Summer Looks
Summer outfits that carry you from beach days to after-dark plans without missing a step. Matching sets keep things streamlined, while maxis, sundresses, and rompers deliver an easy, pulled-together feel, balanced by sharper staples like hot shorts, denim mini skirts, halters, and tube tops. Textures and prints stay in focus—crochet, mesh, florals, polka dots, and graphic tees—finished with sandals for a clean daytime look or styled up for wherever the night leads. From sunlit days to warm nights out, this edit moves effortlessly through vacation getaways, festivals, concerts, and GNO, blending relaxed, sun-ready pieces with elevated options for after dark.
Now Trending
Summer Outfits That Shine from Dawn to Dusk
This season’s must-have summer outfits carry you from sunrise to sunset in effortless style. Head-turning sets in bold matching prints make you the center of attention at day parties and night scenes. Brunch-ready dresses—flirty minis, midis, and maxis in breezy linen, airy cotton, and floaty chiffon—are made for café hangs and sunset selfies. Polished day-to-night vibes come through crisp linen rompers and tailored crop-and-skirt combos, keeping you sharp at the office and effortlessly chic for after-hours. Effortless essentials like graphic tees with lace shorts or lightweight crop tops paired with denim deliver stress-free style on those “too busy to think” days.
Star-spangled pieces in red, white, and blue lend a festive touch to your 4th of July looks and Labor Day outfits. For laid‑back holiday weekends, playful rompers and skorts channel joyful backyard party vibes, while tropical-print matching sets and mesh-panel tanks slide seamlessly into vacation and resort wardrobes.
Curated for vacations, getaways, and holiday trips, don't miss the latest updates to 2026 summer dress trends! Statement accessories—faux leather wedges or strappy sandals—provide the perfect finishing flourish, and Windsor’s latest summer formal dress collection offers elevated options for sunlit soirées.
Finish every look with strappy sandals or espadrille wedges and find fresh seasonal colors like coral, sage, and sky blue. Finding what to wear is even easier with Windsor's fashion blog with the latest tea on the best summer party looks!
These summer outfits flow from bright mornings to balmy evenings, making every moment inherently style‑worthy. Ready to build your ultimate warm‑weather wardrobe? Explore Windsor’s full edit of summer outfits—online, in‑app, or at your nearest Windsor store. Your new go‑to look awaits!
-
Sweetly Tied Skater Dress
Sweeten up your look with this adorable red skater dress! It features a sleeveless bodice, adjustable halter straps that lead to a button back closure with a keyhole cut out below, a back zipper and hook and eye closure, a V neckline, a cute tie front detail, and a flowy skater skirt. The dress is composed of a lightweight linen fabric with a short knit lining.
Style Number/Barcode: 05102-3826
Category Name: Summer Looks
Price: $13.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Totally Twirl-Worthy Skater Dress
Make sure your entrance is a twirl-worthy one in this adorable skater dress! It features a sleeveless bodice, spaghetti straps, a V neckline with lattice detailing, a back zipper and hook and eye closure, a high waist seam, and a flowy, skater skirt. The dress is composed of a ponte knit fabric with moderate stretch.
Style Number/Barcode: 05101-8804
Category Name: Summer Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Sound The Horn Trumpet Dress
Make an eye-catching style statement in this chic, curve-hugging midi dress. It features a sleeveless V-neckline, adjustable spaghetti straps for a customized fit, a flattering empire waist, and a high-low trumpet hem with a form-hugging silhouette. The dress is composed of a smooth knit fabric with a pretty sheer crochet overlay. Complete the look with cute heels.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Hidden back zipper, hook and eye closure
- Empire waist, slim-fit, high-low trumpet hem
- Sheer crochet overlay, knit fabric lining
- Curve-hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-0153
Category Name: Summer Looks
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Love Bud Sweetheart Dress
Hey sweetheart, Hey love bud , Hey little cutie ! The dress features a sweetheart neckline , tie yourself ribbon spaghetti straps, and a built in wire for a bra-like effect. The back-line of this dress is square and includes a hidden zipper. The bodice of this dress is a body con style that is form fitting and shows off those curves and has a mini slit at the hem. The dress is composed of a canvas material that offers moderate stretch. Muah!
