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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Knot Tonight Drape Mini Dress
Go for maximum drama in this eye-catching mini! Dress features a deep V neckline, a draped bodice with knot detail at middle and an elasticized back, long bell sleeves, and a gently pleated flared mini. Dress is made from a lightly textured crepe-like blend with moderate stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0164
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Perfectly Stylish Sleeveless Ribbed Knit Midi Dress
Achieve a perfectly stylish everyday look with this sleeveless ribbed knit midi dress! Designed with a comfortable ribbed knit fabric offering plenty of stretch, it features a V-neckline, spaghetti straps, a midi-length hem with a chic high front slit, and a form-hugging silhouette. Pair with a cropped denim jacket and clear mules.
Fit & Features
- Stretchy ribbed knit fabric
- V-neckline
- Spaghetti straps
- High front slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-1645
Category Name: Vacation Looks
Price: $38.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Hot Catch Fishnet Tights
The perfect layered-look accessory, these fishnet tights pair perfectly with ripped denim or combat boots and a mini dress. Mesh tights have an extra-large jacquard weave and an elasticized waist. Tights are made from nylon and offer moderate stretch.
Fit & Features
- Extra-large jacquard weave
- Elastic waist
- Nylon fabric
- Moderate stretch
Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07305-0035
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Newsgirl Cabby Hat
Extra, extra, read all about your stylish new hat! This newsboy-inspired cap features braided trim with button detail.Style Number/Barcode: 07302-0094
Category Name: Vacation Looks
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Goldi Lock Pendant Necklace
A statement-making lock pendant anchors this otherwise dainty gold-tone necklace. It features a lightweight linked chain with an adjustable lobster clasp closure.Style Number/Barcode: 07002-0158
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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On Lock Lobster Claw Necklace
Whether it's your BF, your BFF, or your heart—keep it on lock! Show 'em with this statement-making gold-tone necklace. It features a lock-and-ring pendant, and oversize lobster-clasp closure, and medium-size chain links.Style Number/Barcode: 07002-0159
Category Name: Vacation Looks
Price: $5.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Live It Up In Linen Midi Dress
Live it up in this absolutely adorable ditsy floral printed midi! The dress features a sleeveless bodice, tie shoulder spaghetti straps, a sweetheart neckline with pleated detailing and a tie front, and a hidden back zipper and hook and eye closure. The dress is composed of a linen fabric with a shorter woven lining and has no stretch.Style Number/Barcode: 05102-0305
Category Name: Vacation Looks
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Hippie Shake Tie Dye Top
The best way to elevate your next crop top? Make it tie dye! Embrace this breezy basic, which features adjustable spaghetti straps, a smocked back, and a tie-front bust with key hole detail and hook-and-eye closure. Top is made from pure rayon with minimal stretch. don't forget to pair it with the matching maxi wrap skirt!Style Number/Barcode: 06003-0290
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Life's A Beach Mesh Dress
Hit the pool, bask by the beach, or prep to party in this colorful mesh maxi! Dress features a vibrant tropical print in turquoise, blue, and rust, a strapless neckline, dramatic ruffle trim running from bust to hem, a high front slit, and built-in briefs. Dress bodice is semi-sheer and does not include a top. Maxi is made from a mesh blend material with moderate stretch.Style Number/Barcode: 05102-0286
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual Chic Tie Front Top
Casual chic is the way to go with this adorable tie front top. It features a long lapel collar, long sleeves with elastic cuffs, a tie front closure creating a deep V neckline, and a cropped hem. The top is composed of a lightweight, airy textured woven fabric with no stretch.Style Number/Barcode: 06204-0125
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ribbon Wave Fabric Headband
Go for statement style with this chic headband! It features a flexibly structured, pleated fabric-covered crisscross design and a faux suede underlay. One size fits most.
Style Number/Barcode: 07006-0048
Category Name: Vacation Looks
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Heart Eye Sunglasses
You'll totally have heart eyes for these fab sunnies! They feature a heart shaped cat eye design with a white plastic frame and black lenses.
