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.
Now Trending
STYLE SPOTLIGHT
Get Eye-Catching Sandals For Women
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.
-
Ring The Alarm Smocked Romper
You're just too hot to handle, set it off in this fiery romper! It features a vibrant red hue, an off the shoulder neckline, a smocked bodice, off the shoulder strap accents with tie details and wide leg shorts. Romper is composed of a lined lightweight textured woven fabric that offers a form hugging fit with a minimal stretch.Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 06403-1039
Category Name: Vacation Looks
Price: $4.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Flirt Alert Tie Waist Romper
Ring the alarm! This flirty romper is just what you need to get your playful message across. It features a wide V neckline, adjustable wide straps with an O ring detail at the back, a paper bag waist with a tie belt detail, and form hugging shorts. Romper includes a hidden back zipper. Romper is made from a soft, densely woven material with moderate stretch.Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 06403-0019
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sealed With Style Jumpsuit
Seal your look with style with this chic jumpsuit! It features a sleeveless bodice, a lined white hued top with adjustable spaghetti straps, a V neckline, and a side zipper and hook and eye closure connected to a pair of high rise paper bag pants with a tie front belt, slanted front pockets, pleated details, and a straight leg fit. The jumpsuit is composed of a woven fabric with no stretch.Model is 5'8" with a 33" bust, 24" waist and 33.5" hips. She is wearing a size small.
Style Number/Barcode: 06402-0016
Category Name: Vacation Looks
Price: $4.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Effortlessly Chic Paper Bag Romper
Make an effortlessly chic impression in this pretty coral romper! It features a white hued lined bodice, a V neckline and narrow adjustable straps. The coral hued paper bag shorts feature a cinching tie waist belt, side pockets and a wide leg rolled hem. Romper is composed of a lightweight woven fabric that offers a relaxed fit with a minimal stretch.Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06403-0000
Category Name: Vacation Looks
Price: $4.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Living In Linen Romper
Oh you know you, just living your best life in this linen romper! It features a sleeveless bodice, a wrap front creating a V neckline, adjustable spaghetti straps, an elastic banded waist, slanted side pockets, and relaxed fitting shorts with a cuffed hem. The rust hued romper is composed of a linen fabric with no stretch.Model is 5'8" with a 33" bust, 24" waist, and 35" hips. She is wearing a size small.
Style Number/Barcode: 06303-0870
Category Name: Vacation Looks
Price: $4.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Spring It On Flowy Shorts
Spring it on with these flirty floral flowy shorts! They feature a high rise elastic banded waist, slight pleated details, and a flowy fit. The black shorts are composed of a lightweight woven fabric with an adorable all over ditsy daisy print. Complete your spring ready look with the matching crop top!
Style Number/Barcode: 06303-0867
Category Name: Vacation Looks
Price: $26.90
Availability: Out of Stock
Product Badge:- Clearance
-
Set In Stripes Paperbag Shorts
Ready, set, go! You're all set to go in these light blue paperbag shorts! They feature a high rise waist, a tie front waist and wide leg opening. The all over white stripes create a fresh contrast for the dreamy light blue background. Shorts are composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Be sure to pick up the matching top to complete your look!Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06303-0864
Category Name: Vacation Looks
Price: $4.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Check 'Em Out Gingham Shorts
Check you out in these black gingham shorts, girl! You'll be ready for summer with a high waist, a button up front with zipper closure, and a slim fit. Shorts are composed of a stretchy knit fabric that offers a moderate stretch.Model is 5'7" with 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06303-0865
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Summer Chic Tie Front Romper
The season calls for super cute outfits! This easy romper features a plunging V neckline with a cut out and tie detail, short sleeves, and shorts. Gauze-like fabric offers a lightweight fit with no stretch. Includes back zipper closure.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06303-0000
Category Name: Vacation Looks
Price: $32.90
Availability: Out of Stock
Product Badge:- Clearance
-
Gives You Lemons Pajama Top
When life gives you this lemon print pajama top will make every lounge or sleep will look sweet! Pair with the matching pajama bottoms to complete the look.
Fit & Features
- Lemon print, stretchy knit fabric
- Short sleeves
- Crew neckline
- Fitted crop hem
- Runs true to size
Shop The Matching Pajama Shorts: Gives You Lemons Pajama Shorts
Style Number/Barcode: 07103-000016
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Bask In The Sun Romper
Bask in the sun with in this gorgeous eyelet detail romper! It features ruffle sleeves with ruffle detailing down the front, an open back with a tie back closure, a back zipper and hook and eye closure, slanted front pockets, and fitted shorts. The mustard yellow romper is composed of a sheer eyelet fabric with a full woven lining and offers no stretch.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06303-0030
Category Name: Vacation Looks
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Distressed Diva Bermuda Shorts
These shorts are diva-approved for your trendsetting looks! They feature a mid-rise fit, a single button with zipper closure, a five pocket with belt loop design, moderate distressed detailing throughout and a fab bermuda length. Shorts are composed of a denim fabric that offers a relaxed fit with a moderate stretch.
