category Name: Vacation Looks
Price: $21.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacay Vibes Straw Boater Hat
Get those vacay vibes going as you dress up your tresses! This natural hued straw hat features a boater design and a black hued ribbon trim accent.Style Number/Barcode: 07302-1304
Category Name: Vacation Looks
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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A Star Is Born Earrings
You're a natural born star babe! These earrings are a star shape adorned with rhinestones. They have a post back closure and are open ended. Get your shine on!
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0132
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Totally Grounded Two-Strap Sandal
Equal parts earthy and vibrant, these neon green summer sandals make a statement. Shoes feature double buckle straps with gold-tone hardware, cork-style footbed, and traction sole. Shoe has a textured nylon upper and a faux suede footbed.Style Number/Barcode: 07404-0021
Category Name: Vacation Looks
Price: $11.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Hippie Shake Tie Dye Skirt
The best way to elevate your next maxi skirt? Make it tie dye! Embrace this breezy basic, which features a back zip with hook-and-eye closure, and a wrap front with high slit and waist tie at hip. Skirt is made from pure rayon with minimal stretch. Don't forget to pair it with the matching crop top!Style Number/Barcode: 06301-0031
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance