Casual Thanksgiving Outfits
Casual Thanksgiving outfits are all about striking that perfect balance—cute enough for family photos, comfy enough for a second helping of pie. Whether you’re hosting the feast or just showing up with your signature side dish, you want a look that feels effortless but still put-together. Think cozy textures, relaxed fits, and just the right amount of polish to keep things interesting (and Insta-worthy). From Friendsgiving hangs to post-dinner strolls, these styles are ready for every vibe on your holiday agenda—no outfit panic necessary.
$46.90
A black high-waist cargo jogger with metal ring trims and elastic hem for a sporty look.
$20.97 $46.90 55% off
A brown woven midi dress with a ditsy floral pattern, corset bodice, and high front slit.
$59.90
An ivory plaid oversized shacket with a collared neckline and chest pocket, ideal for casual wear.
$49.90
A navy blue plaid woven shacket with a cropped hem and relaxed fit for casual style.
$36.90
A fuzzy brown rib knit crop sweater featuring a quarter zip and slouchy long sleeves.
$36.90
A brown cable knit sweater featuring a collared neckline, oversized long sleeves, and a cropped hem.
$39.90
A cozy charcoal cable knit sweater featuring an off-the-shoulder foldover neckline and fitted crop hem.
$42.90
A brown floral abstract maxi dress featuring daring cutouts, hardware trim, and a curve-hugging silhouette.
$19.97 $32.90 39% off
An ivory off-the-shoulder mini dress in striped ribbed knit offers cozy flair and stretch.
$39.90
A taupe corduroy mini skort with a belted waist, cargo pockets, and comfortable shorts lining.
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Achieve a perfectly stylish everyday look with this sleeveless ribbed knit midi dress! Designed with a comfortable ribbed knit fabric offering plenty of stretch, it features a V-neckline, spaghetti straps, a midi-length hem with a chic high front slit, and a form-hugging silhouette. Pair with a cropped denim jacket and clear mules. Fit & FeaturesStretchy ribbed knit fabric, V-neckline, Spaghetti straps, High front slit, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Perfectly Stylish Sleeveless Ribbed Knit Midi Dress in Black | Size: M | Knit Fabric
Windsor Chic Fall Vibe Ditsy Floral Corset Midi Dress in Brown
$20.97 $46.90
55% off
Channel the chic fall vibe in this ditsy floral woven midi dress featuring a sleeveless sweetheart neckline with a ruched bust and tie-front detail, thin tank shoulder straps, and a corset-style bodice. The high waist leads to a flowy A-line silhouette accented with a high-cut front slit. Fit & FeaturesDitsy floral-printed woven fabric, Sweetheart neckline, ruched bust, tie-front detail, underwire bust, Thin tank shoulder straps, Corset-style bodice with piping, high waist seam, Hidden side zipper and hook-eye closure, High front slit, Midi-length A-line fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Fall Vibe Ditsy Floral Corset Midi Dress in Brown | Size: XS | Woven Fabric
Windsor Dinner Downtown Sleeveless Ruched Midi Dress in Brown
$19.97 $32.90
39% off
The perfect chic sleeveless midi dress for grabbing dinner downtown! Crafted from smooth knit fabric, this crew neck dress boasts curve-accentuating ruched seams along the bodycon silhouette and a sleek midi-length hem. Pair with kitten heels and a clutch. Fit & FeaturesSmooth knit fabric, stretchy knit lining, Sleeveless crew neck, Side ruched seams, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Dinner Downtown Sleeveless Ruched Midi Dress in Brown | Size: XS | Knit Fabric
Show off your smooth moves in this strapless bodycon midi dress perfect for dressing up or down for any occasion! Fit & FeaturesRib knit fabric, sewn-in knit lining, moderate stretch, Strapless neckline, Side slit, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Smooth Talker Strapless Bodycon Midi Dress in Mocha | Size: M | Knit Fabric
Show off pretty vibes in this adorable layered skater dress made with breezy eyelet knit fabric. Pair with sneakers for a cute casual look or wedges for a dressier style. Fit & FeaturesStretchy sheer eyelet knit fabric, partial knit lining, Square neckline, Spaghetti straps, Double-layered skater skirt, Short fit-and-flare silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Pretty Vibes Eyelet Knit Layered Skater Dress in White-2 | Size: L | Knit Fabric
Windsor It Girl High Neck Lace Up Maxi Dress in Brown
$19.97 $46.90
57% off
That “did she just walk in?” kind of dress. The bodycon knit dress hugs in all the right places with a lace-up back that does the flirting for you. Fit & FeaturesTexture knit fabric, knit lining, High neckline, Spaghetti straps, Lace-up back, Bodycon fit, maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor It Girl High Neck Lace Up Maxi Dress in Brown | Size: S | Knit Fabric
Sleek, soft, and made to flatter. This mock neck midi dress hugs in all the right places with side ruching and a soft modal blend knit fabric that gives casual polish. Perfect for weekday styling and weekend looks! Fit & FeaturesSoft modal-blend knit fabric, knit lining, moderate stretch, Sleeveless mock neck, Side ruched seams, Bodycon fit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Curve Flow Bodycon Midi Dress in Black | Size: L | Knit Fabric
Own the spotlight on vacation in this midi dress! Featuring a bold halter neckline and an sexy open back, this dress exudes allure, while the bodycon silhouette and slit add a flattering look. Fit & FeaturesSlinky knit fabric, smooth stretchy knit lining, Halter cowl neckline, beaded spaghetti strap tie, Open back with spaghetti strap tie, Bodycon silhouette, Slit accent, midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Paradise Halter Open Back Slit Midi Dress in Red Brown | Size: L | Knit Fabric
It’s giving sleek, sculpted, and effortlessly romantic. With a knotted bust, cap sleeves, and a chic back slit, this maxi is your low-key way to steal the spotlight at brunch, cocktail receptions, or date night! Fit & FeaturesSlinky knit fabric, soft knit stretchy lining, Cap sleeves, Sweetheart knotted neckline, Form-hugging silhouette, Center back slit, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Soft Curves Ahead Cap Sleeve Maxi Dress in Black | Size: L | Knit Fabric
This isn’t just a dress, it’s a moment. With sultry cutouts, strappy details, and a leggy high slit, this curve-hugging mesh maxi brings the heat for nights out, birthdays, and turning heads on vacation! Fit & FeaturesAbstract tie-dye print, mesh fabric, sewn-in knit lining, One-shoulder neckline, bungee spaghetti strap, Side cutout, open back, High front slit, adjustable bungee cord strap with toggle, Hidden side zipper and hook-eye closure, Curve-hugging fit, maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Heat Check Abstract Cutout Maxi Dress in Blue | Size: S | Knit Fabric/Mesh Fabric/Mesh Fabric