Winter Night Out Outfits
Winter night out outfits are all about turning up the heat when temps drop and making every entrance unforgettable. Whether you’re hitting the hottest rooftop bar or dancing until last call, these looks are here to help you serve main character energy—no coat check required. From flirty minis to curve-hugging fits, get ready to steal the spotlight and keep your crew asking, “Where’d you get that?” Because nothing says fearless like braving the chill in style and owning every second of your night out.
$54.90
A taupe faux suede trench coat with a belted waist and double-breasted button closures.
$52.90
A brown faux suede trench coat with a tie-front belt and long-length hem.
$21.97 $49.90 56% off
A cozy camel faux suede shacket with long sleeves, button-up front, and convenient front pockets.
$59.90
A brown plaid oversized shacket in faux wool with faux suede lining and chest pockets.
$35 $49.90 30% off
A navy blue plaid shacket with faux wool fabric and a relaxed fit for casual styling.
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Seasonal Favorite Faux Suede Shacket in Camel
$21.97 $49.90
56% off
The perfect faux suede shacket for layering during the chilly seasons! It features cozy long sleeves a button-up front, and convenient front pockets to help keep your hands warm. Style with booties. Fit & FeaturesSoft faux suede lined fabric, Long sleeves, Collar neckline, Button-up front closures, Front pockets, Relaxed silhouette, Runs true to size, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Seasonal Favorite Faux Suede Shacket in Camel | Size: S
Casually cozy, this plaid woven shacket features a collared neckline, long sleeves, a button-down front with buttoned chest pockets, and a cropped cinched hem with an overall relaxed fit. Layer over a basic top with a denim skirt and booties! Fit & FeaturesPlaid woven fabric, no stretch, Collared neckline, Long sleeves with single-button detail, Button-down front, Dual buttoned chest pockets, Cropped hem, elastic cinched back hem, relaxed fit, Runs true to size, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Casually Cozy Plaid Woven Cropped Shacket in Navy Blue | Size: M | Woven Fabric
Layer on this trendy plaid shacket perfect for cozy season featuring a collared neckline, long sleeves with buttons to cuff, a complete button-down front, chest pockets, and a casually chic relaxed fit. Style with jeans and booties. Fit & FeaturesWoven fabric with buffalo plaid print, no stretch, Collared neckline, Long sleeves with single-button detail, Button-down front, Dual flap chest pockets, Long-length hem, relaxed fit, Runs true to size, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Cozy Season Plaid Button-Down Shacket in Grey | Size: L | Woven Fabric
It's the season for this plaid oversized shacket to come out and play! Keep cozy and cute in this shacket perfect for styling with boots. Fit & FeaturesFaux wool fabrication, faux suede lining, no stretch, Plaid pattern, Collared neckline, Long sleeves with single button cuff, Button-down front, Chest pockets with buttoned flap closure, Oversized fit, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Plaid Passion Oversized Faux Wool Shacket in Brown | Size: M/L | Faux Suede
Get comfy in the cozy layer plaid woven shacket! With a relaxed fit, button-down front, and chic plaid pattern, it's perfect for casual hangouts. Total vibe! Fit & FeaturesPlaid woven fabric with knit lining, minimal stretch, Collared neckline, Button-down front, Single chest pocket, Long sleeves with single-button detail, Long-length hem, relaxed fit, Runs true to size, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Cozy Layer Plaid Woven Shacket in Ivory | Size: M | Knit Fabric/Woven Fabric
Perfectly plaid woven oversized cropped shacket is your go-to for laid-back vibes. With a collared neckline, button-down front, and flap pockets, it's perfect for any chill hangout or meet-up. Fit & FeaturesPlaid woven fabric with smooth woven lining, no stretch, Collared neckline, Long sleeves with single-button detail, Complete button-down front, Flap chest pockets, Cropped hem, Oversized fit, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Perfectly Plaid Woven Oversized Cropped Shacket in Taupe | Size: S | Woven Fabric
Forever femme with endless styling options, this sheer lace long sleeve topper elevates your day-to-night look. Fit & FeaturesSheer lace fabric, moderate stretch, Fitted long sleeves, Crew neckline, Ultra-cropped length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Forever Femme Sheer Lace Long Sleeve Topper in Black | Size: M | Lace Fabric/Sheer Lace Fabric
Fit & FeaturesPlaid printed woven fabric with lining, Collared neckline, Long sleeves with single-button detail, Complete button-down front, Chest pocket, Oversized fit, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Comfy Trend Plaid Woven Oversized Shacket in Ivory | Size: L | Woven Fabric
Effortless Cutie Long Sleeve Plaid Shacket in Navy Blue
$35 $49.90
30% off
Layer on this effortlessly cute long sleeve plaid shacket perfect for pairing with a fitted top and denim jeans for everyday styling. Fit & FeaturesPlaid printed faux wool fabric, no stretch, Collared neckline, Button down front, Long sleeves with single-button detail, Dual chest pockets, Relaxed fit, Runs true to size, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Effortless Cutie Long Sleeve Plaid Shacket in Navy Blue | Size: M
Winter Night Out Outfits
When the city lights start to twinkle and the group chat is blowing up, you know it’s time to cue the glam for a night out that’s anything but ordinary. Whether you’re plotting rooftop mischief, dancing under neon lights, or making an entrance at the coziest lounge in town, your night out look is more than just an outfit—it’s your armor, your vibe, and your secret weapon all rolled into one. That’s why picking the right pieces is all about balancing your boldest self with practical magic. Think layers that serve up drama and warmth, textures that beg to be touched, and silhouettes that move with you from that first toast to the last laugh of the night. Maybe you’re the friend who always brings the sparkle, or maybe you’re the low-key legend who slays in sleek, effortless chic. Either way, the right night out ensemble lets you take on the night with confidence—no shivers, no outfit regrets, just pure main character energy. And let’s be real, these looks aren’t just for you; they’re the ultimate “I saw this and thought of you” gift for your ride-or-die, your sister, or anyone who deserves to feel unstoppable when the sun goes down.
Shopping for the perfect night out fit is a whole vibe in itself. It’s about choosing pieces that feel as good as they look—soft knits that hug you in all the right places, faux leather that brings the edge, and statement accents that catch the light (and a few glances). If you’re gifting, you’re not just giving clothes; you’re handing over a ticket to unforgettable memories, spontaneous adventures, and Insta-worthy moments. It’s the kind of gift that says, “I see you, and you’re a star.” And for those who love to switch it up, mixing and matching is the name of the game. Pair a flirty skirt with a cozy top for that “I just threw this on” perfection, or go for all-out glam with a figure-hugging dress and accessories that dial up the drama. Don’t forget the finishing touches—think bold earrings, a killer clutch, and boots that were made for strutting. Every detail matters when you’re building a look that’s as dynamic and unforgettable as the night ahead. For more inspo and to take your night out style to the next level, check out our curated Winter Party Outfit collection and get ready to turn every entrance into a moment.