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.
-
Off The Shoulder Floral Peplum Top
Spring forward with your wardrobe in this adorable floral printed peplum top! Pair with some light wash denim for a fresh look.
Fit & Features
- Off the shoulder elastic banded neckline
- Long sleeves | Elastic banded hems
- High rise elastic banded waist
- Wrap front peplum hem
- Lighweight, semi-sheer woven fabric
- All over floral print
Style Number/Barcode: 06003-0733
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Love The Lace Up Satin Crop Top
We know, we all are in LOVE with this lace up satin crop top! Pair with some denim for an effortless yet so trendy look!
Fit & Features
- Slight sweetheart neckline
- Long puff sleeves | Single buttons to cuff
- Lattice lace up front
- Cropped
- Sleek satin-like fabric
- Minimal stretch
Style Number/Barcode: 06003-0744
Category Name: Vacation Looks
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Falling For It Ruffled Chiffon Leopard Print Dress
Have them all falling for you when you step out in this flirty chiffon ruffled mini dress! Easily style with a pair of black mules and sweet pearl hoops!
Fit & Features
- Ruffle trim mock neckline
- Long sleeves with a ruffled wrist
- Relaxed bodice
- Stretchy smocked waist line
- Tired ruffled skirt
- Mini hemline | Lined at the skirt
- Slip on fit | No closures
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0513
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Trendy Girl Next Door Strapless Denim Mini Dress
Create a trendy girl next door vibe in this denim cargo mini dress! Made with a stretchy cotton-blend denim fabric, this dress features a strapless straight-across neckline, a secure back zipper closure, faux chest pockets, and large cargo-style flap pockets at the waist. The form-hugging silhouette will flaunt your gorgeous figure. Style this mini-length dress with cowboy boots for a country concert!
Fit & Features
- Cotton-blend denim fabric, moderate stretch
- Strapless straight neckline, front no-slip strip
- Back zipper with hook and eye closure
- Faux chest pockets
- Cargo flap pockets
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5524
Category Name: Vacation Looks
Price: $11.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Shady Business Square Oval Sunglasses
Keep it shady with this classic pair of shades that literally goes with everything!
- Square oval design
- Dainty arms
- Textured gold hardware
- 100% UV protection
Style Number/Barcode: 07008-0694
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
With Love Heart Sunglasses
Hey there miss mod! Throw on your heart shaped shades, and some red lipstick cause you're a modern day pinup doll!
- Heart shaped frame
- Cat eye corners
- Dark lenses
- 100% UV Protection
Style Number/Barcode: 07008-0695
Category Name: Vacation Looks
Price: $4.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Later Hater Square Cat Eye Sunglasses
Peace out haterrrr, we got our shades on and we cant b bothered!
- Square cat eye design
- Ombre effect
- Golden hardware
- Skinny arms
- 100% UV protection
Style Number/Barcode: 07008-0693
Category Name: Vacation Looks
Price: $5.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Heart Eyez Rimless Sunglasses
Do you have heart eyes for me or is it just your cute shades?
- Rimless design
- Rose gold hardware
- Heart shaped lenses
- 100% UV protection
- Ombre effect
Style Number/Barcode: 07008-0696
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Flower Child Rhinestone Tassel Earrings
Feeling a little boho, feeling a little glam? We got u boo! These versatile tassel earrings can be paired with nearly all looks!
- Gold flower designed post
- Rhinestone embellished
- Drop Tassel fringe
- Post back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0315
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Wide Brim Belted Panama Hat
This adorable belted panama hat screams brunch! Get totally weekend ready with this trendy hat.
- Wide brim
- Curved top
- Belted accent
Style Number/Barcode: 07302-0131
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Walks Through The Park Slide On Sandals
Whether you are walking through the park, or taking a walk on the beach these goes-with-everything slides are the perfect fit!
- Open almond toe
- Slide on design
- Narrow fit
- Faux leather
- Single band
Style Number/Barcode: 07404-0537
Category Name: Vacation Looks
Price: $9.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Paisley and Playful Halter Skater Dress
Flirty, floaty, and made for dancing under the sun. With a smocked bust and ruffled skater fit, this halter mini dress is your go-to for festivals, vacays, or just looking way too good for no reason.
Fit & Features
- Paisley print, woven fabric, bust lining
- Halter V-neckline, spaghetti strap tie
- Stretchy smocked bust
- Open tie-back detail
- Flowy skater silhouette
- Ruffled trim short hem
- Runs true to size
Style Number/Barcode: 05102-000065
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Weekend Ready Platform Sandals
Get ready to take on the weekend in these absolutley ADORABLE platform sandals! Wear them to shop, brunch, and hang with your squad!
