Vacation Looks
Vacation outfits should feel as effortless as your out-of-office vibe. Think long floral dresses that move with the breeze, easy cover-ups for poolside lounging, and bold two-piece sets that pop in every photo. From beachy maxis that bring instant elegance to denim shorts that nail casual cool, each piece blends comfort with style so you never have to choose between the two. These looks are made for packing light, looking chic, and serving up Instagram-worthy vacation moments.
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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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Effortless Style Short Sleeve Ribbed Knit Crop Top
This adorable short sleeve crop top will make everyday styling effortless. Made with stretchy double-lined ribbed knit, it features a classic crew neckline, short sleeves, and a fitted cropped hem. The perf basic, pair with straight-leg jeans and sneakers.
Fit & Features
- Stretchy double-lined ribbed knit fabric
- Crew neckline
- Short sleeves
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06002-1859
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everyday Chic Cutout Sandals
Bringing effortless energy wherever you go. These chic slide sandals are your no-brainer pick for sun-soaked strolls, coffee runs, and last-minute plans.
Fit & Features
- Square toe
- H-shaped band
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-000038
Category Name: Vacation Looks
Price: $19.90
Availability: In Stock
Available Color: WHITE
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Just Your Stripe Off-The-Shoulder Crop Top
This striped crop top is just what you're looking for! It's designed on stretchy rib knit fabric with a trendy striped print, an off-the-shoulder neckline to bare some skin, and a flirty cropped hem. Complete the look in denim shorts for casual plans.
Fit & Features
- Striped rib knit stretchy fabric
- Off-the-shoulder neckline
- Cropped hem
- Runs true to size
Style Number/Barcode: 06005-1972
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Radiant Accent Floral Boho Satin Scarf
The perfect satin scarf to give your outfit a radiant accent! The silky satin woven material is designed with a vibrant floral bohemian-inspired print for a trendy allure. Style this scarf as a pretty headwrap, around your neck, or tied on your bag as a chic accent! Complete the look with a sleek choker necklace.
Fit & Features
- Silky satin woven material
- Floral bohemian print
- Multiple ways to style and wear
Style Number/Barcode: 07305-0495
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: MULTI
Available Size: NS
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Shine On Me Layered Disc Belly Chain
Just a lil sparkle to catch the light (and compliments). This delicate layered belly chain brings the shine with dainty disc details and major stacking potential.
Fit & Features
- Layered chain silhouette
- Mini disc charms
- Adjustable lobster clasp closure
Style Number/Barcode: 07002-000098
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
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Shade Shift Leopard Square Sunglasses
Block the rays, not the slay. These square sunglasses serve retro energy with a modern edge—aka your new go-to for every vibe.
Fit & Features
- Leopard pattern
- Square frame
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000080
Category Name: Vacation Looks
Price: $10.90
Availability: In Stock
Available Color: LEOPARD
Available Size: NS
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Catch Flights Crochet Sweater Topper
She’s giving jet-setter vibes with just a touch of drama. Layer this crochet sweater topper over your fave tanks or dresses when your outfit needs a little extra flirt.
Fit & Features
- Sheer crochet knit fabric
- Long sleeves with flare cuffs
- Boat neckline
- Ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06005-000105
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Feel The Vibes Halter V-Neck Crop Top
Get ready to feel the vibes of this elevated basic halter V-neck crop top! It's perfect for styling with any bottoms.
Fit & Features
- Smooth knit, cotton-blend, stretchy fabric
- Halter V-neck
- Crop hem
- Runs true to size
Style Number/Barcode: 06002-000346
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: BLACK, WHITE, DARK, DENIM, BROWN
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Chase The Sun Lace-Up Espadrille Wedges
Flaunt a sunny day style in these lace-up espadrille wedges perfect for a beach day, backyard bbq, or vacation!
Fit & Features
- 4" wedge heel
- Almond toe, curved band
- Lace-up ankle straps
- Platform wedge heel
- Runs true to size
Style Number/Barcode: 07406-0364
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: NATURAL
Available Size: 7, 10
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Dancing Moves High-Rise Side Ruffle Midi Skirt
Dance all night in this midi skirt featuring a flattering high-rise waist, form-hugging silhouette, and a high side slit with a flirty ruffled trim perfect for styling with heels. The smooth knit fabric hugs your curves and offers plenty of stretch.
Fit & Features
- Smooth knit-lined stretchy fabric
- High-rise waist
- High-side slit with ruffle trim
- Form-hugging
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06501-1063
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feeling Daring Texture Knit Mini Skirt
Feel daringly stylish with this mini skirt! This ultra-trendy skirt features a high-rise waist, a bodycon silhouette, and a flirty mini-length hem on texture knit fabric. Dare to stand out and shop the matching top to complete the look!
Shop Matching Top: Feeling Daring Texture Knit Crop Top
Fit & Features
- High-rise waist
- Bodycon silhouette
- Mini-length hem
- Texture knit fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 06501-0949
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- High-rise waist
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Spill The Secrets Abstract Print Halter Top
For when your outfit's louder than your group chat. This abstract print mesh halter top is light, effortless, and made for catching stares you weren’t even trying for.
Fit & Features
- Mesh fabric, high stretch
- Abstract print
- Sleeveless plunge V-neckline
- Tie-front detail under the bust, front flyaway design
- Halter spaghetti straps, tie-back design, partially open back
- Mid-length hem, flowy fit
- Runs true to size
Style Number/Barcode: 06001-000162
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
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Set For Good Cap Sleeve Slit Texture Crop Top
You'll be set for good in this stylish texture crop top all season! Featuring adorable cap sleeves, a V-neckline, and an adjustable bust drawstring atop a flirty slit along the cropped hem. Complete the look with the matching bottoms.