Style Number/Barcode: 07008-0473
Category Name: Vacation Looks
Price: $7.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glitzy Glitter Duffle Bag
You're so extra and glam, so you need a bag that fits your personality! This duffle features a top zipper closure, top handles, and an adjustable shoulder strap. The interior features a single zippered pocket. The bag is composed of a faux leather material with a quilted fine glitter design.Style Number/Barcode: 07203-1891
Category Name: Vacation Looks
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fave Fanned Out Tassel Earrings
These fanned out tassel earrings will become your new faves for sure! They feature a round post with a post back closure attached to an open circular piece with a half moon below, accented with fanned out tassels.Style Number/Barcode: 07001-4472
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Net Shopper Bag
Get ready for a day full of shopping with this adorable net shopper bag! It features a lightweight sheer netted design with top handles.Style Number/Barcode: 07203-0049
Category Name: Vacation Looks
Price: $4.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Center Stage High-Rise Acid Denim Skort
Take center stage in this acid denim skort to rock out at concerts or festivals! Made from a denim fabric with an edgy acid wash rinse, this skort features a flattering high-rise waist, a front envelope skirt overlay for added flair, and a form-hugging mini silhouette. Complete the look in a cute strapless top and boots.
Fit & Features
- Acid wash rinse, denim fabric, slight stretch
- High-rise waist
- Front envelope skirt overlay, form-hugging
- Front button and hidden zipper closure
- Back pockets
- Runs true to size
Style Number/Barcode: 06603-0356
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bebesita Baseball Cap
You can be my bebesita. This hat says it all. The hat features a baseball cap design, a script graphic that reads: "Bebesita" in a contrasting hue and an adjustable back with metal hardware.Style Number/Barcode: 07302-0007
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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3 Row Layered Charm Necklace
Layer on this pretty charm necklace for a trendy chic vibe! It features three rows, the two shorter layers featuring snake chains, and the longest layer showcasing a moon and star charm with cubic zirconia details. Includes an adjustable lobster clasp closure.Style Number/Barcode: 07002-5189
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bringing The Luxe Necklace
Bring the luxe to your look with this necklace! It features a single row of textured geometric emblems and a dainty chain with lobster clasp closure.Style Number/Barcode: 07002-5201
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rhinestone Cross Charm Hoops
Play up your pretty 'fit with these cross charm hoops! The earrings feature a thin metal hoop with a rhinestone adorned mini cross charm. Includes an omega closure.Style Number/Barcode: 07001-4468
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Newsgirl Cabby Hat
Extra, extra, read all about your stylish new hat! This newsboy-inspired cap features braided trim with button detail.Style Number/Barcode: 07302-0092
Category Name: Vacation Looks
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flower Bomb Ruffled Top
Part flamenco, part casual chic, this floral smocked top gives us serious summer vibes! It features a strapless bodice with ruffle trim at bust and hem and a smocked middle. Top slips on and is made from a lightweight rayon with minimal stretch.Style Number/Barcode: 06003-0253
Category Name: Vacation Looks
Price: $4.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Such A Beauty Mini Dress
Girl, you're such a beauty, and this classically chic mini dress will make for the perfect 'fit. It features a sleeveless bodice, a V-neckline with a tie ruched bust detail, adjustable spaghetti straps, a square back with a hidden zipper and hook and eye closure, a trendy waist front cutout with a tie ruched detail, and a flowy skirt with an adorable ruffled mini-length hem. The short dress is composed of a woven fabric with minimal stretch. Style with a cute pair of mules.
Fit & Features
- Sleeveless bodice, V-neckline, tie ruched bust
- Adjustable spaghetti straps
- Square back, hidden zipper, hook and eye closure
- Waist front cutout, tie ruched detail
- Flowy skirt, ruffled mini-length hem
- Woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-0263
Category Name: Vacation Looks
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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On Knit Mini Dress
You're always on it when it comes to style, and this basic knit mini will make for such a cute 'fit. The dress features a sleeveless bodice, tank-like shoulder straps, a square neck and back, and a short, form hugging fit. The dress is composed of a soft knit that offers plenty of stretch.Style Number/Barcode: 05102-0095
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free