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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Wild Stride Suede Leopard Sneakers
Step into your fierce era. These leopard micro suede side stripe sneakers blend bold vibes with everyday comfort—perfect for casual hangs or making errands a little extra.
Fit & Features
- Round toe
- Low-top silhouette
- Side stripe faux leather accent
- Lace-up closure
- Cushioned insole, rubber sole
- Micro faux suede material, leopard print
- Runs true to size
Style Number/Barcode: 07407-000001
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: In Stock
Available Color: LEOPARD
Available Size: 5.5
Product Badge:- Sale
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Style Upgrade Blue Light Glasses
Your screen time just got a style upgrade. These square blue light glasses keep things sharp while helping filter blue light, perfect for work days, study sessions, and late-night scrolling.
Fit & Features
- Square-shaped plastic frame
- Built-in nose pads
- Clear blue-light lenses
Style Number/Barcode: 07008-000113
Category Name: Vacation Looks
Price: $11.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
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Easy Does It Wood Sole Slide Sandals
The kind of sandals you grab without thinking—and somehow they still pull the look together. Clean, grounded, and quietly cool, this wood-sole slide is made for slow mornings, long walks, and outfits that don’t try too hard.
Fit & Features
- Square toe silhouette
- Faux suede upper strap
- Wood sole with low block heel
- Stud detailing along the sole edge
- Cushioned footbed for everyday wear
- Runs true to size
Style Number/Barcode: 07404-000060
Category Name: Vacation Looks
Price: $12.97 $20.90
On Sale: Yes
Availability: In Stock
Available Color: TAN, WHITE
Available Size: 5, 5.5, 6, 6.5
Product Badge:- Sale
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Daytime Vibe Floral Eyelet Strapless Midi Dress
Currently planning your next cute daytime moment. This floral eyelet strapless midi dress hugs up top with a smocked fit, then flows out for that easy, throw-on-and-go vibe—perfect for brunch, beach days, or last-minute plans.
Fit & Features
- Woven floral eyelet fabric
- Strapless straight-across neckline
- Fitted smocked bodice
- Midi-length flowy A-line silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05102-000498
Category Name: Vacation Looks
Price: $31.97 $69.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: XS
Product Badge:- Sale
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Cutest Flirt Flutter Sleeve Skater Dress
You'll be the cutest flirt in this floral eyelet skater dress featuring short flutter sleeves, a drop waist design, and a tiered A-line silhouette. Style with espadrille wedges for weekend brunch!
Fit & Features
- Floral eyelet woven fabric, woven lining
- V-neckline, small keyhole cutout below the bust
- Short flutter sleeves, adjustable straps
- Back zipper closure, tie-back design
- Drop waist design
- Tiered mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05101-000898
Category Name: Vacation Looks
Price: $20.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: LIGHT, BLUE, WHITE-2
Available Size: M, L
Product Badge:- Sale
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Sculpted Shine Ring Set
Sleek, sculpted, and impossible to miss. This four-piece gold ring set mixes bold statement shapes with minimalist shine—perfect for stacking or wearing solo when you want to flex subtle luxury.
Fit & Features
- Four-piece ring set
- Polished finish
- Mix of sculptural and smooth band designs
Style Number/Barcode: 07004-000080
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: GOLD
Available Size: 8
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Play It Bold Drop Hoop Earrings
Statement hoops that do the talking. These drop hoop earrings bring that polished shine with a hint of edge—perfect for elevating your everyday lineup or finishing a last-minute outfit.
Fit & Features
- Drop hoop design
- Round metal stud
- Open metal and resin hoop
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000369
Category Name: Vacation Looks
Price: $9.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Soft Glam Floral Applique Mini Dress
Cute, but make it a little extra. This bodycon mini dress hugs just right with delicate floral applique details that feel made for dressy daytime plans and bridal soirees.
Fit & Features
- Smooth knit-lined stretchy fabric, floral applique
- Square neckline
- Adjustable spaghetti straps
- Side ruched seam
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001080
Category Name: Vacation Looks
Price: $19.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: XS, L
Product Badge:- Sale
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Flirty Polish Lace V-Neck Mini Dress
This lace skater dress features a soft, fitted bodice with a floaty skirt silhouette that feels made for bridal events, graduations, and every dressed-up occasion!
Fit & Features
- Lace fabric, lined
- V-neckline
- Adjustable spaghetti straps
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001134
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: WHITE
Available Size: S, M
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Softly Subtle Leaf Chain Necklace
This delicate lariat necklace drapes just right with dainty leaf details that catch the light and adds the perfect complement to your look.
Fit & Features
- Layered delicate chain design
- Leaf charm accents
- Lariat silhouette
- Lobster clasp closure
Style Number/Barcode: 07002-000437
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Stack The Attitude Five-Pack Ring Set
More rings, more attitude—because one is never enough. This five-pack ring set mixes asymmetric designs so you can stack, layer, or wear solo depending on the mood.
Fit & Features
- Five-pack ring set
- Multiple asymmetric designs
Style Number/Barcode: 07004-000127
Category Name: Vacation Looks
Price: $15.90
Availability: In Stock
Available Color: GOLD
Available Size: 8
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Perfectly Styled Pearl Charm Layered Necklace
Tiny detail, instant outfit upgrade. This pearl charm layered necklace mixes a sleek herringbone chain with a dainty textured chain for that perfectly styled finish.