- Open rounded toe
- Thick toe strap
- Adjustable around the ankle strap
- Open back
- Cork platform
- Textured rubber flat sole
- Faux leather straps and insole lining
Style Number/Barcode: 07404-0540
Category Name: Vacation Looks
Price: $22.90
Availability: Out of Stock
Product Badge:- Sale
-
Step It Up Block Heeled Sandals
We've found it - the it girl sandal of the season to step up your shoe game. Add to cart now, and thank us later

- Open almond toe
- Thick toe strap
- Adjustable around the ankle strap
- Open back
- Short block heel
- Faux leather straps and insole lining
Style Number/Barcode: 07404-0536
Category Name: Vacation Looks
Price: $14.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Hear Meow-Out Leopard Midi Dress
Fiercely command a room with this bold mini dress! They'll be listening to every fashion tip you got

Fits & Features
- Adjustable Spaghetti Straps Cross At Back
- Cowl Neckline I Back Zip
- Midi Length Silhouette I Side Slit
- Woven Fabric I Leopard-Inspired Print
- Relax Fit I Minimal Stretch
Style Number/Barcode: 05102-0371
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Lucky Feather Mini Hoop Earrings
Wear a pair of lucky feathers this season, whether your're at a festival, or you just feel like making a statement, these earrings are a boho dream!
- Small hoop with omega closure
- Drop bar
- Dangling large black feather
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0355
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Five Pack Ombre Stone Bobby Pins
Add some glam to your pretty tresses with this five pack of ombre stone bobby pins!
- Five pack of gold bobby pins
- Differing hued stones
- Ombre effect when all worn together
- Mauve + Clear stones
- Slide on fit
Style Number/Barcode: 07006-0108
Category Name: Vacation Looks
Price: $3.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Shine Is On Your Side Rhinestone Teardrop Barrettes
We know you love a good sparkle. Show your shine in these rhinestone barettes!
-
Set Of Three
- Wide Teardrop-Style Barette
- Adorned With Sparkling Rhinestones
Style Number/Barcode: 07006-0110
Category Name: Vacation Looks
Price: $2.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Set Of Three
-
Attention Please High-Rise Cargo Mini Skirt
Functional fashion meets a flattering silhouette with this cargo mini skirt perfect for hangs! Featuring a high-rise waist and bodycon fit, this skirt accentuates your curves. The side flap pockets and faux back pockets add a touch of utility-chic style to the twill woven fabric. Complete the look in a short sleeve tee and sneakers.
Fit & Features
- Twill woven fabric, no stretch
- High rise waist
- Front button and hidden zipper closure
- Side flap pockets, faux back pockets
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06301-0183
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Collared Button Down Shirt Dress
This classic, chic button-down shirt dress can be worn as a sexy dress or layered over an edgy 'fit!
Fit & Features
- Collared
- Long sleeves | Dual buttons to cuff
- Button down front
- Slight cinched waist
- Relaxed fit
- Woven fabric
Model is 5'8" with a 32" bust, 26" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06003-0549
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Ur On My Mind Clear Banded Mules
Every lil' thing you do, ur on my mind! Especially when you walk out in these trendsetting mules bb!
- Open almond toe
- Double clear bands
- Short block heel
- Faux nubuck material
- Slide on design
Style Number/Barcode: 07401-0586
Category Name: Vacation Looks
Price: $12.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Step By Step Wrap Sandals
Peep that pedi babe! Even though sandals are more casual, this unique design brings a little life to your everyday look! Pair with high waist shorts and a graphic tee to complete your look!
- Open almond toe
- Single band over the toe
- Strappy wrap around lace up detail
- Flat sole
Style Number/Barcode: 07404-0107
Category Name: Vacation Looks
Price: $12.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Oh My Heart Rhinestone Barrette
You are just a lil' sweetheart ain't ya? This rhinestone barrette is the cutest addition to your hair do! Simply tease your hair a little bit and then set barrette on top!
- Medium sized
- Heart outline design
- Rhinestone embellished
- Snap ball closure
Style Number/Barcode: 07006-0111
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Live Your Coziest Life Slipper Socks
Live your coziest life in a pair of comfy slipper socks boo!
- Faux fur lining
- Woven knit design
- Over the ankle fit
- Non-slip grip
- Pom-Pom accents
Style Number/Barcode: 07306-0033
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Sale