Style Number/Barcode: 05102-0219
Category Name: Summer Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Ria Heat Stone Formal Mini Dress
Special Occasion
The Ria dress brings the sparkle to your special evening! Shimmer from the moment you enter the room in a dress that showcases your glamorous taste. The Ria dress features glitzy heat stones, sheer mesh long sleeves to show off a hint of skin, and a curve-hugging mini-length silhouette. Complete your special evening outfit with chrome heels for maximum shine.Fits & Features
-
V-neckline
- Unlined, fitted long sleeves
- Mini length silhouette
- Lined mesh fabric adorned with heat stones
- Curve hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05001-3979
Category Name: Summer Looks
Price: $29.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
V-neckline
-
Sweet As Pie Skater Dress
Honey you will look sweet as pie in this cute skater dress! This piece features a V neckline, spaghetti straps, a skater style skirt, and the best part...It has pockets! This dress is comprised of a soft crepe material that offers moderate stretch.Style Number/Barcode: 05101-8838
Category Name: Summer Looks
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Anything But Basic Maxi Dress
This sophisticated, streamlined maxi will more than earn its place in your closet this season. Chic and versatile, it goes pretty much anywhere you do! Dress features a square neckline, all-over rib knit detail, crisscross spaghetti straps, adjustable keyhole tie detail, back cutout, and side slit. Dress is partially lined and made from a soft, densely knit material with moderate stretch.
Style Number/Barcode: 05102-0012
Category Name: Summer Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Cassandra Floral Chiffon Gown
Special OccasionTake our breathe away in our beautiful mauve toned Cassandra Floral Gown! She features a cross over V neckline and ruffle spaghetti straps that are adjustable. The v style back line has matching material buttons and a hook closure. Long, floor-length skirt offers a flowy fit and includes a short skirt lining. Dress is composed of a semi-sheer floral chiffon fabric with no stretch.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-6741
Category Name: Summer Looks
Price: $29.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Alicia Formal Sleeveless Midi Dress
Special OccasionRadiate elegance in our sleek Alicia dress! She features a sleeveless bodice, a plunging V neckline, a bar strap accent and a midi length silhouette. She is composed of a lined crepe fabric that offers a form hugging fit with a moderate stretch.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-4128
Category Name: Summer Looks
Price: $29.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
City Brights Mini Dress
Get out and get glowing in this vibrant mini! Team it with a denim jacket or blazer for maximum impact. Dress slips on and features a square neckline and spaghetti straps. Dress is made from a soft, crepe-like woven material with moderate stretch.
Style Number/Barcode: 05103-0123
Category Name: Summer Looks
Price: $10.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Fresh Cut Asymmetrical Dress
This dress will always make the cut! Dress features a deep V neckline with a V wire, spaghetti straps, a hidden back zipper closure, side cut outs under the bust, ruching on one side, and a wrap skirt that creates an asymmetrical hem. Dress is composed of an unlined crepe fabric that offers a moderate stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05103-3602
Category Name: Summer Looks
Price: $10.00 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Layered In Lace Skater Dress
Layer up in lace for a charming look! This dress features a plunging V neckline with a scalloped lace trim, adjustable narrow straps that lead to a cross back design and a floral lace bodice. The flared skater skirt features a double layer design to create a head turning moment. Dress is composed of a lined crepe fabric that offers a form hugging fit with a moderate stretch.Style Number/Barcode: 05101-8796
Category Name: Summer Looks
Price: $9.97 $47.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Lace Stunner Layered Skater Dress
Stun in lace as you make a gorgeous impression! The dress features a sleeveless bodice, a V neckline, a lined floral lace bodice and adjustable narrow cross straps. The slim fit bodice leads to a double layered skater skirt. Dress is composed of a lined chiffon 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: 05101-8745
Category Name: Summer Looks
Price: $15.00 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Flower Power Chiffon Maxi Dress
Power through the day with gorgeous florals! This navy blue maxi dress features a sleeveless bodice, a V neckline with narrow straps, princess seams and a waistband accent. The back features an unlined floral lace accent with an open lower back. The slim fit bodice leads to a flowing carefree maxi length. The all over navy blue hue is accented with a teal hued floral design. Dress is composed of a slightly sheer chiffon fabric that offers a relaxed fit with minimal stretch. Includes thin knit lining.Model is 5'7" with a 32.5" bust, 22.5" waist and 34.5 hips. She is wearing a size small.