Fit & Features
- Two-row layered design
- Herringbone chain
- Dainty textured chain, faux pearl charm
- Lobster clasp closure with extender
Style Number/Barcode: 07002-000475
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival
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Next Layer Seamless V-Neck Bodysuit
The base layer that does the most. This seamless bodysuit smooths, sculpts, and offers a sleek silhouette made to be worn under everything or styled on its own.
Fit & Features
- Seamless knit stretchy fabric
- Bonded V-neckline
- Adjustable spaghetti straps
- Form-hugging smooth fit
- Thong bottom
- Dual snap-button closures
- Runs true to size
Style Number/Barcode: 07102-000058
Category Name: Vacation Looks
Price: $18.90
Availability: In Stock
Available Color: WHITE
Available Size: L
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Soft Sculpt A-Line Mini Tube Dress
Fit & Features
- Smooth knit fabric with knit lining, high stretch
- Strapless straight-across neckline
- Open cross-back strappy design
- Ruched detailing
- Mini-length hem
- Fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05103-000872
Category Name: Vacation Looks
Price: $38.90
Availability: In Stock
Available Color: WHITE
Available Size: S, L
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Stack It Up Five-Pack Ring Set
Caught in your accessorizing era. This five-pack ring set brings all the chunky designs and stone embellishments you need to switch up your vibe from casual coffee runs to last-minute plans.
Fit & Features
- Five-pack ring set
- Multiple chunky designs
- Stone embellishments
Style Number/Barcode: 07004-000125
Category Name: Vacation Looks
Price: $16.90
Availability: In Stock
Available Color: PINK
Available Size: 7, 8
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Found The Gem Chain Necklace
This lariat chain necklace features an elongated lariat silhouette and eye-catching stone detail that layers beautifully or stands confidently on its own.
Fit & Features
- Colored stone accents
- Lariat silhouette
- Chain design
- Lobster clasp closure
Style Number/Barcode: 07002-000489
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: NS
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Keepsake Glow Five-Piece Ring Set
The kind of ring stack that looks like it has a story behind every piece. This five-piece ring set pairs marbled stone details, textured bands, and a statement teardrop centerpiece for an effortlessly collected look.
Fit & Features
- Five-piece ring set
- Colored marbled stone details
- Textured bands
- Statement designs
- Polished finish
Style Number/Barcode: 07004-000130
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: 7, 8
Product Badge:- New Arrival
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Talk Of The Town Mesh Mini Dress
The kind of dress that makes mirror selfies mandatory. This off shoulder mini dress drapes in all the right places with a blouson fit and flowing sash detail that's polished and flirtatious.
Fit & Features
- Mesh fabric lined with stretchy knit
- One-shoulder neckline
- Attached sash accent
- Blouson relaxed bodice
- Fitted mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000943
Category Name: Vacation Looks
Price: $38.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, L
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Dress Code Drama Stone Chain Necklace
The outfit needed a little extra, so naturally, this showed up. A chunky chain necklace with asymmetric stone accents that gives strapless looks, sleek knits, and going-out 'fits a sharper finish.
Fit & Features
- Chunky chain-link design
- Asymmetric center stone accents
- Lobster clasp closure with extender
Style Number/Barcode: 07002-000514
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival
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Desert After Dark Fringe Shoulder Bag
Add western drama with this faux suede shoulder bag that brings movement and attitude to every outfit. The adjustable belted strap with stud accents and fringe tassel charms makes it perfect for festivals, concerts, or adding flair to everyday looks.
Fit & Features
- Faux suede material
- Adjustable western-inspired belted shoulder strap, stud accents
- Fringe tassel charms
- Top zipper closure
- Spacious lined interior with an open pocket
Style Number/Barcode: 07203-000197
Category Name: Vacation Looks
Price: $30.90
Availability: In Stock
Available Color: CAMEL
Available Size: NS
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Coastal Daydream Maxi Skirt
Floaty, effortless, and made for sunny vacations and weekend plans. This tiered maxi skirt brings an easy beach to brunch feel with a breezy silhouette that moves with you.
Fit & Features
- Airy woven fabric, short woven lining
- High-rise stretchy smocked tie waist
- Flowy tiered ruffled silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06301-000015
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: WHITE
Available Size: L
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Caught Looking Rectangle Sunglasses
Serving quiet luxury with a little attitude. These retro-inspired rectangle sunglasses are the kind you throw on when the outfit needs one last detail that says “yeah, I planned this.”
Fit & Features
- Lightweight plastic frame construction
- Structured rectangle silhouette
- Tinted lenses with a sleek finish
- Thin side arms with a vintage-inspired feel
- 100% UV protection
Style Number/Barcode: 07008-000227
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: TORTOISE
Available Size: NS
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Coffee First Oval Sunglasses
The sunglasses you'll keep reaching for. These sleek oval sunglasses bring an effortless, wear-with-everything vibe that works for coffee runs, weekend plans, and everything in between.
Fit & Features
- Oval shaped silhouette
- Tinted lenses
- 100% UV protection
- Metal arms with plastic trim
Style Number/Barcode: 07008-000167
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
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Late Checkout Cat Eye Sunglasses
Vacation mode mentally, even if you’re just grabbing coffee. These cat eye sunglasses bring a sleek throwback vibe that instantly makes denim, basics, and messy buns feel styled.
Fit & Features
- Lightweight plastic frame
- Cat eye silhouette
- Tinted lenses
- Slim arms with polished hardware accents
Style Number/Barcode: 07008-000238
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BROWN
Available Size: NS