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 Looks
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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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Compliment Worthy Oval Hoop Earrings
It's easy to look compliment-worthy with these oval hoop earrings that give every outfit a perfect statement! Complete the look in trendy sandals for any occasion.
Fit & Features
- Oval hoops
- Omega closure, rubber stopper
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2022
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Eyes On Me Cat Eye Sunglasses
Catch their gaze and keep it—these cat eyes were made for golden hour snaps and spontaneous weekend plans. Lightweight with just enough edge to own the moment.
Fit & Features
- Metal frame with sleek cat eye silhouette
- Adjustable nose pads
- Slim arms with subtle curve
- Gradient lenses
Style Number/Barcode: 07008-000045
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
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Flirty Aurora Ruffle Lace Crop Top
Capture a flirty aurora in this lace crop top to romance your favorite bottoms! The sleeveless square neckline with ruffle trim adds a touch of charm, while the cropped hem and delicate lace fabric create a playful and feminine look. Complete the look in best-selling bottoms and heels for day or night plans!
Fit & Features
- Lace-lined fabric, no stretch
- Ruffle trim
- Back zipper closure
- Cropped hem
- Runs true to size
Style Number/Barcode: 06003-2434
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Mode Halter Cutout Maxi Dress
Amp up the sultry vibes of your summer 'fits with this sleek knit maxi dress featuring a halter square neck, an asymmetric waist cutout, and a curve-hugging silhouette.
Fit & Features
- Smooth knit fabric with knit lining, high stretch
- Sleeveless square neckline
- Tie-back halter spaghetti straps, partially open back
- Asymmetric side cutout
- Ruching
- Maxi-length form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-000051
Category Name: Vacation Looks
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacay Mode Tropical Print One-Shoulder Maxi Dress
You'll be on vacay mode in this sultry tropical print maxi dress featuring a one-shoulder neckline with a chic O-ring accent and an alluring bust cutout. The floor-length fitted silhouette will flaunt your stunning curves.
Fit & Features
- Mesh fabric, high stretch, knit lining
- Tropical print
- Sleeveless one-shoulder neckline, O-ring accent
- Asymmetric bust cutout
- Asymmetric back strap
- Maxi-length hem, form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-000050
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fun In Floral Lace Mini Dress
So fun in floral print, this lace dress is featured in a form-hugging A-line silhouette and playful mini-length hem. Pair with cute wedge sandals for a cute summer look!
Fit & Features
- Floral print, lace fabric, stretchy knit lining
- Square neck with bust tie
- Adjustable spaghetti straps
- Form-hugging A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6015
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Charming Look Puff Sleeve Ruffled Skater Dress
Create a charming look for weekend brunch in this eyelet knit skater dress with the cutest puff sleeves and ruffled mini-length silhouette!
Fit & Features
- Eyelet knit fabric, stretchy knit lining
- Square neckline
- Short puff sleeves, ruffled hems
- Drop waist
- Tiered ruffled design
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000075
Category Name: Vacation Looks
Price: $9.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Fresh Lace-Trim Linen Cropped Tank Top
Keep your casual summer 'fits fresh with this lace-trim linen cropped tank top. Designed with a lightweight linen-blend fabric, this top is perfect for creating effortless everyday looks. It features a low V-neckline accented with a tie-front design leading to a center front slit, tank shoulder straps, a dainty eyelet lace trim for a soft girl vibe, and a fitted cropped hem. Style with light-wash denim and a layered necklace.
Fit & Features
- Linen-blend fabric with woven lining, no stretch
- V-neckline, tie-front design, center front slit
- Tank straps
- Eyelet lace trim
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06003-2384
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lively Elegance Smocked Floral Babydoll Dress
You'll fall in love with this breezy floral babydoll dress, so adorable for weekend parties and graduations! With its stretchy smocked bodice and adjustable straps, you'll get the perfect fit. The chiffon fabric and pretty floral print add a touch of elegance to the playful babydoll silhouette and ruffled short-length hem.
Fit & Features
- Floral printed chiffon fabric, stretchy knit lining
- Square neckline
- Stretchy smocked bodice
- Adjustable spaghetti straps
- Babydoll silhouette
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 05102-6062
Category Name: Vacation Looks
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Got The Look Sleek Aviator Sunglasses
Get a coveted cool-girl look in these sleek aviator sunglasses! They feature a metal frame, tinted lenses, rubber nose supports, and a comfortable fit. Complete the look in a cool denim jacket.