Shop Matching Bottoms: Set For Good High Rise Texture Mini Skirt
Fit & Features
- Texture sheer fabric, bust lining, minimal stretch
- Cap sleeves
- V-neckline
- Adjustable bust drawstring, center slit
- Cropped length
- Runs true to size
Style Number/Barcode: 06001-5287
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ruffle Me Up Midi Skirt
Flirty, flowy, and made for vacay vibes! This ruffle-trim midi skirt brings soft drama with a sleek fit and side slit that shows just enough—pair it with the matching top to complete the look.
Shop The Matching Top: Ruffle Me Up Crop Top
Fit & Features
- Smooth double-lined stretchy knit fabric
- High-rise waist
- Side ruched seam and ruffled slit
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06501-000060
Category Name: Vacation Looks
Price: $28.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Girlycore Floral Puff Sleeve Crop Top
Channel a cute girlycore vibe with this floral puff sleeve crop top! Detailed with a dainty floral print, this top features a sweetheart neckline, a ruched bust with an adjustable drawstring, adorable short puff sleeves, a smocked back for added stretch, and a cropped hem with a flirty ruffled trim. Style with high-rise jeans and sandals.
Fit & Features
- Dainty floral print
- Woven fabric, front knit lining, minimal stretch
- Sweetheart neckline, ruched bust with adjustable drawstring
- Short puff sleeves, elastic cinched hems
- Smocked back
- Ruffled cropped hem
- Runs true to size
Style Number/Barcode: 06003-2533
Category Name: Vacation Looks
Price: $13.97 $32.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L, XL
Product Badge:- Sale
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Sun-Kissed Moments Tie-Strap Bikini Bottoms
You'll have sun-kissed moments in these trendy low-rise bikini bottoms featuring tie straps on each side with beaded detailing. Style with the matching bikini top.
Shop Matching Top: Sun-Kissed Moments Triangle Bikini Top
Fit & Features
- Nylon-blend fabric, high stretch
- Low-rise waist
- Tie straps on each side, beaded details
- Cheeky fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000009
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Nylon-blend fabric, high stretch
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Sweet Talk Floral Mesh Maxi Dress
Soft and flirty for wherever the day takes you. With lace trim and a body-skimming fit, this floral mesh maxi dress is your go-to for brunch plans and weekend dates!
Fit & Features
- Floral print, mesh fabric, stretchy knit lining
- Crochet lace trim V-neckline
- Spaghetti straps
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000325
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
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Chic Beauty Strappy Back Knit Midi Dress
This chic sleeveless midi dress is designed with a jacquard patterned sweater knit fabric and features a square neckline, halter spaghetti straps, and a bold open back with cross-back straps and tie-back straps. The midi-length form-hugging silhouette is detailed with a high front slit.
Fit & Features
- Knit fabric with jacquard pattern, moderate stretch
- Square neckline, halter spaghetti straps
- Open back, cross-back straps, tie-back straps
- Contrast seam design at the bodice
- High front slit
- Midi-length form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-2227
Category Name: Vacation Looks
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Admiring Looks PVC Platform Mules
From casual outings to formal soirees, these platform mules are sure to receive admiring looks! Designed with clear PVC straps that offer a modern, barely-there look, these block heel mules add a chic edge to every look.
Fit & Features
- 3.5" Block heel
- Square toe
- Clear PVC straps
- Luxe fit cushioned insole
- Platform sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-000327
Category Name: Vacation Looks
Price: $43.90
Availability: In Stock
Available Color: NUDE-2
Available Size: 5.5, 6.5, 7, 7.5, 8.5, 9, 10
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Coastal Cutie Faux Pearl Charm Bracelet
Catch coastal cute vibes with this bracelet! It's stacked with seashells, starfish, and playful charms along with faux pearls made for your next vacay or summer party.
Fit & Features
- Seashell, starfish, and various charms
- Faux pearls
- Stretchy fit
Style Number/Barcode: 07003-000086
Category Name: Vacation Looks
Price: $3.97 $7.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Here Comes The Sun Strapless Ruffled Mini Dress
Here comes the sun and you radiating trendy vibes in this strapless mini dress perf for casual plans! The ruched sides and ruffled hem add a playful touch to the bodycon silhouette.
Fit & Features
- Double-lined brushed knit fabric, moderate stretch
- Strapless straight neckline
- Ruched side seams
- Bodycon silhouette
- Mini-length tiered ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5922
Category Name: Vacation Looks
Price: $19.97 $32.90
On Sale: Yes
Availability: In Stock
Available Color: YELLOW, BROWN
Available Size: XS, L, S, M
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Bangle Princess Five-Pack Bracelet Set
Add a chic finishing touch to your look with this five-pack bangle bracelet set. This stunning collection features five uniquely designed bangles that effortlessly stack together or make a statement worn separately.
Fit & Features
- Five-pack bangle bracelet set
- Various styles and designs
Style Number/Barcode: 07003-000034
Category Name: Vacation Looks
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
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Cutest Vision Chain Link Trim Sunglasses
Any on-trend, sunny day look isn't complete without these sunglasses! They feature angular square-tinted lenses, rubber nose supports, and chain-link accent arms. Complete the look in sandals.
Fit & Features
- Angular square-tinted lenses
- Rubber nose supports
- Chain-link accent arms
Style Number/Barcode: 07008-1094
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunny Daze Linen Tie-Front Crop Top
Catch the breeze, catch the vibe. This linen tie-front crop top is made for sunny days and carefree moments—easy, airy, and ready for wherever the day takes you.
Shop Matching Bottoms: Sunny Daze Linen Mini Skort
Fit & Features
- Linen woven fabric
- Sleeveless V-neckline
- Tank shoulder straps
- Tie-front design
- Fitted ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06204-000023
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Part of a Set