Cool Weather Outfits
Cool weather outfits are your ticket to slaying every chilly-day vibe without missing a beat. Whether you’re making power moves at brunch, planning a rooftop hang with your ride-or-die crew, or just living your main character moment, these looks have your back. Get ready to layer up, turn heads, and keep the good vibes rolling—because cold days are no match for your hot style.
$52.90
A trendy olive twill crop jacket with a fleece-lined hoodie, perfect for cozy, casual nights.
$49.90
A sleek black faux leather jacket with a collared neckline and zip-up front closure.
$46.90 - $49.90
A chic olive cargo jogger with high-rise waist, metal ring trims, and elastic cuffed hems.
$39.90
A chic pair of black high-rise skinny pants in coated faux leather with minimal stretch.
$49.90
A black faux leather cropped jacket with an asymmetrical zipper and adjustable waist belt for edgy style.
$29.90
A natural oversized knit bolero with slouchy sleeves and an ultra-cropped hem for cozy layering.
$39.90
An ivory knit bolero with faux fur cuffs and collar, featuring an ultra-cropped hem and open front.
$49.90
A stylish pair of black high-rise cargo denim jeans with a straight-leg silhouette and flap pockets.
$39.90
A sleek pair of black faux leather pants with a high-rise waist and straight-leg silhouette.
$46.90
An acid-wash black denim jacket with a standing collar and cropped hem for an edgy look.
$49.90
A chic ivory faux leather jacket with striped sleeves, studded collar, and zippered pockets.
$44.90
A sleek black faux leather cropped blazer with a relaxed fit and lapel collar.
$44.90
A trendy denim moto jacket featuring a cool faded design and fitted cropped hem.
$42.90
A taupe nylon hoodie bomber jacket with a relaxed fit and drawstring hood for casual wear.
$54.90
A burgundy faux leather moto jacket featuring a belted crop hem and zippered pockets.
$59.90
A charcoal faux leather bomber jacket with a cropped oversized fit and zipper front closure.
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Layer on a chic vibe with this sleek faux leather cropped blazer. The cropped relaxed silhouette will give your 'fit that effortlessly cool look. Fit & FeaturesSmooth faux leather fabric with sleek woven lining, no stretch, Lapel collar, Long sleeves, Cropped 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 Chic Layer Faux Leather Cropped Blazer in Black | Size: S
Hop on the style train with the cool girl chic striped faux leather jacket. Rock those stripes and studded collar, zip up, and flaunt the fitted cropped hem. It's your new go-to vibe! Fit & FeaturesFaux leather fabric with smooth woven lining, no stretch, Striped design down the shoulders and sleeves, Standing collar neckline with studded detailing and button closure, Zip-front, Dual zippered lined pockets, back buckle and button strap detailing, Fitted cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cool Girl Chic Striped Faux Leather Jacket in Ivory | Size: L
Shift into glam faux leather moto jacket brings edgy vibes with its asymmetrical zipper, zippered pockets, and adjustable waist belt. Perfect for your fearless adventures! Fit & FeaturesFaux leather fabrication, woven sewn-in lining, Lapel collar, Asymmetrical zipper closure, Zippered side pockets, Long sleeves, Adjustable waist belt with metal grommets, Cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Shift Into Glam Faux Leather Moto Jacket in Black | Size: L
Serve modern iconic vibes in this oversized faux leather moto jacket with trendy belted and buckle accents and a cropped hem that flaunts your figure. Pair with jeans. Fit & FeaturesFaux leather fabric with woven lining, no stretch, Collared neckline with lapels, Zippered lined front pockets, Long sleeves, Belted accent with buckle and metal grommets, Cropped hem , Oversized fit, Free Shipping on All Orders Over $75. | Windsor Modern Icon Oversized Faux Leather Belted Moto Jacket in Ivory | Size: M
You'll be here to slay your next night out in this sleek faux leather vest. The tie-front design and fitted cropped silhouette create that snatched look. Fit & FeaturesFaux leather fabric with knit lining, minimal stretch, Sleeveless V-neckline, Tie-front design, Fitted cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Here To Slay Faux Leather Cropped Vest in Black | Size: L | Leather/Knit Fabric
