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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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: $42.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S
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Golden Rush Metallic Cowl Neck Top
Shimmer that hits different. This abstract print metallic cowl neck top drapes just right with a body-hugging fit that moves with you from golden hour drinks to after-dark plans. Style with the matching maxi skirt.
Shop Matching Bottoms: Golden Rush Metallic Ruffle Maxi Skirt
Fit & Features
- Foiled metallic knit fabric, abstract print, high stretch
- Sleeveless cowl neckline
- Spaghetti straps
- Metal O-ring back accents
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000322
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: METALLIC
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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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: $21.90
Availability: In Stock
Available Color: GOLD
Available Size: 5.5, 6, 6.5, 7, 7.5, 10
Product Badge:- Best Seller
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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: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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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: $52.90
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
- Adjustable inner strings for a snug fit
Style Number/Barcode: 07302-000312
Category Name: Vacation Looks
Price: $25.90
Availability: Out of Stock
Product Badge:- Ships Free
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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: $13.90
Availability: Out of Stock
Product Badge:- Ships Free
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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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Sunset Stunner Mesh Strapless Midi Dress
Hot plans, zero overthinking—this dress just gets it. A sleek strapless mesh midi that hugs in all the right places and shows up ready for every RSVP on your calendar.
Fit & Features
Style Number/Barcode: 05102-000611
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
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Hailey Strapless Mermaid Formal Dress
Special Occasion
The Hailey mesh mermaid gown hugs in all the right places with a softly sculpted, second-skin feel. The strapless neckline and ruched detailing create a fluid, flattering shape, while the sheer illusion bodice adds a modern, barely-there edge.
Fit & Features
- Knit fabric, partial lining
- Strapless neckline, twist bust
- Sheer mesh bodice
- Mermaid silhouette with drape accent
- Floor-length hem
- Runs true to size
Where to Wear:
Prom, weddings, formal occasions, vacations, resorts, honeymoons, birthday dinners, engagement parties, bridal celebrations
Style Number/Barcode: 05002-001201
Category Name: Vacation Looks
Price: $69.90
Availability: In Stock
Available Color: YELLOW
Available Size: XXS, XS, S, M, L
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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: $79.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L, XL
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: $38.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
- 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: $49.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Barely Trying Open Back Midi Dress
This is that effortless dress you reach for when you want to feel cute and put together. The open back adds a soft, unexpected moment, while the ribbed fit keeps everything sleek and flattering.
Fit & Features
- Rib knit stretchy fabric
- Scoop neckline
- Spaghetti straps
- Open back
- Side slit
- Form-hugging, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000553
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
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Soft Focus Muse Floral Lace-Up Maxi Tube Dress
Caught feelings for this one instantly. This floral maxi tube dress hugs just right with a lace-up back that brings a little extra drama for nights out or dressed-up day plans.
Fit & Features
- Smooth stretch knit fabrication
- Sleeveless ruched sweetheart neckline
- Large floral pattern
- Lace-up back design
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-001120
Category Name: Vacation Looks
Price: $54.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Spritz And Plans Strapless Mini Dress
This dress has "take me on vacay" written all over it! The playful print and easy strapless fit keep it light, while the flowy mini hem makes it perfect for enjoying a sunny day on your next getaway.
Fit & Features
- Garden fruit and veggie print, woven fabric, stretchy knit lining
- Strapless neckline, stretchy smocked bodice
- Fit and flare silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000617
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Wild Plans Animal Print Cutout Maxi Dress
Not a subtle entrance kind of dress. This animal print maxi dress hugs your curves with a flirty open back and lace-up detail that’s made for vacations, sunset dinners, and cocktail bars with the girls.
Fit & Features
- Animal print, mesh fabric lined with knit
- Sweetheart neckline, twist bust
- Spaghetti straps
- Strappy open back
- Cutout bodice
- Curve-hugging, maxi hem
- Runs true to size
Style Number/Barcode: 05103-000611
Category Name: Vacation Looks
Price: $46.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
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Garden After Dark Plunge Halter Maxi Dress
This is the kind of entrance that doesn’t need explaining. With a plunging neckline, open back, and butterfly chain detail, this floral maxi dress is equal parts romance and edge—made for date nights and rooftop hotel bars.
Fit & Features
- Floral abstract print, mesh-lined fabric
- Plunge halter V-neckline with tie closure
- Butterfly hardware with draped chain accent
- Open back with adjustable strappy detail
- Form-hugging floor-length hem
- Runs true to size
Style Number/Barcode: 05103-000568
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L, XL
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Maia Floral Print Sequin Mermaid Dress
Special Occasion
Cue the compliments in the Maia sequin mermaid dress that shimmers with a dreamy floral print that feels straight out of a getaway moment. The sculpted silhouette hugs in all the right places, while delicate straps and an open lace-up back keep it effortlessly alluring.
Fit & Features
- Knit fabric with large floral print, full-length knit lining, moderate stretch
- All-over clear sequin embroidery
- Sleeveless V-neckline, padded bust
- Spaghetti straps
- Open lace-up strappy back with tie closure, lower back zipper with hook-eye closure
- Floor-length mermaid silhouette
- Runs true to size
Where to Wear:
Prom, birthday celebrations, vacations, honeymoons, resorts, and summer parties.
Style Number/Barcode: 05002-000614
Category Name: Vacation Looks
Price: $119.90
Availability: In Stock
Available Color: PINK
Available Size: XXS, XS, S, M, L
Product Badge:- Ships Free
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Sultry Vibe Paisley Print Bodycon Maxi Dress
The kind of dress that does all the talking the second you walk in. This paisley print bodycon maxi dress skims your shape with a soft, sculpting stretch—perfect for sultry nights out.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Paisley print
- Sleeveless square neckline
- Adjustable spaghetti straps
- High-cut side slit
- Maxi-length hem, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000664
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Sunlit Muse Paillette Sequin Mini Cover-Up
Shimmer that catches the light and refuses to be subtle. This paillette sequin bikini cover-up features a side tie closure that keeps the fit adjustable for beach days, poolside lounging, or sunset photos. Style with the matching bikini top and bottoms.
Shop Matching Set: Sunlit Muse Paillette Sequin Bikini Top, Sunlit Muse Paillette Sequin Bikini Bottoms
Fit & Features
- Mesh fabric, smooth sewn-in knit lining, moderate stretch
- Paillette sequin embroidery
- Side tie closure
- Mini-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 07105-000037
Category Name: Vacation Looks
Price: $33.90
Availability: In Stock
Available Color: TAUPE
Available Size: S/M, L/XL
Product Badge:- Part of a Set
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Sparkly Rhinestone Thong Sandals
A little sparkle goes a long way—these metallic rhinestone thong sandals bring just enough shine to dress up your look.
Fit & Features
- Almond toe
- Rhinestone-embellished thong strap
- Flat sole
- Metallic material
- Traction bottom
Style Number/Barcode: 07404-000045
Category Name: Vacation Looks
Price: $16.90
Availability: In Stock
Available Color: GOLD
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10