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 Card Animal Print Halter Top
Shop Matching Bottoms: Wild Card Animal Print Maxi Skirt
Fit & Features
- Knit fabric, moderate stretch
- Abstract animal print
- Sleeveless deep sweetheart neckline
- Dual spaghetti straps, tie-back halter straps, adjustable straps
- Boning design
- Mid-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000664
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Caroline Lace Long Sleeve Formal Dress
Special Occasion
Dressed-up plans get a softer kind of drama with this lace look. The Caroline lace formal dress pairs ruffle trim, sheer bell sleeves, and a slim, floor-length silhouette for a romantic, movement-rich finish. The front slit and side cutouts bring just enough flair to the occasion.
Fit & Features
- Lined lace fabric
- V-neckline
- Long sheer bell sleeves
- Ruffle trim, side cutouts
- Front slit, curve-hugging silhouette
- Long-length hem
- Runs true to size
Where to Wear:
Destination weddings, bridal celebrations, honeymoons, vacations, resort getaways, cruises, yacht parties, birthday dinners, cocktail soirees, dressy celebrations
Style Number/Barcode: 05002-001577
Category Name: Vacation Looks
Price: $59.90
Availability: In Stock
Available Color: NATURAL, BLACK
Available Size: XS, S, M, L, XL
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After Hours Bloom Halter Maxi Dress
Dinner plans just got dangerously well dressed. This halter maxi dress hugs through the hips with sleek ruching, a statement floral accent, and a high slit made for entrances and exit shots.
Fit & Features
- Smooth stretch knit fabric
- Plunging V-neckline with halter straps
- Open back with adjustable tie closure
- Ruched hip with floral applique
- High side slit
- Maxi length silhouette
- Runs true to size
Style Number/Barcode: 05102-000822
Category Name: Vacation Looks
Price: $52.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Untamed Animal Print Halter Maxi Dress
Mixed animal print brings bold impact with a strappy open back. The plunging neckline and front slit add movement and shape, making this maxi dress ready for dinner dates, parties, and standout vacation looks.
Fit & Features
- Mixed animal print, lined chiffon fabric
- Plunging halter neckline
- Adjustable spaghetti straps
- Open back with adjustable straps, lower zipper and hook-eye closure
- Front high slit detail
- Flowy A-line floor-length maxi silhouette
- Runs true to size
Style Number/Barcode: 05103-001046
Category Name: Vacation Looks
Price: $31.97 $69.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: XS, S
Product Badge:- Sale
- Mixed animal print, lined chiffon fabric
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Penny Crochet Mermaid Formal Dress
Special Occasion
The crochet texture gives this formal dress its handcrafted, standout feel. This crochet mermaid formal dress pairs floral openwork panels with beaded multi-strap detail and a floor-length silhouette for a dimensional finish. The fitted mermaid shape keeps the look sleek from neckline to hem.
Fit & Features
- Floral openwork crochet fabric, partial mesh lining
- Halter V-neckline with tie straps
- Side zipper and hook-eye closure
- Beaded multi-strap detail
- Fitted mermaid silhouette
- Floor-length hem
- Runs true to size
Where to Wear:
Bridal celebrations, bachelorettes, vacations, honeymoons, destination celebrations, birthday dinners, resort getaways, cruises, brunch celebrations, summer date nights
Style Number/Barcode: 05002-001733
Category Name: Vacation Looks
Price: $89.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- Ships Free
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Bloom With It Two-Pack Hair Clips
For the hair days that need a little extra pretty. This two-pack of floral hair clips brings rhinestone sparkle, sculpted petal details, and an easy clip-on design for styling up half-up looks, loose waves, and last-minute plans.
Fit & Features
- Two-pack hair clip set
- Floral silhouette
- Rhinestone-embellished
- Clip-on closure
- Sculpted detailing
Style Number/Barcode: 07006-000175
Category Name: Vacation Looks
Price: $11.90
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Orchid Stud Earrings
A little unexpected, a lot unforgettable. These sculptural flower stud earrings pair textured petals with a metallic center for an organic statement that feels equal parts vintage treasure and modern art.
Fit & Features
- Sculptural flower stud earrings
- Textured petal design
- Contrasting metallic center detail
- Statement silhouette
- Post back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000473
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: NS
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Wild Charm Tooth Pendant Necklace
A little untamed, a lot of payoff. This pendant necklace brings a chunky chain and bold tooth charm that instantly sharpens up your favorite looks.
Fit & Features
- Chunky chain design
- Statement tooth pendant
- Polished metal finish
- Lobster clasp closure
Style Number/Barcode: 07002-000533
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- Sale
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Low Key Allure Polka Dot Halter Top
This is the top that does the talking when you turn around. A deep plunge up front and an open back moment make it equal parts bold and effortless, perfect for brunch dates or any chic plans!
Fit & Features
- Polka dot print woven fabric
- Halter neckline with deep V plunge
- Adjustable tie-back halter strap
- Open back with tie closure at mid-back
- Front cutout detail at bodice
- Flowy flyaway hem
- Runs true to size
Style Number/Barcode: 06003-000260
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BLACK, NAVY
Available Size: XS, S, M, L
Product Badge:- Back In Stock
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Charmed In Bloom Shoulder Bag
Soft details, but it still makes an entrance. This flower faux pearl asymmetrical shoulder bag brings a romantic edge with sculpted petals and a polished finish that feels occasion-ready.
Fit & Features
- Adjustable shoulder strap
- Asymmetrical mini silhouette
- Flower insets with faux pearl insets
- Top zipper closure
- Spacious interior
- Pebbled faux leather material
Style Number/Barcode: 07203-000139
Category Name: Vacation Looks
Price: $13.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Little Details Floral Print Skater Dress
Serving flirty little details from every angle. This floral print skater dress hugs in all the right places with a smocked fit and tiered ruffle skirt made for brunch dates, birthdays, and last-minute plans.
Fit & Features
- Lace fabric with lining
- Dainty floral print
- Sleeveless V-neckline, ruched bust, adjustable spaghetti straps
- Stretchy smocked waist, V-shaped drop waist design
- Tiered ruffled design
- Mini-length skater silhouette, sheer lace hem
- Runs true to size
Style Number/Barcode: 05101-001069
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty Plans Eyelet Tube Dress
Serving soft and sweet with a little flirt. This eyelet tube dress features a smocked waist and tiered skater skirt that feels light, playful, and perfect for brunch dates, showers, or sunny weekend plans.
Fit & Features
- Eyelet woven fabric lined with knit
- Strapless neckline
- Stretchy smocked fitted bodice
- Ruffled layered mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000858
Category Name: Vacation Looks
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Forever On Trend High Rise Ponte Capri Pants
Slip into these classic and chic ponte capri pants for effortless style! Channel a 90s vibe in these pants featuring a flattering high-rise waist, form-hugging fit, and flirty side slit accents along the hem. Complete the look in a basic tee and sandals!
Fit & Features
- Ponte knit fabric, minimal stretch
- High-rise waist
- Form-hugging fit
- Side slit accents
- Runs true to size
Style Number/Barcode: 06502-2533
Category Name: Vacation Looks
Price: $28.90
Availability: In Stock
Available Color: BLACK, BROWN, PLUM
Available Size: XS, S, M, L
Product Badge:- Back In Stock
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Flirty Fit Lace Ruffle Romper
The one that instantly upgrades whatever’s on your calendar. A lace cutout ruffle romper with a flirty fit that’s made for parties, birthdays, and last-minute invites you’re definitely saying yes to.
Fit & Features
- Sheer lace fabric with knit lining, moderate stretch
- Sleeveless plunging V-neckline, bar strap accent
- Halter tie-back spaghetti straps
- Open back, lower tie-back spaghetti straps
- Drop waist
- Tiered ruffled mini-length overlay, skater silhouette, hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06503-000252
Category Name: Vacation Looks
Price: $46.90
Availability: In Stock
Available Color: OFF, WHITE
Available Size: S, M, L
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Maria Open Back A-Line Formal Dress
Special Occasion
Effortless movement meets understated drama in The Maria formal dress, a textured jersey gown designed to turn every step into a statement. The plunge cowl halter neckline, open back design, and high side slit bring modern allure to the flowing A-line floor-length silhouette.