Style Number/Barcode: 05101-0019
Category Name: Summer Looks
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Wrapped In Florals Maxi Dress
Wrap yourself in pretty florals to spring into the season! This ivory maxi dress features a sleeveless bodice, a plunging V neckline, narrow adjustable straps and a cinching tie waist belt. The floor length maxi skirt features a high slit and a mini skirt length knit lining. The all over floral print features blue and pink hues for a pretty look! Dress is composed of a lined lightweight woven fabric that offers a relaxed fit with minimal stretch. Includes a back zipper closure.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-8609
Category Name: Summer Looks
Price: $22.97 $55.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Sealed With Style Tie-Waist Pants
Create a polished look in these high-waist pants with a matching tie-front belt. These dressy crepe pants are the perfect versatile style that takes you from the office to cocktail hour. This elevated high-waist pant features a self-tie belt that cinches at the waist, and a slightly flared-leg silhouette for the perfect finishing touch. Seal the perfect polished look with a long-sleeve blouse bodysuit and blazer or swap out the top for a sexy bustier for a sexy night-out look.
Fit & Features
- High-rise waist
- Tie-front accent
- Wide pant legs with a flared hem
- Crepe fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 06502-1849
Category Name: Summer Looks
Price: $15.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Plus Flowy Floral Maxi Dress
Spring into gorgeous florals in this sweetly inspired maxi dress! It features an off the shoulder neckline, a smocked bodice, short sleeves and a wrapped maxi silhouette. The all over floral print features pretty flowers throughout with foliage. Dress is composed of an hued slightly sheer woven fabric that offers a relaxed fit with minimal stretch. Includes a mini skirt length knit lining.Model is 5'9" with a 44" bust, 37" waist and 47" hips. She is wearing a size 1X
Style Number/Barcode: 15102-0022
Category Name: Summer Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Plus Basic Essentials Midi Dress
Sometimes less is more! This basic red midi dress can be kept casual or paired with accessories to dress it up! Throw on your favorite sunnies or wide brimmed hat to achieve beach worthy vibes! This dress features a scoop neckline, narrow shoulder straps and a soft to the touch fabric feel creating a curve hugging fit with plenty of stretch.
Style Number/Barcode: 15102-0020
Category Name: Summer Looks
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Plus Floral Fiesta Maxi Dress
This beautiful floral maxi dress is perfect for your spring and summer occasions! It features a stretchy off the shoulder neckline with a ruffle pop over, a stretchy high waist seam, and a flowy floor-length skirt. Dress is composed of an unlined crepe fabric with no stretch.Model is 5'8 with a 42" bust, 35" waist, and 45" hips. She is wearing a size 1X.
Style Number/Barcode: 15102-0033
Category Name: Summer Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Plus The Floral Treatment Dress
Give yourself the floral treatment in this darling dress! It features a sleeveless bodice with a square neckline, narrow shoulder straps leading to a square back, a subtle yet flattering empire waist seam, and a body-hugging fit throughout. Dress is composed of a thick, scuba knit fabric with a moderate stretch.Model is 5'11 with a 38" bust, 37" waist, and 48.5" hips. She is wearing a size 1X.
Style Number/Barcode: 15101-0078
Category Name: Summer Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Sleek Style Ribbed Midi Dress
Keep it sleek and stylin' with this yellow ribbed midi dress! It features a deep round neckline, spaghetti straps, and a traditional midi length. Ribbed knit offers plenty of curve hugging stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06005-6284
Category Name: Summer Looks
Price: $36.90
Availability: Out of Stock
Product Badge:- Clearance
-
Crochet Babe Tunic
All you need is sand and sun with this peach crochet tunic! It has a deep V neckline, lined cups, adjustable shoulder straps leading to a low square back, an exposed silver zipper closure, and a comfortable slim fit.Tunic is composed of an unlined crochet fabric 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: 06005-6289
Category Name: Summer Looks
Price: $5.00 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Take A Snap Button Midi Dress
You'll want to take tons of snaps for the gram in this button down midi dress! It features a sleeveless bodice, tank-like shoulder straps, gold faux snap buttons, a front slit, and a midi length. The black dress is composed of a ribbed knit fabric with plenty of stretch.Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.
Style Number/Barcode: 06005-6300
Category Name: Summer Looks
Price: $36.90
Availability: Out of Stock
Product Badge:- Clearance
-
Can't Relate Henley Mini Dress
Basic? Sorry can't relate. Stand out in this natural mini dress that features a sleeveless bodice, a sweetheart neckline, a multi button down front with wooden buttons, wide shoulder straps and a mini length silhouette. Dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06001-1279
Category Name: Summer Looks
Price: $22.00 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance