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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Goes With Everything Thong Sandals
Simple, sleek, and always in rotation. These thong sandals keep it minimal with a clean silhouette that goes with everything, making them your easy grab for errands, weekend plans, and last-minute outfit saves!
Fit & Features
- Square toe design
- Minimal thong toe strap
- Cushioned footbed
- Flat sole
- Luxe fit cushioned sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-000047
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: BLACK
Available Size: 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Pretty Petals Flower Hair Claw Clip Set
Cute hair day incoming. This flower hair claw clip set makes styling feel effortless with playful petal designs that add a soft, fun finish to any look.
Fit & Features
- Three-pack hair claw clip set
- Varying-sized flower designs
Style Number/Barcode: 07006-000138
Category Name: Vacation Looks
Price: $5.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Styled And Booked Halter Top
This top is what you throw on when the plan is “look cute, no stress.” This paisley halter top drapes effortlessly with a tie front and flowy fit—perfect with denim when you want that styled but chill vibe.
Fit & Features
- Paisley print, woven fabric
- Halter neckline with tie front
- Open back with stretchy smocked panel
- Flowy flyaway crop silhouette
- Runs true to size
Style Number/Barcode: 06003-000278
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunkissed Siren Beaded Abstract Print Bikini Top
Soft glow, sun-kissed skin, and this bikini top doing all the talking. The abstract print and beaded details give you that effortlessly styled look that feels just as good lounging poolside as it does layered under denim. Style with the matching bikini bottoms.
Shop Matching Bottoms: Sunkissed Siren Beaded Abstract Print Bikini Bottoms
Fit & Features
- Knit fabric, high stretch
- Abstract print
- Triangle design, center turquoise-embellished oval-shaped accent
- Halter tie-back spaghetti straps, beaded accents
- Lower tie-back spaghetti straps
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 07104-000018
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: In Stock
Available Color: MULTI
Available Size: L
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Double Take Floral Chiffon Ruffle Maxi Dress
Cue the double takes. This floral chiffon maxi dress brings the drama with ruffles, cutouts, a flirty slit, and breezy movement that shows up beautifully everywhere from brunch plans to sunset parties.
Fit & Features
- Sheer chiffon fabric with full-length stretchy knit lining
- Sleeveless sweetheart neckline, no-slip strip, padded bust, knotted center
- Halter tie-back straps, stretchy smocked back
- Asymmetric side cutouts leading to an open lower back
- Ruffled design, high-cut front slit
- Maxi-length flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-000888
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bold Allure Abstract Animal Print Mini Skort
Not here to blend in—this one sets the tone. This abstract animal print mini skort hugs just right with a mid-rise waist, tiered ruffled design, and airy mesh feel that keeps things bold but effortless. Style with the matching halter top.
Shop Matching Top: Bold Allure Abstract Animal Print Halter Top
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Abstract animal print
- Mid-rise waist
- Tiered ruffled design, mini-length overlay, A-line fit
- Tie detail, short side slit
- Hidden fitted knit shorts
- Runs true to size
Style Number/Barcode: 06503-000224
Category Name: Vacation Looks
Price: $29.90
Availability: Out of Stock
Product Badge:- Ships Free
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City Walk Tortoise Oversized Sunglasses
Put these on, and suddenly your outfit feels more put-together. These oversized tortoise sunglasses bring that effortless polish with a bold frame that works from coffee runs to weekend plans.
Fit & Features
- Tinted lenses
- Oversized sunglasses silhouette
- Square shape with rounded edges
- Tortoise pattern
Style Number/Barcode: 07008-000168
Category Name: Vacation Looks
Price: $4.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Love The Drama Oversized Sunglasses
A little mysterious, a little extra—in the best way. These oversized sunglasses give instant polish with a bold shape that pulls your whole look together, even on your most off-duty days.
Fit & Features
- Tinted lenses
- Oversized sunglasses silhouette
- Rounded square shape
Style Number/Barcode: 07008-000174
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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It Girl Energy Rimless Shield Sunglasses
These are giving instant main character. The rimless shield design with that warm tinted lens hits different—sleek, bold, and a little futuristic. Perfect for when your outfit needs that extra edge without trying too hard.
Fit & Features
- Rimless shield sunglasses design
- Tinted lenses with warm tone finish
- Rubber nose supports
- Lightweight metal frame construction
Style Number/Barcode: 07008-000178
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pretty Little Plans Eyelet Ruffle Romper
Cute plans call for something this good. This eyelet romper features delicate straps, a softly ruched bodice, and a flirty tiered skirt that gives you the look of a mini dress with the comfort of built-in shorts.
Fit & Features
- Eyelet fabric
- V-neckline with adjustable spaghetti straps
- Ruched fitted bodice
- Tiered flowy skirt with built-in shorts
- Runs true to size
Style Number/Barcode: 06503-000248
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Babe Floral Skater Mini Dress
This dress feels like a soft summer day. The airy chiffon, delicate floral print, and flirty tiered skirt give it that effortless romantic vibe. Finished with a lace-up back for a little extra charm at parties, brunch, or any dressy occasion.
Fit & Features
- Floral print chiffon-lined fabric
- Sweetheart neckline, twist bust
- Spaghetti straps that shape the lace-up back
- Skater silhouette
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000866
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ocean Daydream Seashell Mini Dress
Catch flights or just compliments in this mini dres that hugs just right with delicate shell details and a breezy open back made for sunny getaways and golden hour dinners.
Fit & Features
- Crochet knit-lined fabric with seashell embellishments
- V-neckline
- Spaghetti straps shape the lace-up back design
- Bodycon fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000536
Category Name: Vacation Looks
Price: $24.97 $52.90
On Sale: Yes
Availability: In Stock
Available Color: NATURAL
Available Size: M
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Easy Elegance A-Line Maxi Dress
Chic, minimal, and made for any moment. This strapless maxi dress keeps it effortless with a fitted bodice and flowy skirt that moves with you—perfect for everything from beach strolls to brunch dates.
Fit & Features
- Smooth knit stretch fabric
- Strapless tube neckline
- Fitted bodice
- Side pockets
- A-line silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000281
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beachside Charm Starfish Sandals
These faux pearl starfish strap flat sandals bring playful coastal charm with a sleek square toe that keeps every warm-weather look feeling effortlessly styled.
Fit & Features
- Square toe
- Faux pearl embellished starfish strap
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-000075
Category Name: Vacation Looks
Price: $9.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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No Questions Asked Mini Dress
This one doesn’t wait around. Command the room in this bodycon mini dress, offering a show of skin and a trendy hardware detail that pulls the look together. Pair with heels for a night out.
Fit & Features
- Texture knit fabric
- Plunge cutout neckline, hardware insert
- Adjustable spaghetti straps
- Cutout back
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 06005-000309
Category Name: Vacation Looks
Price: $15.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Petal Drip Plunge Maxi Dress
Soft glam, but make it unforgettable. This plunging halter maxi dress features a flowy cowl neckline and statement floral detail for your next event or sunset dinner moment.
Fit & Features
- Soft floral print, knit fabric
- Cowl halter neckline with flower inset
- Strappy tie-back
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-000840
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Weekend Escape Straw Cowboy Hat
Easy, effortless, and made for sun-soaked days. This woven straw cowboy hat features a breezy open weave and a braided tie with fringe detail for that laid-back western vibe that goes from beach to festival without missing a beat.
Fit & Features
- Straw material
- Structured cowboy hat silhouette
- Open weave design
- Braided tie detail with fringe ends
- Curved wide brim
- Adjustable inner strings for a snug fit
Style Number/Barcode: 07302-000311
Category Name: Vacation Looks
Price: $12.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Seaside Rodeo Shell Cowboy Hat
Coastal cowgirl is calling. This woven straw cowboy hat features a shell-trim band with subtle rope detail, giving beachy energy with a western twist—perfect for vacations, festivals, or sunny day styling.
Fit & Features
- Seashell trimmed band with string tie
- Wide curved brim
- Classic cowboy hat silhouette
- Straw material
Style Number/Barcode: 07302-000313
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunlit Fringe Straw Cowboy Hat
Golden hour, all day long. This straw cowboy hat features an airy woven design with frayed edges and a relaxed tie detail for that effortlessly undone, beach-to-desert vibe.
Fit & Features
- Structured cowboy hat silhouette
- Wide curved brim, frayed edge trim
- Adjustable chin cord with slider bead
- Open weave design
Style Number/Barcode: 07302-000312
Category Name: Vacation Looks
Price: $25.90
Availability: In Stock
Available Color: IVORY
Available Size: NS
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Cool Contrast Bangle Bracelet Set
Texture play that hits different. This bangle bracelet set combines sleek finishes with statement accents for a stacked look that feels effortless yet styled.
Fit & Features
- Two-piece bangle bracelet set
- Smooth and textured finishes
- Stud embellished
- Various styles and designs
Style Number/Barcode: 07003-000226
Category Name: Vacation Looks
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortlessly That Pair Oval Sunglasses
The kind of sunglasses you slip on heading out the door—and suddenly it all makes sense. The sleek oval shape and warm tone keep things minimal but still feel intentional, like you planned the look even if you didn’t.
Fit & Features
- Oval frame silhouette
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000121
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
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Roxanna Floral Print Strapless Mermaid Dress
Special Occasion
Made for that slow-turn moment, the Roxanna floral printed knit mermaid dress hugs in all the right places before flowing into a sleek, sculpted finish. The strapless neckline and ring back detail add just enough intrigue—perfect for when you want to look polished but still unforgettable.
Fit & Features
- Lined stretch knit fabrication
- Sleeveless square neckline, padded bra cups
- Large floral print pattern
- Open back with ring detail accent
- Floor-length mermaid silhouette
- Hidden side zipper closure
- Runs true to size
Where to Wear:
Prom, birthday celebrations, dressed-up dinners, and formal parties.
Style Number/Barcode: 05002-000877
Category Name: Vacation Looks
Price: $19.97 $79.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Card Energy Abstract Cutout Halter Mini Dress
This one’s for the plans that start late and go later. An abstract print cutout halter mini dress that sculpts your shape and brings just enough edge for nights out, rooftop hangs, and everything after.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Abstract print
- Sleeveless V-neckline with knotted detail at the bust
- Halter tie-back spaghetti straps
- Keyhole cutout, dual waist cutouts leading to an open back, lower tie-back spaghetti straps
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-000925
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Sheer mesh fabric with knit lining, high stretch
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Unforgettable In Floral Cutout Maxi Dress
This floral maxi dress was made for those nights that turn into memories. The halter neckline and front cutout bring the heat, while the flowy silhouette and thigh-high slit keep it effortlessly pretty.
Fit & Features
- Tropical floral print, knit-lined fabric
- Halter neckline with tie
- Open back
- Cutout bodice
- High front slit
- Form-hugging maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05101-000729
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free