Fit & Features
- Textured jersey knit fabric, smooth knit lining, high stretch
- Plunge cowl halter neckline, tie straps
- Open back design
- High side slit
- A-line floor-length silhouette
- Runs true to size
Where to Wear:
Weddings, rehearsal dinners, engagement photoshoots, bridal celebrations, formal birthday events, honeymoons, vacations, resort getaways, yacht parties, cruises, date nights, anniversaries
Style Number/Barcode: 05002-001687
Category Name: Vacation Looks
Price: $79.90
Availability: In Stock
Available Color: WHITE, BROWN
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free
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On My Way Scarf Shoulder Bag
The bag that pulls the whole outfit together without even trying. With its structured shape, sleek top handle, and scarf detail, this shoulder bag was made for coffee runs, dinners, and everyday styling.
Fit & Features
- Top handles with snap-button strap
- Floral print attached scarf bow tie
- Top zipper closure
- Lined spacious interior, zipper pocket
- Pebbled faux leather material
Style Number/Barcode: 07203-000158
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortlessly Flirty Halter Skater Romper
Effortless outfit, maximum compliments. This halter skater romper brings the flirty vibes with a plunging neckline, twirl-worthy skirt overlay, and hidden shorts that keep up with every RSVP on your calendar.
Fit & Features
- Knit fabric, high stretch
- Sleeveless plunging V-neckline
- Halter strap, open back
- Fitted high waist
- Mini-length overlay, skater silhouette
- Hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06503-000270
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: OFF, WHITE
Available Size: XS, S, M, L
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Plans Before Sunset Striped Top
Looks like vacation plans, even if you’re just headed to lunch. This striped halter top brings a flirty fit and open back detail that elevates denim jeans and sandals.
Fit & Features
- Woven textured fabric, striped pattern, sewn-in knit lining
- Plunge halter neckline, bar accent
- Open front design
- Open back
- Mid-length hem
- Runs true to size
Style Number/Barcode: 06003-000333
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Caught Feelings Crochet Flyaway Top
Serving vacation crush energy without even trying. This crochet flyaway top has a breezy fit and peekaboo detail that makes denim days, beach plans, and rooftop nights feel instantly more styled.
Fit & Features
- Unlined crochet knit fabrication
- Sleeveless v-neckline
- Adjustable shoulder straps
- Tie-front accent
- Flyaway hem
- Runs true to size
Style Number/Barcode: 06005-000322
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty Persuasive Lace Corset Top
The kind of top that suddenly has your calendar looking booked. With a plunging V-neck, floral lace pattern corset fit, and lace-up back detail, this top was made for weekend plans and compliments from strangers.
Fit & Features
- Floral lace knit fabric, partial lining
- Plunge V-neckline
- Hidden front hook and eye fasteners
- Lace-up back
- Fitted corset-inspired silhouette
- Crop hem
- Runs true to size
Style Number/Barcode: 06001-000551
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
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Bead On It Halter Top
This halter crop top brings a sleek, fitted shape, beaded strap accents, and an open tie back made for concerts, vacations, and weekend plans.
Fit & Features
- Smooth ponte knit stretchy fabric
- Scoop halter neckline, beaded straps, tie
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000571
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Sheer Shimmer Off-The-Shoulder Poncho
Sheer shimmer, zero effort—this off-the-shoulder poncho is your go-to when your outfit needs a quick glow-up. The cropped, flowy fit gives just enough drama for plans that came up five minutes ago.
Fit & Features
- Lurex knit fabric, moderate stretch
- Asymmetric off-the-shoulder neckline
- Cropped silhouette
- Flowy fit
- Runs true to size
Style Number/Barcode: 06005-000380
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: BLACK, NATURAL
Available Size: XS/S, M/L
Product Badge:- Back In Stock
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Coffee Date Lace Trim Crop Top
Casual, but you still thought it through. This crop top brings a flattering fit with lace trim neckline and a low-cut back that makes every outfit feel a little more styled.
Fit & Features
- Knit stretchy fabric, various patterns
- Lace trim V-neckline
- Short sleeves
- Lace trim low-cut back
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06002-000585
Category Name: Vacation Looks
Price: $27.90
Availability: In Stock
Available Color: BLACK, YELLOW, BROWN
Available Size: S, M, L
Product Badge:- Back In Stock
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Sweet On Plans Polka Dot Mini Dress
Caught mid-stroll and looking sweet in this polka dot dress. This dress hugs just right with a form-hugging fit and a flirty ruffle hem made for daytime plans.
Fit & Features
- Polka dot print, knit, stretchy fabric
- One-shoulder neckline
- Form-hugging ruched fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000710
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: PINK
Available Size: L
Product Badge:- Sale