Fit & Features
- Metal frame
- Tinted lenses
- Rubber nose supports
- Comfortable fit
Style Number/Barcode: 07008-1080
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Forever Chic Sleeveless Wrap Mini Dress
You'll look forever chic in this sleeveless wrap mini dress perf for everyday styling! Designed with a stretchy brushed knit fabric, it features a double-lined design at the top for added coverage. The mini-length dress is shaped with a square neckline, thin tank shoulder straps, a faux wrap-front with the cutest tie detail at the waist, and a form-hugging fit to showcase your curves. Pair with slip-on sandals.
Fit & Features
- Stretchy brushed knit fabric, double-lined top
- Square neckline
- Tank straps
- Faux wrap-front with tie detail
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5761
Category Name: Vacation Looks
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Instincts Halter Cutout Leopard Mesh Midi Dress
Elevate your fierce style in this leopard mesh midi dress for a chic cocktail bar. Adorned with a chain-trimmed halter strap, this dress features a sultry cutout bodice with a hoop insert and ruffled trim slit that shows some skin.
Fit & Features
- Leopard floral print, mesh fabric, sewn-in knit lining
- Cowl halter neckline, chain trim, spaghetti strap tie
- Cutout bodice, hoop insert
- High side ruffled slit
- Form-hugging silhouette, midi-length hem
- Runs true to size
Style Number/Barcode: 05103-000465
Category Name: Vacation Looks
Price: $17.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE
Available Size: L, XL
Product Badge:- Sale
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Flawless Beauty Eyelet A-Line Mini Dress
Make every heart flutter in this eyelet mini dress boasting a flirty bust tie and flattering A-line silhouette. Perfect for shower celebrations or brunch!
Fit & Features
- Eyelet knit stretchy fabric, stretchy knit lining
- V-neckline, spaghetti straps
- Bust tie
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6037
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Elevated Trend Ribbed Knit Tube Crop Top
Elevate the trends in this ribbed knit tube top perfect for off-duty days! Designed with a trendy strapless neckline with sleek metal hardware. The form-hugging design flatters your figure while the cropped hem adds a touch of sass. Complete the look in high-rise cargo pants.
Fit & Features
- Stretchy ribbed knit fabric
- Metal hardware insert
- Form-hugging
- Cropped hem
- Runs true to size
Style Number/Barcode: 06005-1920
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beachside Trend Checkered Straw Bucket Hat
From summer beach days to vacays, this checkered straw bucket hat will be your favorite sunny day essential! It features a convenient inner adjustable strap with velcro closure for a perfect snug fit. Complete the look in sandals.
Fit & Features
- Checkered pattern
- Straw material
- Inner adjustable strap with velcro closure
- Bucket hat style
Style Number/Barcode: 07302-1628
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Darling Vibe Ditsy Floral A-Line Midi Dress
Look oh-so-darling at weekend brunch in this ditsy floral A-line midi dress! The sleeveless sweetheart neckline is detailed with a dainty lace trim and tie-front design.
Fit & Features
- Woven fabric
- Ditsy floral print
- Sleeveless sweetheart neckline, dainty lace trim, lace trim spaghetti straps
- Tie-front detail, underbust seam
- Midi-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5989
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Charming Floral Chiffon Lace Trim Skater Dress
Charm them all with your pretty flair in this breezy floral chiffon lace trim skater dress! Designed with an airy sheer floral chiffon fabric with a dainty eyelash lace trim, this short dress is the effortlessly chic style you need for parties. The bodice is shaped with a sweetheart neckline with ruching at the bust and adjustable spaghetti straps with ruffled flutter sleeves for a sweet feminine vibe. The fitted waist is accented with an open tie-back design, leading to a flowy skater skirt with an A-line silhouette. Complete the look with hoop earrings and espadrille wedges.
Fit & Features
- Sheer floral chiffon fabric, woven lining with eyelash lace trim, no stretch
- Ruched sweetheart neckline
- Adjustable spaghetti straps with ruffled flutter sleeves
- Open tie-back design
- Lower zipper with hook and eye closure
- A-line fit
- Runs true to size
Style Number/Barcode: 05101-3154
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect Vacation Long Sleeve V-Neck Cutout Mini Dress
This V-neck mini dress pairs perfectly with your next vacation or pool party! This playful and stylish dress features long sleeves with flare cuffs, a V-neckline with a hoop insert, and cutout details on the bodice and back. Its bodycon fit and mini-length hem will highlight your curves while you explore exotic destinations or the resort bar! Complete the look with sunnies.