Keep your fall and winter wardrobe trendy with this sleek faux leather blazer! It features a lapel collar, an open front with a single button closure, long sleeves, front pockets, and a chic oversized fit. The faux leather fabric includes a smooth lining. Style over a corset top and mini skirt. Fit & FeaturesLapel collar, Open front, single button closure, Long sleeves, Dual front pockets, Slit accent at the back, Faux leather fabric, smooth lining, no stretch, 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 Keep It Trendy Oversized Faux Leather Blazer in Brown | Size: M
Fashionable-edge combine on this faux leather vest to upgrade your concert or festival fits'! Fit & FeaturesSleek faux leather fabric, Square neckline, Wide shoulder straps, Button down front closures, Front pockets, Split center front hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Fashionable Edge Button Down Faux Leather Vest in Black | Size: M
Dare to ride in style with the ride with me faux leather moto jacket. Featuring sleek faux leather, zippered pockets, and a belted crop hem, it's your go-to for effortless cool vibes. Fit & FeaturesSleek faux leather fabric, sewn-in woven lining, Relaxed long sleeves, Lapel collar neckline, Zippered three pockets, Front zip-up closure, Belted crop hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Ride With Me Faux Leather Moto Jacket in Burgundy | Size: XS
Bold girl vibes with a zip-up twist. Rev the engine to your cool style in this faux leather moto vest designed with a vintage-inspired look and a cropped length that flaunts your edgy allure! Fit & FeaturesVintage-inspired faux leather fabric, sewn-in knit lining, Standing collar neckline with snap-button closure, Front zip-up closure, Faux chest zippered pockets, functional side zipper pockets, Cropped length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Throttle Babe Faux Leather Moto Vest in Black | Size: M | Leather/Knit Fabric
An edgy faux leather vest featuring a collared neckline, snap buttons, and front zipper closures give it a functional style while the cropped length hem keeps it modern. Fit & FeaturesFaux leather material, sewn-in woven lining, Collared neckline, Snap buttons and front zipper closures, Cropped length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Hit Your Mark Faux Leather Moto Vest in Black | Size: M
Cool Weather Outfits
When the air turns crisp and you can see your breath swirling in the morning, that’s your cue to break out the cool weather fits that make every sidewalk feel like your personal runway. This is where the art of layering becomes your secret weapon—think buttery-soft knits, plush fleece, and those oversized jackets that feel like a warm hug but look like you just stepped out of a street style shoot. The trick is all about mixing textures and stacking up layers, so you’re cozy without looking bulky. Start with a fitted base like a long-sleeve tee or a ribbed turtleneck, then add a chunky sweater or a sleek cardigan for that extra hit of warmth. Top it off with a statement coat—maybe a structured trench or a puffer that’s as bold as your group chat energy. And don’t even get us started on accessories: a slouchy beanie, a scarf with attitude, and gloves that actually let you text back fast. Boots are a must, whether you’re into ankle styles with a little heel or chunky sneakers that can handle an impromptu adventure. These staples aren’t just about staying toasty—they’re about showing off your style even when the weather tries to play games.
Cool weather outfits aren’t just for your day-to-day hustle, either. They make the ultimate gift for anyone who loves to turn heads, whether you’re shopping for your BFF who’s always cold, your sister who’s obsessed with TikTok trends, or your mom who deserves to feel like a queen on her coffee run. There’s something extra special about giving pieces that are both practical and packed with personality—think oversized cardigans for movie marathons, fleece jackets for those spontaneous road trips, or a pair of wide-leg trousers that transition from brunch to bonfire with zero effort. Layering lets you flex your creativity, mixing looser bottoms with cropped sweaters or pairing a dress with thermal tights and boots for a look that’s both effortless and unforgettable. And when plans pop up out of nowhere (because you know they always do), having a closet stocked with go-to cool weather essentials means you’re ready for anything, from late-night hangs to morning coffee runs. If you’re looking to take your style to the next level, or just want to see how the pros do it, don’t miss our curated inspo on Trendy Winter Outfits—it’s your next-level mood board for all things cozy, chic, and totally you.