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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Smocked Over You Ruffled Top
We can't get over how gorge this smock trend is! Pair top with your fav high rise pants for the perf look!
Fit & Features
- Square Neckline
- Adjustable Spaghetti Straps | Removable
- Smocked Bodice
- Ruffled Hem
- Lightweight woven fabric
- Relaxed Fit
- Moderate Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06001-2451
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Florals Tie Front Top
Keep it flirty in florals this season babe! Wrap yourself in this head-turning tie front top! Don't forget to add the matching skirt to complete your look!
Shopping Matching Skirt: Flirty Florals Pencil Skirt
Fit & Features
- Tie Front Bodice
- Long Sleeves
- Floral Print
- Brushed Knit Fabric
- Relaxed Fit
- Moderate Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 06202-0053
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flirty Florals Pencil Skirt
Keep it flirty in florals this season babe! Wrap yourself in this head-turning skirt! Don't forget to add the matching top to complete your look!
Shop Matching Top: Flirty Florals Tie Front Top
Fit & Features
- High Waist
- Floral Print
- Brushed Knit Fabric
- Mini Skirt Length Knit Lining
- Relaxed Fit
- Moderate Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 06501-0155
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Breezy Chic Belted A-Line Maxi Dress
Breezy chic, this A-line maxi dress is made with an airy gauze woven fabric accented with sheer lace insets. The belted waist leads to a long tiered flowy fit for that effortless vibe.
Fit & Features
- Gauze woven fabric with sheer lace insets
- Strapless sweetheart neckline with ruffled trim
- Bust cutout with tie-front detail, ruching, underbust seam
- Faux leather belted waist, gold metal buckle
- Maxi-length hem
- Tiered A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-6106
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Like Me Puff Sleeve Crop Top
This adorable top is so sweet - just like you! Pair with your fave denim for an effortlessly chic look.
Fit & Features
- Off the shoulder sweetheart neckline
- Wrap front | Pleated details
- Hidden back zipper closure
- Long puff sleeves with single buttons to cuff
- Cropped, banded hem
- Woven fabric | No stretch
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06003-0721
Category Name: Vacation Looks
Price: $14.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sun-Kissed Cutie Halter Plunge Flowy Romper
Turn heads in this romper at backyard BBQs and parties! This romper boasts a sultry plunge halter neckline, a trendy flowy silhouette that moves beautifully with every step, creating an effortlessly chic look.
Fit & Features
- Swiss dot woven fabric, woven shorts lining
- Plunge halter neckline, dual spaghetti strap tie
- Stretchy smocked waist
- Flowy hem
- Runs true to size
Style Number/Barcode: 06303-000020
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spring Ready Vibes Crop Top
Get all those spring ready vibes going in this adorable twist detail crop! Pair the top with a denim mini for a fresh and fun look.
Fit & Features
- Short puff sleeves with ruffle trim
- Deep V neckline
- Twist front detail
- Tie back closure
- Cropped
- Stretchy knit fabric
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06001-2445
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Classic Beauty Faux Leather Purse
You're a classic beauty who loves a sophisticated look! This chic bag is a must for you.
- Rectangular structure
- Top handle with gold accents
- Fold over design + snap closure
- Detachable matching shoulder strap
- Faux leather
- Single inner open pocket
Style Number/Barcode: 07203-0193
Category Name: Vacation Looks
Price: $12.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ambitious Af Faux Leather Cross-Body Purse
Baby you are ambitious af, and you are on the go! This is the perfect go-to faux leather bag for the essentials of a busy boss babe!
- Rectangular structure
- Square flap closure
- Detachable chain shoulder strap
- Faux leather
Style Number/Barcode: 07203-0197
Category Name: Vacation Looks
Price: $12.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wide Awake Ribbed Pajama Tank And Shorts
Wide awake and ready for a slumber party with a cute ruffle pajama set! Don't even get us started on how cute this set would look on matching bridesmaids!
- Two piece set
- Tank straps
- Scoop neckline
- Faux buttons down the center
- Cropped hemline
- Ribbed material | Moderate stretch
Model is 5'9" with 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 07103-0308
Category Name: Vacation Looks
Price: $13.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sporty Spice Velcro Strap Sandals
Embody your sporty side this summer when you slip into these strappy sandals, and a pair of flowy high waist pants!
- Open round toe
- Flat sole | Short platform
- Woven straps | Velcro closure
- Faux leather lining
Style Number/Barcode: 07404-0121
Category Name: Vacation Looks
Price: $11.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Hexagon Rhinestone Drop Hoop Earrings
Add a touch of shine to your look in a unique way with a pair of drop hoops!
- Double hexagon outline
- Encrusted in rhinestones
- Drop hoop design
- Post back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0368
Category Name: Vacation Looks
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Distressed Diva Denim Shorts
Bring the fringe with these festival-ready shorts, perfect to pair with your fav graphic tees!