Fit & Features
- Texture knit fabric, sewn-in knit lining, minimal stretch
- V-Neckline with hoop insert
- Cutout bodice and back
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5705
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cute Vibes Flower-Detail Espadrille Wedges
You'll love the cute vibes of these flower-detail espadrille wedges! Designed with a trendy espadrille wedge sole, they feature a closed almond toe made with a denim-like material and an adorable flower cutout design perfect for the summer season. They have a partially closed back and straps that lace up the leg with a tie closure for a fabulous look. Style with your fave sundress for a weekend party!
Fit & Features
- 3.5" Wedge heel
- Espadrille sole
- Closed almond toe
- Denim-like material, flower cutout design
- Partial closed back, lace-up straps with tie closure
- Padded faux leather insole
- Runs true to size
Style Number/Barcode: 07406-0351
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropical Vibes High Slit Wrap Maxi Skirt
Give off major tropical vibes whether you're jet-setting to a dreamy oasis or headed to a weekend getaway in this printed maxi skirt! The stretchy knit fabric showcases a bold contrasting tropical print for a stylish allure, and includes a built-in knit brief for coverage. The skirt features a high-rise elasticized waist, a wrap-front design creating a sultry high slit, and a flowy A-line fit on the maxi-length silhouette. Pair with a basic tank top and strappy sandals.
Fit & Features
- Stretchy knit fabric, built-in knit brief
- Tropical print
- High-rise elasticized waist
- Wrap-front design, high slit
- A-line fit
- Runs true to size
Style Number/Barcode: 06501-0966
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Main Feed Moment Denim Mini Skort
Classic with a modern twist, this denim mini skort brings Y2K vibes in a trending silhouette! Style with a graphic top for any casual plans.
Fit & Features
- Medium wash non-stretch denim, knit shorts lining
- Mid-rise waist
- Seam front detailing, form-hugging fit
- Mini-length hem
- Front button tab and hidden zipper closure
- Three-pocket styling, belt loop accents
- Runs true to size
Style Number/Barcode: 06603-000025
Category Name: Vacation Looks
Price: $11.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: MED, DENIM
Available Size: S, L
Product Badge:- Sale
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Pretty Presence Floral Lace Trim Crop Top
Charm them with your pretty presence in this floral lace trim crop top! The airy sheer mesh fabric is detailed with a blooming floral print for the sweetest vibes. The top features a sleeveless V-neckline, spaghetti straps, a dainty lace trim in a criss-cross design, ruffled overlays for a flirty flair, and a cropped hem. Style with high waist denim shorts and slip-on sandals for casual weekend plans.
Fit & Features
- Floral print
- Stretchy sheer mesh fabric, knit top lining
- V-neckline, spaghetti straps
- Lace trim
- Ruffled overlays
- Cropped hem, lettuce edge trims
- Runs true to size
Style Number/Barcode: 06001-5290
Category Name: Vacation Looks
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fantastic Sparkle Rhinestone Strappy Flat Sandals
Rhinestone-embellished straps boast a fantastic sparkle to these glam sandals! They feature an almond toe, a strappy design, and a flat faux leather sole with rhinestone embellished trim for extra shimmer. Complete the look with a luxe purse for any occasion!
Fit & Features
- Flat faux leather sole, rhinestone embellished trim
- Almond toe
- Rhinestone embellished strappy design
- Runs true to size
Style Number/Barcode: 07404-1194
Category Name: Vacation Looks
Price: $12.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Day Ruffled Ditsy Floral Skater Dress
You'll love every moment spent in this ditsy floral skater dress! The square neckline and spaghetti tie straps add a flirty touch, while the stretchy smocked bodice ensures a comfortable fit. With a playful ruffled skater silhouette and a mini-length hem, this dress is perfect for any occasion. Complete the look in wedges.
Fit & Features
- Ditsy floral print, woven fabric lined with knit
- Spaghetti tie strap
- Square neckline
- Ruffled skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5425
Category Name: Vacation Looks
Price: $20.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale