We've sent you an email with a link to update your password.
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.
Get Eye-Catching Sandals For Women
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.
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.
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.
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.
Sweet Intentions Flower Strapless Mini Dress
Soft details, confident energy. This strapless mini dress pairs a sweetheart neckline with a subtle cutout and floral accent for a look that feels romantic but never too precious.
Fit & Features
Style Number/Barcode: 05102-000412
Category Name: Vacation Looks
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Rosé Nights Floral Halter Maxi Dress
Romantic without feeling try hard. This floral mesh maxi dress skims the body with a soft stretch fit, finished with delicate sparkle details that make it perfect for weddings, date nights, or dressed-up evenings that call for something extra.
Fit & Features
Style Number/Barcode: 05101-000730
Category Name: Vacation Looks
Price: $64.90
Availability: In Stock
Available Color: MAUVE
Available Size: XS, S, M, L, XL
Letina Metallic Knit Mermaid Formal Dress
Special Occasion
Designed for evenings that call for quiet confidence, The Letina glides with a fluid metallic knit that catches the light with every step. A plunge halter wired neckline and ruched mermaid silhouette create a sculpted, unforgettable presence that feels equal parts polished and alluring.
Style Number/Barcode: 05002-000808
Category Name: Vacation Looks
Price: $79.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: XS, S, M, L, XL
Eyes On You High Slit Maxi Skirt
Just enough to catch their attention. This high slit maxi skirt sculpts with soft stretch and statement hardware, giving effortless confidence from sunset plans to late nights.
Shop Matching Top: Eyes On You Cutout Tube Top
Fit & Features
Style Number/Barcode: 06501-000114
Category Name: Vacation Looks
Price: $36.90
Availability: Out of Stock
Polished Plans Pearlescent Metal Handle Clutch
Small bag, strong finish. This pearlescent clutch pulls everything together with a sleek metal handle that feels equal parts elevated and effortless—perfect for events, dinners, and dressy plans.
Fit & Features
Style Number/Barcode: 07204-000045
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: IVORY
Available Size: NS
Eyes On You Cutout Tube Top
Just enough to catch their attention. This cutout tube top sculpts with soft stretch and statement hardware, giving effortless confidence from sunset plans to late nights.
Shop Matching Bottoms: Eyes On You High Slit Maxi Skirt
Fit & Features
Style Number/Barcode: 06001-000420
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Clear Choice Jelly Thong Kitten Heels
Minimal, glossy, and ready to go wherever the plans land. These jelly thong kitten heels add just enough lift with an easy slip-on style, perfect for day plans or sunset cocktails by the beach!
Fit & Features
Style Number/Barcode: 07401-000568
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: PINK
Available Size: 6, 7, 8, 10, 5
Unforgettable Entrance Plunge Neck Maxi Dress
This maxi dress doesn’t blend in—it arrives. This plunging cowl neck maxi dress drapes smoothly through the body with a halter neckline that feels bold, polished, and intentionally striking. Pair with heels for date night, dressy celebrations, or a sultry vacation look.
Fit & Features
Style Number/Barcode: 05101-000736
Category Name: Vacation Looks
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Getaway Mood Tropical Floral Halter Maxi Dress
Lightweight, curve-loving, and made to move with you. The airy sheer mesh fabric and tropical floral print bring a bold edge that feels right for nights out and getaway moods.
Fit & Features
Style Number/Barcode: 05102-000464
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
Set The Tone Halter Ruffle Romper
This look sets the tone the second you walk in. With a plunging halter neckline and layered ruffles, this romper brings flirty movement, confident curves, and just enough drama for nights out.
Fit & Features
Style Number/Barcode: 06503-000216
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: NEON, PINK
Available Size: XS, S, M, L
Sunset Mood Tropical Floral Maxi Skirt
The skirt that belongs in your suitcase and your camera roll. Draped just right with a body-skimming fit, this tropical floral maxi skirt is made for warm nights, golden hours, and wherever the mood takes you. Style with the matching halter top.
Shop Matching Top: Sunset Mood Tropical Floral Halter Top
Fit & Features
Style Number/Barcode: 06501-000113
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
Sweet Bloom Flower Hair Clip Set
Sweet bloom, instant upgrade. This flower hair clip set pulls your look together in seconds—perfect for off-duty days, sunny errands, or a low-effort glow-up moment.
Fit & Features
Style Number/Barcode: 07006-000071
Category Name: Vacation Looks
Price: $11.90
Availability: Out of Stock
Pretty Plans Pending Floral Tube Mini Dress
Romantic from every angle, no overthinking required. This floral tube mini dress hugs smoothly and easy, making it the kind of dress you grab when the plan is cute but the vibe is confident.
Fit & Features
Style Number/Barcode: 05102-000456
Category Name: Vacation Looks
Price: $35.90
Availability: In Stock
Available Color: PINK
Available Size: S, M, L
Island Luxe Metallic Knit Poncho
Glow like the golden hour in this sheer metallic poncho that was made for sipping cocktails with a view. Lightweight and breezy, it’s the perfect topper for your bikini or a slinky resort night look.
Fit & Features
Style Number/Barcode: 06202-000086
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: GOLD, SILVER, BLACK
Available Size: XS/S, M/L
Sun Chaser Crochet Halter Top
Instant vacation mode, no ticket required. This crochet halter top features a plunging cowl neckline with a hoop detail that feels bold, effortless, and made for warm days that turn into golden-hour plans. Shop the matching bottoms.
Shop Matching Bottoms: Sun Chaser Crochet Shorts
Fit & Features
Style Number/Barcode: 06003-000264
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: RED
Available Size: XS, S, M, L
Effortlessly Bold Abstract Print Halter Mini Dress
Soft drama with a daring edge. This abstract print halter mini dress hugs where it counts and moves like it knows you’ve got plans—perfect for nights out, birthday 'fits, and anytime subtle just isn’t the goal.
Fit & Features
Style Number/Barcode: 05102-000326
Category Name: Vacation Looks
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Weekend Wandering Open Back Maxi Dress
Light, airy, and made for unhurried afternoons that turn into early evenings. This gauze maxi drapes effortlessly, skims the body just right, perfect for shower celebrations, vacation, or a brunch.
Fit & Features
Style Number/Barcode: 05102-000416
Category Name: Vacation Looks
Price: $56.90
Availability: In Stock
Available Color: PINK
Available Size: S, M, L
Sweet With Intent Lace Tiered Mini Dress
Soft, flirty, and perfectly styled without trying too hard. This lace mini dress features a knotted bust and a tiered skirt that feels light, feminine, and made for plans that turn into photos.
Fit & Features
Style Number/Barcode: 05101-000946
Category Name: Vacation Looks
Price: $52.90
Availability: Out of Stock
All Eyes On Me Floral Open Back Maxi Dress
This floral mesh maxi dress features a plunging cowl halter neckline and an open back that feels equal parts romantic and intentional—made for weddings, date nights, and birthday cocktails.
Fit & Features
Style Number/Barcode: 05101-000677
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: WINE
Available Size: XS, S, M, L, XL
Late Arrival Abstract Maxi Dress
Moody, sculpted, and impossible to ignore. This maxi dress hugs in all the right places with a plunging neckline and statement ring detail that feels made for vacations, sunset dinners, and GNOs!
Fit & Features
Style Number/Barcode: 05102-000348
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Effortless Bloom Floral Open Back Maxi Dress
Floaty, fitted, and impossible to ignore. This floral mesh maxi skims the body with a draped cowl neckline and an open tie-back design perfect for serving dreamy looks on vacations, sunset cocktails, and date nights.
Fit & Features
Style Number/Barcode: 05101-000845
Category Name: Vacation Looks
Price: $52.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L, XL
Chic Shine Stone Hoop Earrings
The kind of detail that pulls a look together. These stone hoop earrings bring a sleek, sculptural feel with faceted stones that catch the light and make even the simplest outfit feel intentional.
Fit & Features
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000329
Category Name: Vacation Looks
Price: $13.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Golden Hour Groove Crochet Halter Maxi Dress
Vacation energy, locked in. This striped texture crochet knit maxi dress features a plunge halter neckline with wooden hoop inserts and an open back that feels equal parts effortless and elevated. Pair with strappy sandals for your upcoming getaway.
Fit & Features
Style Number/Barcode: 05102-000461
Category Name: Vacation Looks
Price: $46.90
Availability: In Stock
Available Color: RED
Available Size: XS, S, M, L
Easy Statement Filigree Hoop Earrings
Intricate, airy, and instantly eye-catching. These filigree hoop earrings bring a vintage-inspired texture that elevates everyday looks and adds an effortless finish to dressed-up plans.
Fit & Features
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000297
Category Name: Vacation Looks
Price: $9.90
Availability: Out of Stock