Fit & Features
- High Rise Waist
- Single Button | Zipper Closure
- Traditional Five Pocket Design
- Frayed Hem
- Denim Fabric
- Light Wash
- Relaxed Fit | Minimal Stretch
Style Number/Barcode: 06603-0070
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Go To Double O Ring Belt
Double up your accessory game with this stylish belt! It features a narrow faux leather belt and a double O ring buckle.
Model is 5'9" with a 31.5" bust, 24.5" waist and 35.5" hips.
Style Number/Barcode: 07301-1084
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Feeling Chiffon Off Shoulder Mini Dress
Bloom, baby! Look absolutely stunning in this floral mini dress!
Fits & Features
- Adjustable Shoulder Straps
- Off Shoulder Neckline & Sleeves
- Layered Ruffles Along Neckline & Hem
- Mini Length Silhouette
- Chiffon Fabric I Lining
- Form Hugging Fit I Minimal Stretch
Style Number/Barcode: 05101-0434
Category Name: Vacation Looks
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bermuda Babe High Rise Shorts
Kick off the season with a pair of classic bermudas to show off glowing gams! Pair with stylish slides to complete your look!
Fit & Features
- High Rise Waist
- Single Button And Zipper Closure
- Traditional Five Pocket and Belt Loop Design
- Bermuda Length | Raw Edge Hem
- Denim Fabric
- Relaxed Fit
- Moderate Stretch
Model is 5'9" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06603-0061
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Not So Typical Cubic Zirconia Bollo Bracelet
Babe your style is not so typical, it's original and high end, and that's why this is the bracelet for you! Layer with your gold watch for a real classy vibe!
- Circular cubic zirconia stones
- Adjustable bollo closure
- Dainty rope chain
Style Number/Barcode: 07003-0081
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sherpa Lounge Crop Top
This cozy top has us in our feels! Throw on this cute sherpa piece for those perfect lazy Sundays bby!
Shop Matching Shorts: Sherpa Lounge Drawstring Shorts
Fit & Features
- Off The Shoulder Neckline | V-Neck Bust
- Long Sleeves
- Cropped Hem | Ribbed
- Lined Sherpa Fabric
- Relaxed Fit
- Minimal Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 07103-0302
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sway With Me Halter V-Neck Paisley Skater Dress
This breezy skater dress brings the romance with a halter neckline and swingy silhouette made to float with you. Perfect for golden hour snaps, weekend wandering, or spontaneous getaways!
Fit & Features
- Paisley print, woven fabric, bust lining
- Halter V-neckline with spaghetti strap ties
- Stretchy smocked bust
- Tie back design
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5575
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sherpa Lounge Drawstring Shorts
These cozy shorts have us in our feels! Throw on this cute sherpa piece for those perfect lazy Sundays bby!
Shop Matching Top: Sherpa Lounge Crop Top
Fit & Features
- Mid Rise Waist
- Drawstring Waist
- Lined Sherpa Fabric
- Relaxed Fit
- Minimal Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 07103-0303
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tori Floral Chiffon A-Line Dress
Spring forward in our twirl-worthy Tori dress! Her all over floral print on sheer chiffon fabric will make for a stunning look.
Fit & Features
- Adjustable spaghetti straps | Cross back
- Plunging wrap front V neckline
- High waist
- Back zipper | Hook and eye closure
- Flowy sheer A-line chiffon skirt | Short knit lining
- Floral print
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-0664
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Come Away With Me Puff Sleeve Linen Top
Come away with me, to another place, where we can sip on mimosas and take pics in our cute linen sets!
Fit & Features
- Square neckline
- Puff sleeves
- Cropped neckline
- Tassel fringe hemline
- Composed of linen | Minimal stretch
- Zipper closure center back
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-0703
Category Name: Vacation Looks
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Come Away With Me Cotton Skort
Come away with me, to another place, where we can sip on mimosas and take pics in our cute cotton sets! The skort features a high-rise waist, a wrap front overlay, a tassel fringe trim, and a back zipper closure on cotton fabric with a knit lining. Complete the look with the matching crop top.
Shop Matching Top: Come Away With Me Cotton Crop Top
Fit & Features
- High-rise waist
- Wrap front with tassel fringe
- Skort-style design
- Back zipper closure
- Cotton fabric, knit lining, no stretch
- Runs true to size
Style Number/Barcode: 06303-0210
Category Name: Vacation Looks
Price: $6.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bow Knows Studded Jelly Sandals
Toeing that line between covetably cute and totally chic, these jelly sandals easily elevate summer looks. Sandals feature a classic thong construction and bow embellishment with rose gold pyramid studs at toe. Sandals are flat and made from a PVC material.Style Number/Barcode: 07404-0086
Category Name: Vacation Looks
Price: $12.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free