Style Number/Barcode: 06303-0014
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Bohemian Vibes High Waist Pants
Channel those carefree boho vibes in these cute pants! It features a mustard hue, a high rise waist and straight leg pants with a flared hem. The all over white hued bohemian stripes are all you need to brighten your look! Pants are composed of a gauze fabric that offers a relaxed fit with minimal stretch.Be sure to pick up the matching top to complete your look!Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06302-0583
Category Name: Vacation Looks
Price: $4.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Tropical Escape Sleeveless Jumpsuit
Transport yourself to an island paradise in this vacay-ready jumpsuit! It features a pretty pink hue, a sleeveless sweetheart neckline, a no slip strip, a small keyhole and wide leg pants. The all over palm leaf print features a green hue that perfectly complements the pink background. Jumpsuit is composed of a lightweight woven fabric that offers a form hugging fit with minimal stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06302-0021
Category Name: Vacation Looks
Price: $42.90
Availability: Out of Stock
Product Badge:- Clearance
-
Always A Savage Skinny Pants
These gray snake skinny pants are so savage, you'll never be average! They feature a high rise fit with a belted waist, a zipper and hook and bar front closure, two front and back pockets, a skinny fit, and an all over gray snake print with a contrasting white hue. The pants are composed of a denim fabric that offers moderate stretch.Model is 5'9" with a 32" bust, 23" waist, and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06302-0006
Category Name: Vacation Looks
Price: $30.00 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Such A Flirt Linen Mini Skirt
Girl, you'll be such a flirt in this lovely linen mini skirt! It features a white hue and a high rise waist paired with a short, A-line fit. Includes a knit lining. Complete your flirty look with the matching crop top!Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06301-0467
Category Name: Vacation Looks
Price: $10.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Vibrant Vacay Maxi Skirt
Make your vacay a vibrant one in this tropical printed maxi skirt! It features a high rise waist, an elastic banded back, a hidden side zipper and hook and eye closure, two thigh high side slits, and a flowy, relaxed fit. The white skirt is composed of a lightweight woven fabric with no stretch and showcases a multi-colored tropical print. Complete your look with the matching crop top!Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06301-0010
Category Name: Vacation Looks
Price: $34.90
Availability: Out of Stock
Product Badge:- Clearance
-
Living My Best Life Wrap Skirt
Live your best life in this colorful maxi skirt! It features a high rise waist, a wrap design with a high slit and a multi hued bohemian-inspired print. Skirt is composed of lightweight woven fabric that offers a relaxed fit with minimal stretch.Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 06301-0004
Category Name: Vacation Looks
Price: $4.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Lady Like Layers Kimono Cover Up
Add a chic feminine touch to your otherwise casual look with this trendy cover up. It features an embroidered mesh fabric with kimono style sleeves, a knee length, and an open front.Cover up is composed of a sheer mesh fabric that offers a relaxed fit with slight stretch.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06204-4763
Category Name: Vacation Looks
Price: $14.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Bohemian Burnout Fringe Kimono
Let your boho side show in this pretty kimono! It features a drape open front, kimono sleeves, an all over paisley burnout print and a fringe trim throughout. Kimono is composed of a lightweight woven fabric that offers a relaxed fit with a minimal stretch.
Style Number/Barcode: 06204-4751
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Fun In Fringe Lace Kimono Cover Up
Have some fun in this cover up. It features a sheer lace, open front, short kimono style sleeves, and fringe at the hemline. Cover up is composed of crochet knit fabric that offers a relaxed fit with a moderate stretch.Model is 5'7" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06204-4747
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Top It Off Chiffon Kimono Cover Up
Top off that simple yet sexy look with the perfect cover up! This black kimono style piece features an open front, short sleeves, and a waist tie belt. Chiffon fabric is light, airy, and sheer.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06204-4723
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Sheer-ly Yours Chiffon Kimono
This lovely kimono stays true to you! The cover-up features a two button closure at the waist. The kimono is composed of a sheer, unlined chiffon that has a lightweight feel.
Style Number/Barcode: 06204-4632
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Looking Like A Daydream Eyelet Lace Dress
Look like a daydream in this adorable eyelet lace mini dress for your next date. Designed with short puff sleeves and a bodycon silhouette with a ruffled hem, you'll bring flirty vibes.
Fit & Features
- Eyelet lace fabric with knit lining, moderate stretch
- Sweetheart neckline, ruched bust
- Short puff sleeves, ruffle trim
- Bodycon silhouette
- Mini-length tiered ruffled hem
- Runs true to size
Style Number/Barcode: 05102-6059
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free